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Upwork Inc.

upwk · NASDAQ Industrials
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Ticker upwk
Exchange NASDAQ
Sector Industrials
Industry Staffing & Employment Services
Employees 600
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FY2021 Annual Report · Upwork Inc.
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Annual
Report
2021

Message from 
Hayden Brown

President
& CEO

Dear Stockholders,

2021 was another year of exciting change for Upwork and the global 
workforce. Companies and the talent on which they rely are radically 
reimagining not only where, when, and how work gets done, but also 
who does it and why. 

Businesses are embracing remote and hybrid work models to a 
greater degree than ever before—some out of necessity and others 
because they see the benefits on the quality, diversity, productivity, 
and morale of their talent pools. Workers are flexing newfound power 
in a tightening labor market. The Great Resignation signals their desire 
to pursue career paths that provide greater fulfillment, including those 
that don’t neatly align with historical definitions of either “full time” 
or “freelance.” This reassessment of work—a movement we call the 
Work Awakening—is gaining momentum. 

We’ve anticipated the Work Awakening, and Upwork is in a unique 
position to accelerate it.

For more than 20 years, we have been a place for companies and 
talent to connect, build lasting relationships, and collaborate on 
meaningful work in ways that challenge traditional workforce models.1 
Over that time, more than $15 billion in economic activity has occurred 
on our work marketplace.2 Last year alone, nearly three-quarters of a 
million clients got work done through Upwork. 

We are at the forefront of the changing world of work, and we 
understand it like few others do. In 2021, to respond to the growing 
needs of our talent and clients, we launched a suite of offerings to 
complement our Talent Marketplace™. These product and feature 
enhancements included Project Catalog™, Talent Scout™, and 
Virtual Talent Bench™, all of which enable companies to access new 
operating models and talent and explore emerging ways of working. In 
2022, we expect to maintain our ambitious schedule of innovation so 
that Upwork continues to flex and grow with workers and businesses 
as their needs and desires change.

1 Upwork was formed when two of the earliest innovators in the space, and the largest    
    online talent marketplaces at the time, Elance, Inc., which we refer to as Elance, and   
    oDesk Corporation, which we refer to as oDesk, combined in 2014.
2 As measured by lifetime talent earnings, including on Elance and oDesk.

More than anything, what Upwork offers is potential: the potential for 
talent on our platform to build thriving careers doing work they love, 
and the potential for businesses to grow and innovate by accessing a 
global talent pool. Our record financial performance in 2021 and the 
growing number of clients and professionals who have found a home 
on our platform are proof that we are delivering on this promise. 

With that promise in mind, the idea that people in parts of Eastern 
Europe would be unable to unlock their potential through Upwork 
because of the Russian invasion of Ukraine, associated sanctions, 
and isolation from the global community, is an affront to our core 
beliefs and the business we have built. That’s why our March 2022 
decision to suspend operations in Russia and Belarus was so difficult 
and heartbreaking. Still, I’m incredibly proud of and inspired by what 
Upwork team members across the world—including many within 
the conflict region—have done to support the safety, security, and 
well-being of talent, clients, and fellow colleagues impacted by the 
war. We look forward to a day when peace, stability, and conditions are 
restored so that we may return to Russia and Belarus and carry out 
our mission of creating economic opportunity for everyone. 

2022 will no doubt bring more change. Regardless of what lies ahead, 
we are confident that we have a winning strategy of innovating, 
evangelizing, and scaling the world’s work marketplace. In many ways, 
Upwork is just getting started. Our ambitions are bigger than ever, and 
our time is now. 

Thank you to all of our investors and Upwork team members around 
the world who are on this journey with us.

Sincerely,

Hayden Brown
President and Chief Executive Officer

Our mission is
to create economic 
opportunities so people 
have better lives.

ANNUAL REPORT 2021 

Gross Services Volume

Skills

$3.5B

10K+

Fortune 100 Companies

Categories of Work

30%+

90+

Countries

180+

The World’s Work  
Marketplace

Gross services volume is for the year ended December 31, 2021. 
Percentage of Fortune 100 companies, countries, skills, and categories  
of work are as of December 31, 2021.

ANNUAL REPORT 2021 

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

_____________________________

FORM 10-K

_____________________________

(Mark One)

☒    ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the fiscal year ended December 31, 2021

OR

☐    TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the transition period from _______ to _______

Commission File Number 001-38678

_____________________________

UPWORK INC.

(Exact name of registrant as specified in its charter)

_____________________________

Delaware
(State or other jurisdiction of incorporation or organization)
475 Brannan Street, Suite 430
San Francisco, California
(Address of principal executive offices)

46-4337682
(I.R.S. Employer Identification No.)

94107
(Zip Code)

Title of Each Class
Common Stock, $0.0001 par value per share

(650) 316-7500

(Registrant’s telephone number, including area code)

_____________________________

Securities registered pursuant to Section 12(b) of the Act:
Trading Symbol
UPWK

Securities registered pursuant to Section 12(g) of the Act:

None

_____________________________

Name of Each Exchange on Which Registered

The Nasdaq Stock Market LLC

Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act. Yes x No ☐

Indicate by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act. Yes ☐ No x

Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the
registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes x No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months
(or for such shorter period that the registrant was required to submit such files). Yes x No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,”
“accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer

Non-accelerated filer

x

☐

Accelerated filer

Smaller reporting company

Emerging growth company

☐

☐

☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section
13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal control over financial reporting under Section 404(b) of the Sarbanes-Oxley
Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report. ☒

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐ No x

The aggregate market value of voting stock held by non-affiliates of the registrant, as of June 30, 2021, the last business day of the registrant’s most recently completed second quarter, was $6,809,077,335 (based on the
closing price for shares of the registrant’s common stock as reported by The Nasdaq Global Select Market on that date).

As of January 31, 2022, there were 129,215,625 shares of the registrant’s common stock outstanding.

DOCUMENTS INCORPORATED BY REFERENCE

Portions of the registrant’s definitive proxy statement for its 2022 Annual Meeting of Stockholders, or Proxy Statement, to be filed within 120 days after the end of the fiscal year covered by this Annual Report on Form 10-K, are
incorporated by reference in Part III. Except with respect to information specifically incorporated by reference in this Annual Report, the Proxy Statement shall not be deemed to be filed as part hereof.

TABLE OF CONTENTS

Special Note Regarding Forward-Looking Statements

PART I

Item 1.

Item 1A.

Item 1B.

Item 2.

Item 3.

Item 4.

PART II
Item 5.

Item 6.

Item 7.

Business

Risk Factors

Unresolved Staff Comments

Properties

Legal Proceedings

Mine Safety Disclosures

Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities

[Reserved]

Management’s Discussion and Analysis of Financial Condition and Results of Operations

Item 7A.

Quantitative and Qualitative Disclosures About Market Risk

Item 8.

Item 9.

Financial Statements and Supplementary Data

Changes in and Disagreements With Accountants on Accounting and Financial Disclosure

Item 9A.

Controls and Procedures

Item 9B.

Item 9C.

PART III

Item 10.

Item 11.
Item 12.

Item 13.

Item 14.

PART IV

Item 15.

Item 16.

Signatures

Other Information

Disclosure Regarding Foreign Jurisdictions that Prevent Inspections

Directors, Executive Officers and Corporate Governance

Executive Compensation

Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters

Certain Relationships and Related Transactions, and Director Independence

Principal Accountant Fees and Services

Exhibits and Financial Statement Schedules

Form 10-K Summary

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Unless otherwise expressly stated or the context otherwise requires, references in this Annual Report on Form 10-K, which we refer to as this Annual Report or report, to “Upwork,”
“Company,” “our,” “us,” and “we” and similar references refer to Upwork Inc. and its wholly-owned subsidiaries.

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

This Annual Report contains forward-looking statements within the meaning of the federal securities laws. All statements contained in this Annual Report, other than statements of
historical  fact,  including  statements  regarding  our  future  operating  results  and  financial  position,  our  business  strategy  and  plans,  potential  growth  or  growth  prospects,  active
clients, future research and development, sales and marketing and general and administrative expenses, provision for transaction losses, our objectives for future operations, and
potential impacts of the ongoing COVID-19 pandemic, or expectations regarding actions we may take in response to the pandemic, are forward-looking statements. Words such as
“believes,” “may,” “will,” “estimates,” “potential,” “continues,” “anticipates,” “intends,” “expects,” “could,” “would,” “projects,” “plans,” “targets,” and variations of such words and similar
expressions are intended to identify forward-looking statements.

We have based these forward-looking statements largely on our current expectations and projections as of the date of this filing about future events and trends that we believe may
affect  our  financial  condition,  results  of  operations,  business  strategy,  short-term  and  long-term  business  operations  and  objectives,  and  financial  needs.  These  forward-looking
statements are subject to a number of risks, uncertainties and assumptions, including those described in Part I, Item 1A, “Risk Factors” in this Annual Report and the impact of the
ongoing COVID-19 pandemic. Readers are urged to carefully review and consider the various disclosures made in this Annual Report and in other documents we file from time to
time with the Securities and Exchange Commission, which we refer to as the SEC, that disclose risks and uncertainties that may affect our business. Moreover, we operate in a very
competitive and rapidly changing environment. New risks emerge from time to time. It is not possible for us to predict all risks, nor can we assess the impact of all factors on our
business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements we may
make. In light of these risks, uncertainties, and assumptions, the future events and circumstances discussed in this Annual Report may not occur and actual results could differ
materially and adversely from those anticipated or implied in the forward-looking statements.

You should not rely upon forward-looking statements as predictions of future events. The events and circumstances reflected in the forward-looking statements may not be achieved
or occur. Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee future results, performance, or achievements.
In addition, the forward-looking statements in this Annual Report are made as of the date of this filing, and we do not undertake, and expressly disclaim any duty, to update such
statements for any reason after the date of this Annual Report or to conform statements to actual results or revised expectations, except as required by law.

You should read this Annual Report and the documents that we reference herein and have filed with the SEC as exhibits to this Annual Report with the understanding that our actual
future results, performance, and events and circumstances may be materially different from what we expect.

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PART I

Item 1. Business.

Overview

We operate the world’s largest work marketplace that connects businesses, which we refer to as clients, with independent talent, as measured by gross services volume, which we
1
refer to as GSV.

Independent talent on our work marketplace, which we refer to as talent, and, together with clients, as users, includes independent professionals and agencies of varying sizes and
is an increasingly sought-after, critical, and expanding segment of the global workforce. We define clients as users that work with talent through our work marketplace. During the
year ended December 31, 2021, our work marketplace enabled $3.5 billion of GSV.

For talent, we serve as a powerful marketing channel to find rewarding, engaging, and flexible work. Talent benefits from access to quality clients, simplified invoicing, and secure
and timely payments while enjoying the freedom to run their own businesses, create their own schedules, and work from their preferred locations. Moreover, talent has real-time
visibility into opportunities that are in high demand, so that they can invest their time and focus on developing sought-after skills.

For clients, our work marketplace provides fast, secure, and efficient access to high-quality talent with over 10,000 skills across over 90 categories, such as sales and marketing,
customer service, data science and analytics, design and creative, and web, mobile, and software development. We offer a direct-to-talent approach as an alternative to traditional
intermediaries such as staffing firms, recruiters, and agencies by providing high-quality independent talent and features that help build trusted relationships and instill trust in remote
work,  including  the  ability  to  engage  talent  as  either  independent  contractors  or  as  employees  of  third-party  staffing  providers.  Our  work  marketplace  also  enables  clients  to
streamline  workflows,  such  as  talent  sourcing,  outreach,  and  contracting.  In  addition,  our  work  marketplace  provides  clients  with  access  to  essential  functionality  for  remote
engagements  with  talent,  including  communication  and  collaboration,  the  ability  to  receive  all  talent  invoices  through  our  work  marketplace,  and  payment  protection.  Our  clients
range in size from small businesses to Fortune 100 companies.

We believe that a key differentiator and driver of our growth is our track record of creating trust and enabling our users to successfully connect at scale. As the world’s largest work
marketplace that connects businesses with independent talent, as measured by GSV, we benefit from network effects that drive growth in both the number of clients posting jobs
and the number of talent seeking work. Our growth is driven by long-term and recurring use of our work marketplace by our users.

We  generate  revenue  from  both  talent  and  clients,  with  a  majority  of  our  revenue  generated  from  service  fees  charged  to  talent  for  access  to  our  work  marketplace.  We  also
generate revenue from fees charged to both clients and talent for other services, such as for transacting payments through our work marketplace, premium offerings, purchases of
“Connects” (virtual tokens that allow talent to bid on projects on our work marketplace), foreign currency exchange when clients choose to pay in currencies other than the U.S.
dollar, and our Upwork Payroll offering. In addition, we provide a managed services offering where we engage talent to complete projects, directly invoice the client, and assume
responsibility for work performed.

COVID-19 Impact on Our Business

The ongoing COVID-19 pandemic and the resulting restrictions intended to prevent its spread have continued to accelerate the secular shift toward remote and independent work.
As a result of our unique, remote-based business model, the pandemic has not impacted our clients’ access to highly-skilled talent to complete short- and long-term projects on our
work marketplace. In 2021, we prioritized our advertising, marketing, and product development efforts to reach those new and existing clients seeking to engage remote talent in
light of the shift toward remote work, due in part to the COVID-19 pandemic. As a result of these efforts, our 2021 results were fueled by both existing and new clients, who used
Upwork to address their changing business needs. We expect our business to continue to grow over time, and while we have not incurred significant disruptions to our business
thus far from the COVID-19 pandemic, we are continuously evaluating the nature of, and extent to which, the ongoing pandemic will impact our business, operating results, and
financial condition. For a more detailed discussion of the potential impact of the COVID-19 pandemic, the associated economic disruptions, and the actual operational and financial

1
 GSV represents the total amount that clients spend on both our marketplace offerings and our managed services offering as well as additional fees we charge to talent for other services. For additional information related to
how we calculate GSV, see the section titled “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Overview—Business” and “—Key Financial and Operational Metrics.”

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impacts that we have experienced to date, see the section titled “Management’s Discussion and Analysis of Financial Condition and Results of Operations.”

Our Work Marketplace

We  operate  the  world’s  largest  work  marketplace  that  connects  businesses  with  independent  talent,  as  measured  by  GSV.  We  believe  the  following  core  aspects  of  our  work
marketplace provide us with a competitive advantage:

Trusted Work Marketplace

Our  work  marketplace  fosters  trust  and  credibility  among  talent  and  clients,  while  reducing  the  friction  associated  with  searching  for,  contracting  and  collaborating  with,  and
paying highly-skilled independent talent for short-term and longer-term projects. We use a combination of the latest technology, data science, product features, and our skilled
team to position our work marketplace as a trusted online marketplace to get work done. We build and use software to highlight relevant talent, facilitate security and identity
verification for account ownership, and flag suspicious posts. We provide clients with tools to validate work performed by talent and to provide both public and private feedback
once the work is completed. Our feedback system enables talent to build their business reputation by establishing long-term credibility with project review and verified client
feedback. Talent profiles also include data from their work history on our work marketplace, including client feedback, number of hours billed, projects completed, and amount
earned. This validated expertise is a critical factor to build trust and promote brand loyalty, giving clients confidence in hiring talent for their next project. Additionally, we provide
escrow services to help ensure that clients on our work marketplace only pay for work that has been completed and talent is paid by their clients in full and on time.

Proprietary Data Drives Increasing Efficiencies

We  have  built  an  expansive  and  unique  repository  of  data  on  our  work  marketplace.  Our  proprietary  database  maintains  detailed  and  dynamic  information,  including  skills
provided by talent, feedback, and success indicators of talent and clients transacting on our work marketplace. Using this data in our machine learning algorithms enables us to
provide a trusted, convenient, and effective experience for both new and existing users and enables clients to better connect with available talent for their projects. Moreover,
our  machine  learning  algorithms  leverage  our  closed-loop  transaction  data  on  millions  of  completed  projects.  The  large  volume  of  transactions  on  our  work  marketplace
positions us to improve the effectiveness of our search algorithms and product features.

Robust Functionality

Our  work  marketplace  includes  a  proposal  tracking  system,  search  engine  and  collaboration  functionality,  artificial  intelligence-driven  talent  matching  and  proposal  ranking
capabilities, time tracking and invoicing systems, and payments services. The robust functionality of our work marketplace is designed to enable talent to more easily run their
businesses and clients to find and work with high-quality talent on a global scale.

Powerful Global Network Effects

We  have  heavily  invested  in  building  a  robust  work  marketplace  with  features  and  functionalities  to  connect  talent  and  clients  at  scale.  We  believe  our  work  marketplace
provides a strong value proposition for both clients and talent and our scale creates powerful network effects that strengthen our competitive position. In turn, as more clients
use and post projects on our work marketplace, we are able to attract more talent. As a result, we have been able to scale our business and our global community of users
efficiently and without the need for local physical presence.

Business Model with Strong Retention Metrics

The growth of our business is driven by long-term and recurring use of our work marketplace by talent and clients, which leads to increased revenue visibility. In addition, we
believe the scale of our work marketplace incentivizes talent to build their business reputations on, and continue to use, our work marketplace.

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Our Offerings

We have marketplace offerings and a managed services offering. Our marketplace offerings include Upwork Basic, Upwork Plus, Upwork Enterprise, and Upwork Payroll.

Upwork Basic

Our  Upwork  Basic  offering  provides  clients  with  access  to  independent  talent  with  verified  work  history  on  our  work  marketplace  and  client  feedback,  the  ability  to  instantly
match with the right talent, and built-in collaboration features.

Upwork Plus

Our Upwork Plus offering is designed for teams looking to stand out to quality talent and scale hiring quickly. In addition to receiving all the product features of Upwork Basic,
Upwork Plus clients can access personalized assistance, whether strategic or job-specific. They also receive perks such as a verified client badge and highlighted job posts,
which stand out to top talent and help clients achieve results.

Upwork Enterprise

Our Upwork Enterprise offering is designed for larger clients with at least 250 employees. Upwork Enterprise clients receive all the product features of Upwork Plus, in addition
to  consolidated  billing  and  monthly  invoicing,  a  dedicated  team  of  advisors,  detailed  reporting  with  company  insights  and  trends  to  enable  clients  to  hire  faster  and  more
successfully, and the opportunity for clients to onboard pre-existing independent talent onto our work marketplace. Upwork Enterprise also offers access to additional product
features, premium access to top talent, professional services, and payment terms flexibility. Additionally, through our enterprise compliance offering, clients can engage us to
determine whether talent should be classified as an employee or an independent contractor based on the scope of talent services agreed between the client and talent and
other factors.

Upwork Payroll

Our Upwork Payroll offering, one of our premium offerings, is available to clients when they choose to work with talent they engage through Upwork as employees. With Upwork
Payroll, clients have access to third-party staffing providers to employ their workers so that they can meet their talent needs through our work marketplace.

Managed Services

Through our managed services offering, we engage talent directly or as employees of third-party staffing providers to perform services for clients on our behalf, directly invoice
the client, and assume responsibility for work performed.

Escrow Services

We are licensed as an internet escrow agent by the California Department of Financial Protection and Innovation, which we refer to as the DFPI. Pursuant to applicable regulations,
funds that we hold on behalf of users are held in our escrow account and are released only according to escrow instructions that have been agreed upon by users. For fixed-price
contracts, the client deposits funds that are held in escrow, in whole or by milestone, before talent starts work. The escrow funds are then released to talent upon completion of a
project or a milestone. For hourly contracts, talent submits their billings to their clients on a weekly basis on Sunday, at which point the funds are placed in escrow. The client has
several  days  to  review,  after  which  the  funds  are  then  released  to  talent,  unless  the  client  files  a  dispute.  We  have  a  dedicated  team  focused  on  facilitating  a  resolution  of  any
disputes between talent and clients over funds held in escrow.

Our Team and Culture

Our mission—to create economic opportunities so people have better lives—is integral to our culture and how we build amazing teams and products to lead our industry. We enable
remote  work  not  only  through  our  work  marketplace  for  our  users,  but  also  for  our  own  team  members  for  whom  we  are  proud  to  offer  a  remote-first  work  model,  which  has
environmental,  as  well  as  other  benefits.  Our  team  consists  of  independent  talent  that  we  engage  through  our  work  marketplace,  corporate  employees,  and  advisors.  Our  team
members are distributed around the world, and while we have corporate offices, we do not solely rely on in-person collaboration. Our team works with a variety of tools and has
adopted practices to ensure all voices are heard, innovation is fostered, and results are achieved. Our hybrid team, and its belief in our mission, values, and vision is critical to our
success. With the consistent investment in the development of our team and our commitment to diversity, inclusion, and belonging, we cultivate an environment where people are
able to be themselves at work and perform to the best of their abilities.

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Our People

Our mission not only drives the creation and continuous development of our work marketplace, but it is also integral to how we engage our employees and our approach to
creating and fostering an inclusive environment that promotes and encourages diversity, inclusion, belonging, career development, and wellness. As of December 31, 2021, we
had approximately 650 employees, and throughout 2021, we engaged approximately 1,800 independent team members through our work marketplace to provide services to us
on a variety of internal projects. None of our team members are represented by a labor union or are covered by a collective bargaining agreement. We believe the positive
relationship between us and our team members and our unique, strong culture differentiate us and are key drivers of our business success.

Diversity, Inclusion, and Belonging

We put our people and their experiences first. We view belonging as a feeling, inclusion as a practice, and diversity as an outcome.

We foster belonging through our Upwork Belonging Communities—employee resource groups that build empathy and promote inclusive skill-building. We cultivate inclusion by
equipping  managers  with  tools  to  effectively  build  and  lead  amazing  and  inclusive  teams  that  amplify  team  members’  voices.  Additionally,  we  practice  multi-dimensional
compensation  and  mobility  reviews  during  our  semi-annual  employee  performance  evaluation  process.  This  is  led  by  a  cross-functional  team  of  human  resource  and  legal
leaders  to  help  ensure  we  are  fair  in  our  rewards  and  recognition  strategy.  To  bolster  our  diversity,  inclusion,  and  belonging  efforts,  we  also  conduct  an  internal  review  to
facilitate equity in internal mobility practices throughout the Company as an ongoing priority. Diversity, inclusion, and belonging is a journey, not a destination, and, as such, we
will continue to explore ways to cultivate an inclusive culture where every team member belongs.

Training and Development

As  an  organization  built  on  talent  and  skills  development,  we  understand  the  value  of  providing  our  employees  with  ongoing  professional  development  and  leadership
opportunities so that they can advance their careers. Led by our dedicated learning and development team, we offer our team members an array of learning and development
opportunities, including a variety of training sessions and workshops.

Benefits and Competitive Compensation

Beyond  our  training  and  development  efforts,  we  take  pride  in  offering  competitive,  market-based  compensation  and  benefits  to  our  employees.  We  engage  compensation
consultants  to  benchmark  our  employee  compensation  with  external  sources  to  ensure  fair  and  equitable  pay  practices,  and  utilize  equity  grants  to  align  employee
compensation  with  stockholder  interests.  Merit  increases  and  promotions  are  awarded  based  on  an  individual’s  impact  within  the  organization  and  an  established  business
need, and in consideration with market data. Knowing our employees have diverse needs and life priorities, we also provide expanded benefits to those eligible, which include
core benefits such as medical, dental, vision, and disability insurance, in addition to benefits tailored to the specific needs of our employees, such as mental health, fertility,
family back-up care, and adoption support.

Team Member Feedback

We  engage  our  workforce  in  meaningful  ways  and  take  timely  action  in  response  to  their  feedback.  While  our  culture  and  engagement  process  starts  during  the  new  team
member onboarding process, one way we sustain our feedback loop is via an industry-recognized team member engagement platform. Through the platform, we survey our
team  members  on  a  regular  basis  to  gather  feedback.  In  2021,  our  average  employee  response  rate  was  86%,  and  we  received  notably  high  scores  with  respect  to  our
leadership  and  purpose,  with  the  survey  results  reflecting  that  many  team  members  feel  invested  in  our  future  and  continue  to  regard  Upwork  as  a  workplace  they  would
recommend  to  others.  In  these  surveys,  team  members  also  consistently  recognize  our  efforts  to  cultivate  an  inclusive  workplace.  Responses  to  these  surveys  and  other
employee feedback guide our team engagement efforts. We believe that ensuring that our people feel valued, supported, and heard helps us attract, retain, and develop the
right talent to lead the Company and successfully execute our corporate strategy.

Employee Wellness

Employee safety and well-being is of paramount importance to us in any year and continued to be of particular focus in 2021 in light of the COVID-19 pandemic. We provide
productivity and collaboration tools and resources for employees, including training and toolkits to help leaders effectively lead and manage remote teams. In

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addition,  we  enhanced  and  promoted  programs  to  support  our  employees’  physical,  financial,  and  mental  well-being.  For  example,  we  regularly  conduct  internal  surveys  to
assess  the  well-being  and  needs  of  our  employees,  and  we  significantly  expanded  employee  assistance  and  mindfulness  programs  to  help  employees  and  their  families
manage anxiety, stress, sleep, and overall well-being. Additionally, we believe that our employees are at their best when they take the time to recharge. In order to encourage
our  employees  to  recharge  and  make  their  well-being  a  priority,  we  provide  company-wide  “ChargeUp  Days”—paid  time  off  that  is  in  addition  to  our  company-recognized
holidays.

Board of Directors Oversight

Our board of directors recognizes the critical importance of our team and the necessity to ensure a diverse, inclusive, and creative work environment that is centered around a
values-based culture. Our board of directors meets regularly with management to discuss issues impacting our team members and ways to support our workforce. Our focus on
culture  comes  from  our  board  of  directors  and  flows  throughout  our  Company.  In  evaluating  our  Chief  Executive  Officer  and  management  team,  emphasis  is  put  on  their
contributions to our overall culture.

Sales and Marketing

Our sales and marketing organizations work closely together to increase awareness, generate user demand, build a strong sales pipeline, and grow account relationships across
businesses of all sizes, from small businesses to Fortune 100 companies, to accelerate GSV and revenue growth.

Marketing

We have a holistic and integrated marketing strategy with the goal of attracting clients to our work marketplace and helping them select the right product offering based on their
business needs. This starts with building awareness of our brand and the key benefits of hiring remote talent over using traditional staffing models, including talent quality, speed
to hire, flexibility, and cost effectiveness, all built upon trusted relationships and providing talent and clients more control over their careers and businesses. We draw insights
and trends from our work marketplace and primary research studies to drive broad public relations coverage. We also help shape influential conversations around the future of
work and the immediate strategic opportunities provided by flexible talent solutions through major media outlets to further drive brand awareness and cement our position as a
thought leader.

Building upon our brand positioning, we address key client needs in all our marketing efforts and help point our clients to the right Upwork product based on those needs. We
also enjoy the benefits of high Net Promoter Scores, which we refer to as NPS, that generate significant word-of-mouth growth. While a majority of our new client registrations
come through direct and non-paid channels, we also increase our new client pipeline with a variety of digital, direct mail, and event marketing programs. We deploy email and
lifecycle marketing initiatives to retain, cross-sell, and upsell existing clients. We also engage in offline advertising, as well as TV and radio advertising campaigns.

We have also increased our focus on large enterprise organizations by adding account-based marketing programs that target clients to drive account growth. Once prospects
are identified, our enterprise sales team works to broaden adoption of our work marketplace into wider-scale deployments.

Enterprise Sales

Our enterprise sales team consists of business development representatives and other quota-carrying account executives who are focused on acquiring new clients with at least
250 employees. Specifically, our business development representatives are focused on generating qualified opportunities within our target account profile, which include both
inbound and self-service customer upgrades. These opportunities are delivered to account executives focused on selling our Upwork Enterprise offering. Additionally, our quota-
carrying  account  management  and  success  teams  help  new  and  existing  clients  scale  usage  of  our  work  marketplace  throughout  their  organizations.  We  achieve  this  by
executing  awareness  campaigns,  persona-based  workshops,  webinars,  and  account-based  marketing  campaigns  that  drive  additional  client  spend  through  our  work
marketplace. We believe this land-and-expand strategy helps clients ramp their usage of our work marketplace and drives more value, awareness, and adoption over time.

Our Technology

We  invest  substantial  resources  in  research  and  development  to  enhance  our  platform,  develop  new  products  and  features,  and  improve  our  infrastructure.  We  utilize  a  flexible
systems architecture to allow us to scale easily as our

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platform usage increases and to provide a consistent and robust user experience. We host our platform on Amazon Web Services, which we refer to as AWS. The core focus of our
technology is on:

Reliability

Our infrastructure is designed to provide high reliability and robust platform performance. There are four components to our reliability strategy:

1. Modern Distributed Infrastructure. We have engineered and implemented a modern, distributed core infrastructure design that provides for failures to occur at the

individual system level without disrupting service or impacting the user experience.

2. Services-Oriented  Architecture.  We  have  focused  on  building  a  services-oriented  architecture  that  is  designed  to  independently  scale,  or  failover,  as  needed,

leveraging the AWS platform. As a result, we believe we are more resilient to unexpected surges in traffic or to new code changes that we may introduce.

Isolation as a Design Philosophy. Leveraging the philosophy of domain-driven design, we have divided our platform into multiple sections to reduce the likelihood
that a failure in any one section would negatively impact other sections of our platform.

Intelligent  Monitoring  and  Automated  Remediation.  Our  platform  is  designed  to  continuously  monitor  its  own  health  and  act  appropriately  to  maintain  its  health,
particularly during our deployment of new code or in response to any single infrastructure or platform issue.

3.

4.

Security

Our  platform  is  designed  to  help  ensure  the  security  of  our  data  and  systems,  protect  our  users’  personal  information,  and  to  meet  the  rigorous  privacy  and  security
requirements of our enterprise clients. To that end, we have obtained the following security and privacy certifications: ISO 27001 and 27018, SOC 2 Type II certification, SOC 3
certification, PCI-DSS certification, and U.S.-EU and U.S.-Swiss Privacy Shield certifications. We are also TrustArc certified.

Our information security controls operate at multiple levels and are designed to detect, prevent, and mitigate cybersecurity threats that could impact the privacy and security of
our data and our users’ data. To operate at scale, we have automated several risk mitigation strategies. We have implemented comprehensive trust and safety processes to
help  prevent  and  detect  suspicious  behavior  on  our  platform.  Over  the  years  of  developing  our  work  marketplace,  we  have  developed  and  refined  specific  pattern-matching
algorithms to detect unusual behavior on our work marketplace.

Another component of our security strategy is to leverage third parties who provide value-added user verification services. Augmenting user identity verification through these
third-party services improves our ability to ensure users are accurately represented and minimize suspicious activity on our platform.

All access to our platform is encrypted using industry-standard transport layer security technology. When users enter sensitive information, such as tax identification numbers,
we encrypt the transmission of that information using secure socket layer technology. We also use HTTP strict transport security to add an additional layer of protection for our
users. For servers that store personally identifiable information, the data is encrypted. In order to make secure payments through our platform, we are Payment Card Industry
Data Security Standard certified, which means we have demonstrated compliance with the Payment Card Industry security standards required for businesses that complete
credit card or debit card transactions.

Our users may elect to further secure their account credentials through two-factor authentication that requires them to authenticate on a second device.

Machine Learning Predictive Capabilities

We leverage historical data to create a continuously improving experience for our users. Our platform contains a large repository of closed-loop data for the entire life cycle of
work, starting from when clients post projects to when talent and clients match, how they communicate, how and when payment is transferred, and feedback.

Utilizing machine learning capabilities to predict future behavior based on many years of historical use cases, we are able to leverage this data analysis to create stronger user
experiences.

During the search process, we leverage our proprietary data to help talent and clients efficiently connect. We leverage machine learning to balance supply and demand within
the platform as well. Talent receives data on

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market rates based on similar jobs when submitting proposals. When clients post jobs, similar rate resources also appear within the system. Upon registration, our machine
learning algorithms assess the potential of talent to be successful on our work marketplace.

Scalability

Our  cloud-based  platform  has  been  designed  to  be  elastic,  scaling  automatically  with  increased  usage,  supporting  sudden  traffic  spikes  by  dynamically  bringing  additional
capacity online as required, then scaling back to ensure consistent and predictable cost-management.

Our Impact

Our mission is to create economic opportunities so people have better lives. Everything we do to build a better way to work—from our offerings and services to the policies and
programs that guide our operations—is driven by this mission and our commitment to be a force for good.

Empowered by our work marketplace, millions of people from diverse backgrounds and locations can now access economic opportunities previously unavailable to them. We enable
workers to access opportunities beyond their local labor market and choose the type of projects they pursue, when and with whom they work, and how much they earn. Upwork
provides  a  new  way  for  talent  to  market  their  skills  and  expertise—one  based  on  merit—and  we  are  promoting  inclusive  hiring  practices  through  continuous  accessibility
improvements, analysis of potential underlying bias in our technology, and features like our certified-diverse badges.

We are also powering a more efficient and sustainable way to work. We believe that by facilitating remote work engagements and providing our users with the tools they need to
collaborate from afar, we are helping them avoid work-related commutes and business travel. By committing to carbon neutrality and pursuing ways to decrease our own footprint,
we are demonstrating how companies across the globe can take on climate change.

Our drive to create a more equitable and sustainable future of work has helped us identify new ways to serve our stakeholders—including our clients and the independent talent on
our work marketplace, our hybrid workforce, our investors, and our community partners—and contribute towards long-term value creation. We continuously assess our social and
environmental impact and we are committed to addressing both short- and long-term risks and opportunities across our supply chain, operations, and value chain. For this reason,
our  impact  strategy  is  focused  on  six  key  areas:  economic  opportunity;  business  integrity;  diversity,  inclusion,  and  belonging;  health,  safety,  and  human  rights;  environmental
sustainability; and supplier engagement.

Competition

The market segment for independent talent and the clients that engage them is highly competitive, rapidly evolving, fragmented, and subject to changing technology, shifting needs,
and  frequent  introductions  of  new  competitors  as  well  as  new  offerings  and  services.  The  level  of  competition  within,  and  the  frequency  and  likelihood  of  increased  third-party
investment and new competitors entering, this market segment has further intensified due to the ongoing COVID-19 pandemic and the resulting shift toward remote work and other
labor market dynamics. We compete with a number of online and offline platforms and services domestically and internationally, as well as traditional staffing firms, to attract and
retain users and expand our share of user spend.

We believe the principal competitive factors in our market segment include:

•

•

•

•

•

•

•

•

•

•

platform features and functionality, including efficient and accelerated time to hire;

verified talent work history and client payment history;

size and engagement of user base, including the ability to attract and retain clients with a need for independent talent services;

breadth of skill categories offered by a platform’s rated quality talent;

availability of high-quality projects from clients of all sizes, including Fortune 100 companies;

uniqueness, size, and scope of data assets;

ease of use;

brand awareness and reputation;

level of user satisfaction;

relationships with third-party partners;

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•

•

•

strength of sales and marketing efforts;

ability to innovate and develop new or improved offerings and services; and

pricing.

We believe that we compete favorably with respect to these factors.

Intellectual Property

The protection of our technology and intellectual property is an important aspect of our business. We rely upon a combination of patents, trademarks, trade secrets, copyrights,
confidentiality procedures, contractual commitments, and other legal rights to establish and protect our intellectual property. We generally enter into confidentiality agreements and
invention or work product assignment agreements with our employees, independent team members that we engage through our work marketplace, advisors, and consultants to
control access to, and clarify ownership of, our software and other inventions and intellectual property, documentation, and other proprietary information.

As of December 31, 2021, we held 22 issued U.S. patents. As of December 31, 2021, we held eight registered trademarks in the United States, including Upwork, Elance, oDesk,
and “Talent Cloud” and also held 161 registered trademarks in foreign jurisdictions. We continually review our development efforts to assess the existence and patentability of new
intellectual property.

Government Regulation

We have a robust regulatory compliance program built to comply with the various applicable U.S. federal and state and foreign laws and regulations that are applicable to internet
companies and businesses that operate online marketplaces connecting businesses with independent talent. Our compliance program gives us the ability to pursue products and
features  that  are  or  may  be  governed  by  complex  laws  and  regulatory  regimes.  These  laws  and  regulations  may  involve  areas  such  as  worker  classification,  employment,  data
protection, online payment services, content regulation, intellectual property, taxation, consumer protection, background checks, payment services, money transmitter regulations,
anti-corruption, anti-money laundering and sanctions laws, or other subjects. Moreover, we provide escrow services to our users and are therefore licensed as an internet escrow
agent by the DFPI. Many of the laws and regulations that are or may be applicable to our business are still evolving and being tested in courts and could be interpreted in ways that
could adversely impact our business. In addition, the application and interpretation of these laws and regulations often are uncertain, particularly in the industry in which we operate.
We continue to monitor existing and pending laws and regulations and while the impact of regulatory changes cannot be predicted with certainty, we do not expect compliance to
have a material adverse effect.

Corporate Information

We  were  incorporated  in  the  State  of  Delaware  in  December  2013  prior  to  and  in  connection  with  the  combination  of  Elance,  Inc.,  which  we  refer  to  as  Elance,  and  oDesk
Corporation, which we refer to as oDesk. In connection with the combination, we changed our name to Elance-oDesk, Inc. in March 2014, and then to Upwork Inc. in May 2015. In
2015, we commenced consolidation of the Elance platform and the oDesk platform and following the consolidation in 2016, began operating under a single work marketplace.

Our  principal  executive  office  is  located  at  475  Brannan  Street,  Suite  430,  San  Francisco,  California  94107,  and  our  mailing  address  is  655  Montgomery  Street,  Suite  490,
Department 17022, San Francisco, California 94111. Our telephone number is (650) 316-7500. Our website address is www.upwork.com. The information contained on, or that can
be accessed through, our website is not a part of this Annual Report. Investors should not rely on any such information in deciding whether to purchase our common stock. Unless
otherwise  expressly  stated  or  the  context  otherwise  requires,  references  in  this  Annual  Report  to  “Upwork,”  the  “Company,”  “our,”  “us,”  and  “we”  and  similar  references  refer  to
Upwork Inc. and its wholly-owned subsidiaries.

Upwork, the Upwork logo, Upwork Enterprise, Elance, oDesk, “Talent Cloud,” and other registered or common law trade names, trademarks, or service marks of Upwork appearing
in this Annual Report are the property of Upwork. This Annual Report contains additional trade names, trademarks, and service marks of ours and of other companies. We do not
intend our use or display of other companies’ trade names, trademarks, or service marks to imply a relationship with these other companies, or endorsement or sponsorship of us
by these other companies. Other trademarks appearing in this Annual Report are the property of their respective holders. Solely for convenience, our trademarks and trade names
referred to in this Annual Report appear without the ® and ™ symbols, but those references are not intended to indicate, in any way, that we will not assert, to the fullest extent
under applicable law, our rights, or the right of the applicable licensor, to these trademarks and trade names.

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Available Information

We file annual reports on Form 10-K, quarterly reports on Form 10-Q, current reports on Form 8-K, and amendments to reports filed or furnished pursuant to Sections 13(a) and
15(d) of the Exchange Act with the SEC. The SEC maintains a website at www.sec.gov that contains reports, proxy and information statements and other information that we file
with the SEC electronically. Copies of our reports on Form 10-K, Forms 10-Q, and Forms 8-K, and amendments to those reports may also be obtained, free of charge, electronically
through our investor relations website located at the web address appearing below as soon as reasonably practicable after we file such material with, or furnish it to, the SEC.

We  use  our  investor  relations  website  (investors.upwork.com),  our  Twitter  handle  (twitter.com/Upwork),  and  Hayden  Brown’s  Twitter  handle  (twitter.com/hydnbrwn)  and  LinkedIn
profile  (linkedin.com/in/haydenlbrown)  as  a  means  of  disseminating  or  providing  notification  of,  among  other  things,  news  or  announcements  regarding  our  business  or  financial
performance, investor events, press releases, and earnings releases and as a means of disclosing material non-public information and for complying with our disclosure obligations
under  Regulation  FD.  The  content  of  our  websites  and  information  that  we  may  post  on  or  provide  to  online  and  social  media  channels,  including  those  mentioned  above,  and
information that can be accessed through our websites or these online and social media channels are not incorporated by reference into this Annual Report or in any other report or
document we file with the SEC, and any references to our websites or these online and social media channels are intended to be inactive textual references only.

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Item 1A. Risk Factors.

A description of the risks and uncertainties associated with our business is set forth below. You should carefully consider the risks and uncertainties described below, as well as the
other information in this Annual Report, including our consolidated financial statements and the related notes and “Management’s Discussion and Analysis of Financial Condition
and Results of Operations.” The occurrence of any of the events or developments described below, or of additional risks and uncertainties not presently known to us or that we
currently deem immaterial, could materially and adversely affect our business, results of operations, financial condition, and growth prospects. In such an event, the market price of
our common stock could decline and you could lose all or part of your investment.

Summary of Risk Factors

Some of the more material risks that we face include:

• Our growth depends on our ability to attract and retain a community of talent and clients, and the failure to maintain or grow our community of users could adversely impact

our business.

•

If  we  fail  to  maintain  or  increase  activity  by  existing  users  in  a  cost-effective  manner  or  at  all,  our  revenue  will  grow  more  slowly  than  expected  or  may  decline  and  our
business will be adversely impacted.

• We have experienced growth in recent periods and expect to continue to invest in our growth for the foreseeable future. If we are unable to maintain similar levels of growth

or manage our growth effectively, our business, revenue and profits, and financial condition could be adversely affected.

• Our  business  experienced,  and  may  again  experience,  an  adverse  impact  from  the  ongoing  COVID-19  pandemic,  including  as  new  variants  of  COVID-19  emerge.  In
addition, the positive impacts on our business resulting from the shift to remote work during the pandemic may not continue as the pandemic subsides and the restrictions
intended to prevent its spread are relaxed or lifted.

• We  have  a  limited  operating  history  under  our  current  business  strategy  and  pricing  model,  and  will  continue  to  evolve  our  business  strategy  and  pricing  model,  which

makes it difficult to evaluate our business and future prospects.

• Changes to our offerings and pricing model have in the past adversely affected, and could in the future adversely affect, our business.

• We face payment and fraud risks that could adversely impact our business.

•

If we are unable to maintain our payment partner relationships on favorable terms, or at all, our business could be adversely affected.

• Our revenue growth and ability to achieve and sustain profitability will depend in part on being able to increase the productivity, effectiveness, and efficiency of our sales

force.

•

Because we derive the substantial majority of our revenue from our marketplace offerings, our inability to generate revenue from our marketplace offerings would adversely
affect our business operations, financial results, and growth prospects.

• We face intense competition and could lose market share to our competitors, including if we fail to continue to develop and enhance our existing offerings and services,

which could adversely affect our business, operating results, and financial condition.

•

•

•

•

If we fail to develop, maintain, and enhance our brand and reputation cost-effectively, our business and financial condition may be adversely affected.

If  the  market  for  independent  talent  and  the  services  they  offer  develops  more  slowly  than  we  expect,  our  growth  may  slow  or  stall,  and  our  operating  results  could  be
adversely affected.

Because a substantial portion of the services offered by talent and sought by clients on our work marketplace is information technology services, a decline in talent offering
information technology services or the market for information technology service providers on our work marketplace could adversely affect our business.

Errors, defects, or disruptions in our work marketplace, including any security breach, other hacking or phishing attack, or other privacy or security incident, could diminish
demand, adversely impact our financial results, and subject us to liability.

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• Our sales efforts are increasingly primarily targeted at large enterprise and other clients and prospects with larger, longer-term independent talent needs, and as a result we
may encounter greater pricing, implementation, and customization challenges, and we may incur additional costs, each of which could adversely impact our business and
operating results.

• Users circumvent our work marketplace, which adversely impacts our business.

• We and our users may be subject to new and existing laws and regulations, both in the United States and internationally.

• Having an international community of users and engaging talent internationally exposes us to risks that could have an adverse effect on our business, operating results, and

financial condition, and these risks could increase as we seek to expand our international footprint.

•

•

There may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is challenged, and
our business could be adversely affected by changes in laws regarding contractor classification.

The  success  of  our  business  relies  on  demand  for  talent  and  any  change  that  affects  demand  for  talent,  including  regulatory  or  tax  changes,  or  adverse  perception
regarding use of talent, would adversely affect our business.

• We have a history of net losses, anticipate increasing our operating expenses in the future, and may not achieve or sustain profitability.

• Our operating results may fluctuate from quarter to quarter, which makes our future results difficult to predict.

•

The stock price of our common stock has been and may continue to be volatile, and you could lose all or part of your investment.

• Our indebtedness could limit the cash flow available for our operations and expose us to risks that could adversely affect our business, financial condition, and results of

operations.

•

Adverse or changing economic and political conditions may negatively impact our business.

• We may be adversely affected by natural disasters and other catastrophic events, including the ongoing COVID-19 pandemic, by man-made problems such as terrorism, or
failures  of  technology,  that  could  disrupt  our  business  operations  and  our  business  continuity  and  disaster  recovery  plans  may  not  adequately  protect  us  from  a  serious
disaster.

Risks Related to our Business Operations, Execution, and Growth

Our growth depends on our ability to attract and retain a community of talent and clients, and the failure to maintain or grow our community of users could adversely
impact our business.

The size of our community of users, including both talent and clients, is critical to our success. Our ability to achieve significant growth in revenue in the future will depend, in large
part,  upon  our  ability  to  attract  new  users,  including  large  enterprise  and  other  clients  with  larger,  longer-term  independent  talent  needs,  as  well  as  talent  that  meet  the  criteria
sought by such clients, to, and retain existing users on, our work marketplace.

Talent have many different ways of marketing their services, securing clients, and obtaining payments from clients, including advertising to, and engaging with, prospective clients
through other online or offline platforms and methods, signing up for online or offline third-party agencies and staffing firms, using other payment services, or finding employment
directly  with  a  business.  Likewise,  there  may  be  impediments  to  talent  who  would  like  to  use  our  work  marketplace,  including  geopolitical  events,  military  conflicts,  sanctions
regimes, the talent’s inability to access technology or internet, or other external causes, and these events in areas where certain talent resides, such as Russia or Ukraine, could
impact our business. If we fail to attract new talent; the quality or types of services provided by talent on our work marketplace are not satisfactory to clients; talent are not located in
geographic regions in which clients are seeking to engage remote talent; talent decrease their use of, or cease using, our work marketplace or prefer to take remote employment
opportunities or to use other online remote work platforms, both of which are increasingly available as a result of the shift to remote work, clients may decrease their use of, or
cease using, our work marketplace and our revenue may be adversely impacted.

Clients have similarly diverse options to find and engage service providers, such as finding service providers through other online or offline platforms or through staffing firms and
agencies, engaging service providers directly,

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using other talent sourcing services, or hiring temporary, full-time, or part-time employees directly or through an agency.

Beginning in the second half of 2019, we began evolving our offerings, services, brand positioning, and marketing to better address large enterprise and mid-market prospects and
other clients with larger, longer-term independent talent needs. And more recently, we have prioritized our advertising, marketing, and product development efforts to reach those
new and existing clients seeking to engage remote talent in light of the acceleration in the shift toward remote work, due in part to the COVID-19 pandemic. To further achieve our
goals, we expect to increasingly engage in sophisticated, costly, and lengthy sales and marketing and internationalization or localization efforts that may not result in additional users
that transact on our work marketplace or effectively retain our current users that transact on our work marketplace, or may not do so in a cost-effective manner. The evolution of
these and other efforts, either individually or in the aggregate, may not be successful in attracting and retaining users or growing client spend from these target clients, and in the
event these efforts result in the loss of or reduction in spend by other clients that is not offset by increased activity from these target clients, they may result in a temporary or long-
term deceleration in GSV growth. In addition, any increase in user acquisition resulting from the COVID-19 pandemic may slow or decline as the impact of the COVID-19 pandemic
subsides. For example, growth in the number of active clients decelerated on a year-over-year basis in the third and fourth quarters of 2021. See “—Active Clients and GSV per
Active Client” below for the definition of active client.

We may also modify our pricing model, or introduce new, modify, or consolidate existing offerings or other services and features to attract and retain users. Such actions may not
have the intended effect of attracting and retaining users at the levels we anticipated and may have unintended negative consequences, such as a loss of users or a reduction of
user activity or spend on our work marketplace.

If we fail to maintain or increase activity by existing users in a cost-effective manner or at all, our revenue will grow more slowly than expected or may decline and our
business will be adversely impacted.

Users can generally decide to cease using our work marketplace and related services at any time. Users may stop using our work marketplace and related services if the quality of
the user experience on our work marketplace, including our support capabilities, does not meet their expectations or keep pace with the quality of the user experience generally
offered by competitive products and services. Users may also choose, and in the past have chosen, to cease using our work marketplace if they perceive that our pricing model,
including associated fees, is not in line with the value they derive from our work marketplace, or for other reasons, including cost-cutting measures. Moreover, as discussed below in
the risk factor titled “Users circumvent our work marketplace, which adversely impacts our business,” users circumvent the payment services on our work marketplace and talent
receive payment directly or through another service, which is likely to happen more frequently during a macroeconomic downturn, as users may be more cost sensitive during such
period. In addition, expenditures by clients may be cyclical and may reflect overall macroeconomic conditions or budgeting patterns.

Additionally, one client accounted for more than 10% of our trade and client receivables as of December 31, 2021 and three clients each accounted for more than 10% of our trade
and client receivables as of December 31, 2020. Although for the years ended December 31, 2021 and December 31, 2020, we did not have any clients that accounted for more
than 10% of our revenue, a decrease in spend from any of our larger clients, or failure of our larger clients to pay us, could have an adverse effect on our operating results.

Any decrease in the attractiveness of our work marketplace, failure to retain users, or reduced spending by clients could lead to decreased activity, diminished network effects, or a
drop  in  GSV  on  our  work  marketplace,  which  could  adversely  affect  our  business,  revenue,  financial  condition,  and  operating  results.  We  expect  our  GSV  to  fluctuate  between
periods due to a number of factors, including the number of active clients on our work marketplace, seasonality in the labor market, the volume and characteristics of projects that
are posted by clients on our work marketplace, such as size, duration, pricing, and the availability and qualification of talent to complete client projects, and other factors.

If users stop using, or reduce their use of, our work marketplace and related services for any reason, including the foregoing reasons, our revenue and business would be adversely
affected.

We have experienced growth in recent periods and expect to continue to invest in our growth for the foreseeable future. If we are unable to maintain similar levels of
growth or manage our growth effectively, our business, revenue and profits, and financial condition could be adversely affected.

We have experienced growth in a relatively short period of time. For example, our total revenue for the year ended December 31, 2021 was $502.8 million, representing a period-
over-period growth rate of 35% over the same period in 2020. This revenue growth was due in part to the shift toward remote work resulting from the COVID-19

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pandemic and therefore may not be indicative of future growth. For example, future period-over-period revenue growth rates, when compared against the quarterly and full-year
results of 2021, may fail to meet the expectations of investors or securities analysts given the accelerated revenue growth experienced during such periods due to the COVID-19
pandemic and the resulting increased adoption of remote work and reduced seasonality experienced during such periods. Moreover, typical seasonality in the labor market may be
exaggerated (for example, extended vacations during the summer and holiday seasons) as the COVID-19 pandemic subsides and the restrictions intended to prevent its spread are
relaxed or lifted, which may further impact period-over-period revenue growth rates. Sustaining our growth will place significant demands on our management as well as on our
administrative,  operational,  and  financial  resources.  To  manage  our  growth,  we  must  continue  to  improve  our  operational,  financial,  and  management  information  systems  and
processes; expand, motivate, retain, and effectively manage and train our workforce; and effectively collaborate with our third-party partners, all of which can be more difficult with
an  increasingly  remote  workforce  and  an  increasingly  competitive  labor  market.  If  we  are  unable  to  manage  our  growth  successfully  without  compromising  the  quality  of  our
offerings or user experience, or if new systems that we implement to assist in managing our growth do not produce the expected benefits, our business, operating results, financial
condition, and ability to successfully market our work marketplace and serve our users could be adversely affected.

Our  recent  and  historical  growth  should  not  be  considered  indicative  of  our  future  performance.  We  have  encountered,  and  will  encounter  in  the  future,  risks,  challenges,  and
uncertainties,  including  those  frequently  experienced  by  growing  companies  in  rapidly  changing  and  highly  competitive  industries.  If  our  assumptions  regarding  these  risks,
challenges, and uncertainties, which we use to plan and operate our business, are incorrect or change, or if we do not address these risks successfully, our financial condition and
operating  results  could  differ  materially  from  our  expectations  and  those  of  investors  and  securities  analysts,  our  growth  rates  may  slow,  and  our  business  would  be  adversely
impacted.

Our  business  experienced,  and  may  again  experience,  an  adverse  impact  from  the  ongoing  COVID-19  pandemic,  including  as  new  variants  of  COVID-19  emerge.  In
addition,  the  positive  impacts  on  our  business  resulting  from  the  shift  to  remote  work  during  the  pandemic  may  not  continue  as  the  pandemic  subsides  and  the
restrictions intended to prevent its spread are relaxed or lifted.

The COVID-19 pandemic adversely impacted our business for a period of time and resulted in reductions in demand for our offerings and services by some of our clients, including
small- and medium-sized business clients, which have been the most impacted by the resulting macroeconomic downturn and uncertainty and from which we derive a substantial
portion of our GSV and revenue. Conversely, beginning in 2020 we experienced an increase in GSV and revenue growth driven by an acceleration in the shift toward remote work,
due in part to the COVID-19 pandemic. These positive impacts may not continue as the pandemic subsides and the restrictions intended to prevent its spread are relaxed or lifted,
which may negatively impact our GSV and revenue growth.

The extent to which the ongoing COVID-19 pandemic will adversely affect our business, financial condition, results of operations, and cash flow will depend on future developments,
which  are  highly  uncertain  and  cannot  reasonably  be  predicted  with  confidence  at  this  time,  including  the  duration,  spread,  and  severity  of  the  outbreak,  or  the  occurrence  of
additional  “waves”  of  the  outbreak;  the  emergence  of  variant  strains  of  the  virus;  the  availability,  utilization,  and  efficacy  rates  of  vaccinations;  government  responses  to  the
pandemic and potential restrictions on our business and the businesses of our users; the impact of the pandemic on the U.S. and global economies and demand for our offerings;
how  quickly  and  to  what  extent  normal  economic  and  operating  conditions  resume;  and  the  reaction  of  users  and  potential  users  to  these  developments,  among  others.  The
potential impacts of such developments include, but are not limited to:

•

•

•

•

•

decline or reduction in demand on our work marketplace, resulting in lower GSV and revenue growth, during and following relaxation or lifting of restrictions intended to
prevent the spread of COVID-19, including the impact of resulting exaggerated seasonality;

reduced client spend on our offerings and services;

diminished ability to acquire new clients, particularly large enterprise and other clients with larger, longer-term independent talent needs;

increased competition as new competitors enter our market segment due to the accelerated shift toward remote work;

increased costs as a result of marketing and promotional efforts;

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•

•

•

•

•

•

•

•

•

•

•

•

•

•

•

•

•

increased risk of data breach or cybersecurity incidents as a result of additional workers accessing corporate systems remotely;

increased risk of fraud, cybersecurity attacks, or other illegal activity conducted by bad actors seeking to take advantage of our users or us due to the uncertainty around the
COVID-19 pandemic;

increased  employee  and  contractor  attrition  and  reduced  availability  of  key  personnel  to  conduct  important  business  activities,  such  as  providing  support  to  users  and
developing new offerings or services;

reduced ability to retain, attract, train, and integrate highly skilled personnel;

any impairment charges on our operating lease asset and related leasehold improvements being recognized as a general and administrative expense due to a reduction to
our office space and our potential sublease of such office space at a rental rate that is less than our rent expense for such office space, or any termination fees we may
incur as a result of our termination of the operating lease for such office space. For example, as a result of our shift to a flexible work model for our workforce, in 2021 we
subleased the entirety of our former headquarters in Santa Clara, California and a portion of our current headquarters in San Francisco, California, and, as a result, we
incurred impairment charges of $8.7 million;

reduced spend by clients or availability of talent located in areas or regions more affected by the COVID-19 pandemic;

reduced GSV and revenue as a result of increased user circumvention of our work marketplace;

reduced GSV and revenue as a result of talent reducing the fees they charge to clients due to an excess number of talent joining our work marketplace;

difficulty in business planning and forecasting due to significant uncertainty in the impact of the COVID-19 pandemic on all aspects of our business and on our clients, talent,
and other business partners;

longer sales cycles due to slower decision-making, reduced budgets, or delays in planned work by existing and potential clients;

impacts  on  payment  partners,  disbursement  partners,  or  other  critical  third-party  partners  that  may  cause  delays  in  processing  payments  to  talent  or  other  important
functions  of  our  work  marketplace,  result  in  an  increase  in  payment  transaction  costs,  lead  to  loss  of  revenue,  or  cause  a  decline  in  quality  or  availability  of  services,
negatively affect our reputation or user activity on our work marketplace, or increase our operating costs;

delayed or missed client payments to us or talent, which may also result in reductions in revenue, increased transaction losses, numbers of disputes with users, and costs
as we seek to compel payment, which we may not be able to recover;

significant disruption of global financial markets, which may impact our ability to access capital now or in the future or make capital available only on terms less favorable to
us;

reduced sublease income as a result of our sublease tenants being unable or unwilling to make the rental payments set forth in their respective sublease agreement;

impairments to our goodwill or other long-term assets if their carrying value exceeds their fair value;

increased  obligations  to  satisfy  our  escrow  funding  requirements  with  our  own  funds  or  by  drawing  on  our  line  of  credit  as  a  result  of  more  frequent  declines  of  client
payment methods or increased client-issued chargebacks, which would negatively impact our cash flows and may result in higher credit card processing fees; and

de-globalization, which may result in clients being less willing to connect with non-U.S. users of our work marketplace.

Although  the  COVID-19  pandemic  did  not  have  a  material  adverse  impact  on  our  financial  results  for  the  year  ended  December  31,  2021,  the  rapidly  changing  market  and
macroeconomic conditions caused by the COVID-19 pandemic have impacted the business of many of our clients, which resulted in a reduction in spend on our work marketplace
for some of those affected clients. There can be no assurance that the positive impacts from the COVID-19 pandemic, such as increased talent and client acquisitions, increased
client spend, and increased client retention, will continue to offset those parts of our business that have been adversely impacted. Many of these risk factors are unpredictable and
outside of our control, and any of these factors could amplify the other risks and uncertainties described elsewhere in this Annual Report. It is uncertain what impact that the various
legislative and

15

other government responses being undertaken in the United States and other countries, including with respect to the approval and distribution of vaccines, in which our users are
located will have on the economy, our industry, our partners, our users, and our company. In connection with the COVID-19 pandemic, we have also implemented measures to
protect the health of our workforce, including by adopting a flexible work model for our workforce that we believe will result in most of our employees working remotely even after the
pandemic is over. These measures may negatively impact the health and safety of our employees, impact workforce productivity, increase the risk of data security breaches and
other privacy and security incidents, and may cause other disruptions to our business. As and to the extent offices reopen, our efforts to comply with applicable health guidelines
may not prove sufficient to protect the health of our employees and other visitors to our offices, and our adoption of these measures may adversely affect our business operations.
Even after the COVID-19 pandemic has subsided, we may continue to experience adverse impacts to our business. For example, any increase in client acquisition due to the shift
toward remote work as a result of the COVID-19 pandemic may slow or decline as the impact of the COVID-19 pandemic subsides and users are no longer subject to restrictions
intended to prevent the spread of COVID-19.

We have a limited operating history under our current business strategy and pricing model, and will continue to evolve our business strategy and pricing model, which
makes it difficult to evaluate our business and future prospects.

We recently evolved, and will continue to evolve, our sales, marketing, and brand positioning efforts, as well as our business strategy. Recently, we have undertaken a rebranding
effort and expanded our focus on large enterprise and other clients and prospects with larger, longer-term independent talent needs. In an effort to better serve this market segment,
we recently expanded our Upwork Enterprise offering, which is designed to help large enterprise businesses connect with talent and provide clients with additional offerings and
services. We continue to evaluate and revise our current offerings and pricing model and create and test additional offerings, pricing models, features, and services to serve these
and other market segments. We regularly launch new offerings such as “Project Catalog,” a feature through which talent can market pre-scoped projects that are easily purchased
via a click-and-buy experience. Creating new offerings is expensive and time consuming, diverts the attention of our management, and not all offerings achieve market acceptance
at the levels we expect and therefore may not be cost-effective to maintain. For example, in 2019, we launched our Upwork Business offering, focused on mid-market businesses. In
the fourth quarter of 2020, we decided that it was no longer cost-effective for our sales team to sell our Upwork Business offering. This decision resulted in a reduction in force of
approximately one-third of our sales employees in the fourth quarter of 2020. Moreover, if an offering does not achieve sufficient market acceptance or otherwise does not achieve
its intended effect, we may expend additional resources and divert the attention of management to implement modifications in an effort to improve the offering, and these efforts may
not be successful.

Changes in our offerings and pricing, and the continued evolution of our business strategy, subject us to a number of uncertainties, including our ability to plan for and model future
growth  and  make  accurate  projections  regarding  our  future  performance.  In  addition,  we  have  in  the  past  seen,  and  may  in  the  future  see,  unexpected  or  unintended  negative
effects, as a result of changes to our pricing model, offerings, and sales, brand positioning, and marketing efforts, including a failure to attract and retain quality talent or attract new
clients that spend on our work marketplace or the loss of spend from existing clients. We cannot ensure that we will be successful in addressing these and other challenges we may
face in the future, and our business may be adversely affected if we do not manage these challenges successfully.

Changes to our offerings and pricing model have in the past adversely affected, and could in the future adversely affect, our business.

From time to time we have made, and will continue to make, changes to our offerings and pricing model, including in 2019 when we launched new paid membership types for clients
and new Connects pricing for talent, which resulted in user dissatisfaction and negatively impacted fill rates for projects on our work marketplace. From time to time, we will make
further changes to our offerings and pricing model, including with respect to Connects, due to a variety of reasons, including changes to the market for our offerings and services or
our business strategy, as new competitors enter our market segment, as we introduce, refine, or consolidate our offerings, as competitors introduce new products and services, and
to  grow  our  user  base.  Changes  to  any  components  of  our  pricing  model  have  in  the  past,  and  may  in  the  future,  among  other  things,  result  in  user  dissatisfaction,  increased
circumvention, lead to a loss of GSV, revenue, or users, result in a change to the way we recognize revenue, reduce the amount of revenue we generate as a percentage of GSV,
affect the taxability of our services and increase our tax exposure, reduce the rate or size of projects that get posted or completed on our work marketplace, negatively impact fill
rates for projects on our work marketplace, or otherwise negatively impact our reputation, operating results, financial condition, and cash flows.

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We face payment and fraud risks that could adversely impact our business.

Our work marketplace systems and controls relating to customer identity verification, user authentication, and fraud detection are complex. If such systems and controls are not
effective, our work marketplace may be perceived as not being secure, our reputation may be harmed, we may face regulatory action, and our business may be adversely impacted.
In addition, bad actors around the world use increasingly sophisticated methods to engage in illegal activities involving personal information, such as unauthorized or fraudulent use
of  another’s  identity,  payment  information,  or  other  information;  misrepresentation  of  the  user’s  identity,  location,  or  skills,  including  using  accounts  that  they  have  purchased,
borrowed,  or  leased;  and  the  improper  acquisition  or  use  of  credit  or  debit  card  details  and  banking  or  other  payment  account  information.  These  types  of  illegal  activities  may
increase as platforms like ours gain more prominence, including due to the ongoing shift toward remote work or in the event of a macroeconomic downturn, and as we become
more visible as a result of our brand promotion efforts, as bad actors seek to take increasing advantage of us or our users. This conduct on our website could result in any of the
following, each of which could adversely impact our business:

•

bad  actors  may  use  our  work  marketplace,  including  our  payment  processing  and  disbursement  methods,  to  engage  in  unlawful  or  fraudulent  conduct,  such  as  money
laundering,  moving  funds  to  regions  or  persons  restricted  by  sanctions  or  export  controls,  terrorist  financing,  fraudulent  sale  of  services,  bribery,  breaches  of  security,
unauthorized  acquisition  of  data,  extortion  or  use  of  ransomware,  distribution  or  creation  of  malware  or  viruses,  piracy  or  misuse  of  software  and  other  copyrighted  or
trademarked content, and other misconduct;

• we may be, and historically have been, held liable for the unauthorized use of credit or debit card details and banking or other payment account information and required by
card issuers, banks, and other payment partners to return the funds at issue and pay a chargeback or return fee, and if our chargeback or return rate becomes excessive,
credit card networks may also require us to pay fines or other fees or cease doing business with us and the California Department of Financial Protection and Innovation,
which we refer to as the DFPI, may require us to hold larger cash reserves or take other action with respect to our internet escrow license;

• we may be subject to additional risk and liability exposure, including for negligence, fraud, or other claims, if employees or third-party service providers, including talent that
provide services to us, misappropriate our banking, payment, or other information or user information for their own gain or to facilitate the fraudulent use of such information;

•

users that are subjected or exposed to the unlawful, fraudulent, or improper conduct of other users or other third parties may seek to hold us responsible for the conduct of
or content posted by users, may lose confidence in our work marketplace, decrease or cease use of our work marketplace, seek to obtain damages and costs, or publicize
their negative experiences, and law enforcement or administrative agencies could seek to hold us responsible for the conduct of or content posted by users, impose fines
and penalties, bring criminal action, or require us to change our business practices, and private or public enforcement may increase depending on interpretations of and
possible changes to intermediary liability provisions such as Section 230 of the Communications Decency Act of 1996;

• we  may  be  subject  to  additional  risk  if  clients  fail  to  pay  talent  for  services  rendered,  as  talent  may  seek  to  hold  us  responsible  for  the  clients’  conduct  and  may  lose
confidence in our work marketplace, may decrease or cease use of our work marketplace, may publicize their negative experiences, or seek to obtain damages and costs;

•

if  talent  misstate  their  qualifications  or  location,  provide  misinformation  about  their  skills,  identity,  or  otherwise,  perform  services  they  are  not  qualified  or  authorized  to
provide, produce insufficient or defective work product or work product with a viral or other harmful effect, clients or other third parties may seek to hold us responsible for
the talents’ acts or omissions and may lose confidence in our work marketplace, decrease or cease use of our work marketplace, or seek to obtain damages and costs; and

• we may suffer reputational damage adversely impacting our business as a result of the occurrence of any of the above.

We do not have control over users of our work marketplace and cannot ensure that any measures we have taken to detect, prevent, and mitigate these risks will stop or minimize
the use of our work marketplace for, or to further, illegal or improper purposes. We have received in the past, and are likely to continue to receive in the future, complaints and
inquiries from clients, talent, and other third parties, including law enforcement, administrative agencies, and the press, concerning misuse of our work marketplace and wrongful
conduct of other users. We have

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also brought claims against clients and other third parties for their misuse of our work marketplace, and may be required to bring similar claims in the future. Even if these claims do
not result in litigation or are resolved in our favor, these claims, and the time and resources necessary to resolve them, could divert the attention and resources of our management,
negatively impact our reputation, and adversely affect our business and operating results.

If we are unable to maintain our payment partner relationships on favorable terms, or at all, our business could be adversely affected.

Our payment partners consist of payment processors and disbursement partners. We rely on banks and payment partners to provide us with corporate banking services, escrow
trust accounts, and clearing, processing, and settlement functions for the funding of all transactions on our work marketplace, and disbursement of funds to users, and we do not
always have a sufficient surplus of vendors in the event one or more relationships is terminated for any reason.

Our payment partners are critical to our business. In order to maintain these relationships, we have in the past been, and may in the future be, forced to agree to terms that are
unfavorable to us. If we are unable to maintain our agreements with current payment partners on favorable terms, or at all, or we are unable to enter into new agreements with new
payment partners on favorable terms, or at all, our ability to collect payments and disburse funds and our revenue and business may be adversely affected. This could occur for a
number of reasons, including the following with respect to our payment partners:

•

our partners may be unable or unwilling to perform the services we require of them, such as processing payments to talent in a timely manner, including in a manner that is
satisfactory to us as it relates to compliance with U.S. federal, state, and international laws and regulatory requirements;

• we  may  choose  to  cease  doing  business  with  our  partners  for  a  number  of  reasons,  including  as  a  result  of  their  failure  to  comply  with  applicable  payment  or  banking

regulations or due to allegations of fraud or other impropriety by them or their third-party partners;

•

•

•

•

•

•

our  partners  may  be  subject  to  investigation,  regulatory  enforcement,  or  other  proceedings  that  result  in  their  inability  or  unwillingness  to  provide  services  to  us  or  our
unwillingness to continue to partner with them;

our partners may be unable to effectively accommodate changing service needs, such as those which could result from rapid growth or higher volume or those which relate
to international expansion and local jurisdictions;

our partners could, and, in some cases, have notified us in the past that they would, increase the rates that they charge us or our users, especially in light of changes in
those partners’ interpretation and enforcement of their rules, increased declines of client payment methods, or increased client-issued chargebacks;

our partners could choose to terminate or not renew their agreements with us, or only be willing to renew on different or less advantageous terms;

our partners could reduce the services provided to us, cease doing business with us, or cease doing business altogether;

our partners could be subject to delays, limitations, or closures of their own businesses, networks, partners, or systems, causing them to be unable to process payments or
disburse funds for certain periods of time; or

• we  may  be  forced  to  cease  doing  business  with  certain  partners  if  card  association  operating  rules,  certification  requirements  and  laws,  regulations,  or  rules  governing

electronic funds transfers to which we are subject, change or are interpreted to make it difficult or impossible for us to comply.

For example, in June 2020, Wirecard AG, a prepaid card issuer used by one of our payment partners to issue prepaid cards to our non-U.S. users, filed for insolvency and was
ordered by the UK Financial Conduct Authority to cease all licensed activity. As a result, our non-U.S. users who previously chose to withdraw their funds to a prepaid card could not
access their funds for several days. The order was eventually lifted, allowing those users to access their funds; however, this incident or any similar future incident concerning our
payment partners or their respective vendors could cause our users to lose trust in our work marketplace and could have an adverse impact on our business.

Our revenue growth and ability to achieve and sustain profitability will depend in part on being able to increase the productivity, effectiveness, and efficiency of our
sales force.

In order to increase our revenue from our premium offerings and achieve and sustain profitability, we must improve the effectiveness and efficiency of our sales force and generate
additional revenue from new and existing users. For

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example,  in  the  fourth  quarter  of  2020,  we  completed  an  evaluation  of  the  efficiency,  productivity,  and  effectiveness  of  our  sales  force  at  generating  revenue  from  our  Upwork
Business offering, as well as our other premium offerings. As part of this evaluation, we undertook a reduction in force of approximately one-third of our sales employees in an effort
to drive efficiencies in our sales organization. Moreover, in the fourth quarter of 2021, we began increasing our investment in sales by expanding our sales team and we expect this
expansion to continue through 2022 as we increase our efforts to acquire clients for our Upwork Enterprise offering.

There  is  significant  competition  for  sales  personnel  with  the  skills  and  technical  knowledge  required  to  maintain  a  productive  and  efficient  sales  force.  Our  ability  to  achieve
significant  revenue  growth  will  depend,  in  large  part,  on  our  success  in  recruiting,  training,  effectively  deploying,  and  retaining  sufficient  numbers  of  sales  and  sales  support
personnel to support our growth. It is difficult to find, and we may be unable to retain, a sufficient number of sales personnel with the specific skills and technical knowledge needed
to sell our Upwork Enterprise and other premium offerings, particularly in light of the current global labor shortage. Furthermore, hiring and effectively deploying sales personnel,
particularly  in  new  markets,  is  complex  and  requires  additional  costs  that  we  may  not  recover  if  the  sales  personnel  fail  to  achieve  full  productivity.  Even  if  we  are  able  to  hire
qualified sales personnel, doing so may be costly and lengthy, as new sales personnel require significant training and can take a number of months to achieve full productivity. In
addition, new sales personnel do not always achieve productivity milestones within the timelines that we have projected, negatively impacting our ability to achieve our long-term
financial projections associated with such personnel. Not all of our sales personnel and planned hires have or will become productive, or do so as quickly as we expect. When our
new sales personnel do not become fully productive on the timelines that we have projected, or at all, our revenue will not increase at anticipated rates, or at all, and our ability to
achieve long-term projections may be negatively impacted. The COVID-19 pandemic and restrictions intended to prevent its spread adversely affected the productivity of our sales
force for a period of time, and may adversely affect it again as the COVID-19 pandemic subsides, as the productivity of our sales force may diminish as users return more frequently
to  physical  offices  or  are  otherwise  no  longer  subject  to  restrictions  related  to  the  COVID-19  pandemic.  If  our  sales  personnel  are  not  successful  in  obtaining  new  business  or
increasing sales to our existing user base, our business and results of operations will be adversely affected.

Our revenue growth depends in part on the success of our strategic relationships with third parties and their continued performance.

To  grow  our  business,  we  need  to  continue  to  establish  and  maintain  relationships  with  third  parties,  such  as  staffing  providers,  banks,  software  and  technology  vendors,  and
payment  processing  and  disbursement  providers.  For  example,  we  work  with  third-party  staffing  providers,  upon  which  we  are  dependent  to  support  our  employment  offering,
Upwork Payroll. As our agreements with third-party partners terminate or expire, we may be unable to renew or replace these agreements on favorable terms, or at all. Moreover,
we cannot guarantee that the parties with which we have strategic relationships will continue to offer the services for which we rely on them at economically reasonable terms or at
all, devote the resources necessary to expand our reach, increase our distribution, or support an increased number of users and associated use cases. Our dependence on any
single third-party supplier increases when our supply of a particular service is more heavily concentrated with that third-party. Some of our strategic partners offer, or could offer,
competing products and services or also work with our competitors, the likelihood of which may increase due to the ongoing shift toward remote work. As a result of these factors,
many of our third-party partners may choose to develop or support alternative products and services in addition to, or in lieu of, our work marketplace, either on their own or in
collaboration  with  others,  including  our  competitors.  If  we  are  unsuccessful  in  establishing  or  maintaining  our  relationships  with  third  parties  on  favorable  terms,  our  ability  to
compete  or  to  grow  our  total  revenue  could  be  impaired  and  our  operating  results  may  be  adversely  impacted.  Even  if  we  are  successful  in  establishing  and  maintaining  these
relationships with third parties on favorable terms, we cannot ensure that these relationships will result in increased usage of our work marketplace or increased revenue.

We are subject to disputes with or between users of our work marketplace.

Our  business  model  involves  enabling  connections  between  talent  and  clients  that  contract  directly  through  our  work  marketplace.  Talent  and  clients  are  free  to  negotiate  any
contract terms they choose, but we also provide optional service contract terms that they can elect to use. Disputes sometimes arise between talent and clients with regard to their
contract  terms,  work  relationship,  or  otherwise,  including  with  respect  to  service  standards,  payment,  confidentiality,  work  product,  and  intellectual  property  ownership  and
infringement. These disputes may occur more frequently during a macroeconomic downturn. If either party believes the contract terms were not met, our standard terms and some
individually negotiated services agreements provide a mechanism for the parties to request assistance from us, and, for some contracts, if that is unsuccessful, they may choose to
resolve the dispute with the help of a third-party arbitrator. Whether or not talent and clients decide to seek assistance from us, if these disputes

19

are not resolved amicably, the parties might escalate to formal proceedings, such as by filing claims with a court or arbitral authority. Given our role in facilitating and supporting
these arrangements, claims are sometimes brought against us directly as a result of these disputes and talent or clients bring us into any claims filed against each other, particularly
when the other user is insolvent or facing financial difficulties. Through our terms of service and services agreements for premium offerings, we disclaim responsibility and liability for
any  disputes  between  users  (except  with  respect  to  specified  dispute  assistance  programs  and  services);  however,  we  cannot  guarantee  that  these  terms  will  be  effective  in
preventing  or  limiting  our  involvement  in  user  disputes  or  that  these  terms  will  be  enforceable  or  otherwise  effectively  prevent  us  from  incurring  liability  as  a  result  of  disputes
between users. In addition, from time to time users assert claims against us regarding their experience on our work marketplace, including related to their search ranking results,
their feedback ratings, our advertising or marketing, our dispute resolution process, or admission or non-admission to the work marketplace or other programs and badges, including
those designed to highlight successful talent. Moreover, for some premium offerings, we provide enhanced services and assistance with respect to disputes over work product, and
clients or talent may pursue claims against us if they are not satisfied with those enhanced services. Disputes between clients and talent and between users and our company may
become more frequent based on conditions outside our control, such as a macroeconomic downturn. Such disputes, or any increase in the number of disputes, may result in an
adverse effect on our company, such as a loss of goodwill with users, reputational harm, lost GSV and revenue, and an increase in costs to us. Even if these claims do not result in
litigation  or  are  resolved  in  our  favor,  these  claims,  and  the  time  and  resources  necessary  to  resolve  them,  could  result  in  legal,  settlement,  or  other  financial  costs;  divert  the
resources of our management; and adversely affect our business and operating results.

Our  business  depends  largely  on  our  ability  to  attract  and  retain  talented  employees,  including  senior  management  and  key  personnel.  If  we  lose  the  services  of
Hayden Brown, our President and Chief Executive Officer, or other members of our senior management team or key personnel, we may not be able to execute on our
business strategy.

Our future success depends in large part on the continued services of senior management and other key personnel and our ability to attract, retain, and motivate them. In particular,
we are dependent on the services of Hayden Brown, our President and Chief Executive Officer, and our future vision, strategic direction, work marketplace, and technology could be
compromised if she were to take another position, become ill or incapacitated, or otherwise become unable to serve as our President and Chief Executive Officer. We rely on our
leadership  team  and  other  key  personnel  in  the  areas  of  product,  engineering,  operations,  security,  marketing,  sales,  support,  corporate  development,  and  general  and
administrative functions. Our senior management and other key personnel are all employed on an at-will basis, which means that they could terminate their employment with us at
any time, for any reason, and without notice, and we do not maintain any “key-person” life insurance policies. If we lose the services of senior management or other key personnel, if
our succession plans prove inadequate, or if we are unable to retain, attract, train, and integrate the highly skilled personnel we need, our business, operating results, and financial
condition could be adversely affected.

We have made, and may continue to make, changes that have been and will be disruptive to our personnel, such as changes to the composition of our leadership team and other
key personnel and reorganizations of reporting lines of our workforce. These changes have resulted, and future personnel changes may result, in increased attrition or reduced
productivity of our personnel, including senior management and key personnel, stemming from organizational restructuring, as new reporting relationships are established, and as
other companies may increasingly target our executives and other key personnel, particularly during the current highly competitive market for qualified personnel. Any such changes
may also result in a loss of institutional knowledge, cause disruptions to our business, impede our ability to achieve our objectives, or distract or result in diminished morale in, or the
loss of, workers.

Our future success also depends on our continuing ability to retain, attract, train, and integrate highly skilled personnel, including software engineers and sales personnel. We face
intense competition for qualified personnel from numerous software and other technology companies. In addition, competition for qualified software engineers is particularly intense.
This competition has become exacerbated by the increase in employee resignations currently taking place throughout the United States as a result of the COVID-19 pandemic,
which is commonly referred to as the “great resignation.” We may not be able to retain our current key personnel or attract, train, integrate, or retain other highly skilled personnel in
the future, all of which may be more difficult given our shift to a flexible work model for our workforce. We may incur significant costs to attract and retain highly skilled personnel, we
may lose employees to our competitors or other technology companies before we realize the benefit of our investment in recruiting and training them, and our succession plans may
be insufficient to ensure business continuity if we are unable to retain key personnel or were to lose a significant portion of our personnel. Further, even highly skilled

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personnel may fail to be productive, and our adoption of remote work may result in a loss of productivity of our workforce. To the extent we move into new geographies, including
internationally, we would need to attract and recruit skilled personnel in those areas.

Volatility or lack of appreciation in our stock price may also affect our ability to attract new skilled personnel and retain our key personnel. The market price of our common stock has
been,  and  may  continue  to  be,  particularly  volatile,  in  part  due  to  broader  stock  market  fluctuations,  and  as  a  result,  the  equity  held  by  our  senior  management  and  other  key
personnel  may  have  depreciated  in  value  relative  to  the  original  purchase  or  issue  price  and  therefore  have  less  retentive  power.  If  we  are  unable  to  attract  and  retain  suitably
qualified  individuals  who  are  capable  of  meeting  our  growing  technical,  operational,  and  managerial  requirements,  on  a  timely  basis  or  at  all,  or  if  we  need  to  increase  our
compensation expense to retain our employees, our business, operating results, financial condition, and cash flows may be adversely affected.

Clients sometimes fail to pay their invoices, necessitating action by us to compel payment.

In  connection  with  our  Upwork  Enterprise  offering,  and  for  certain  legacy  clients,  we  advance  payments  to  talent  for  invoiced  services  on  behalf  of  the  client  and  subsequently
invoice the client for such services. In order to maintain these relationships, we have in the past been, and may in the future be, forced to agree to terms that are unfavorable to us,
including  extended  payments  terms.  In  addition,  in  certain  instances,  we  will  advance  payment  on  a  talent  invoice  if  the  client  issues  a  chargeback  or  their  payment  method  is
declined and the talent assigns us the right to recover any funds from the client. From time to time, clients fail to pay for services rendered by talent, and as a result, we may be
adversely affected both from the inability to collect amounts due and the cost of enforcing the applicable agreement or our terms of service, including through arbitration or litigation.
Furthermore, some clients may seek bankruptcy protection or other similar relief and fail to pay amounts due, or pay those amounts more slowly, either of which could adversely
affect our operating results, financial position, and cash flow. All of these risks are made more likely during a macroeconomic downturn and could result in increased costs to us as
we advance payments to talent and seek to compel payment from our clients.

We may be unable to integrate acquired businesses and technologies successfully or to achieve the expected benefits of such acquisitions. We may acquire or invest
in additional companies, which may divert our management’s attention, result in additional dilution to our stockholders, and consume resources that are necessary to
sustain our business.

Our business strategy may, from time to time, include acquiring complementary products, technologies, businesses, or other assets. We also may enter into relationships with other
businesses to expand our work marketplace or our ability to provide our work marketplace in foreign jurisdictions, which could involve preferred or exclusive licenses, additional
channels of distribution, discount pricing, or investments in other companies. Negotiating these transactions can be time-consuming, difficult, and expensive, and our ability to close
these transactions may often be subject to approvals that are beyond our control. Consequently, these transactions, even if undertaken and announced, may not close, and any
acquisition, investment, or business relationship may result in unforeseen or additional operating difficulties, risks, and expenditures. For one or more of those transactions, we may:

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use cash that we may need in the future to operate our business;

become subject to different laws and regulations due to the nature or location of the acquired business, products, technologies, or other assets, or become subject to more
stringent scrutiny or differing applications of laws and regulations to which we are currently subject as a result of such transactions;

issue additional equity or convertible debt securities that would dilute our stockholders’ ownership interest;

incur expenses or assume substantial liabilities;

encounter difficulties retaining key personnel of the acquired company or integrating diverse software codes, operations, or business cultures;

encounter difficulties in assimilating acquired operations and development cultures or otherwise fail to realize the anticipated benefits of such transactions;

encounter diversion of management’s attention to other business concerns;

become subject to adverse tax consequences, substantial depreciation, or deferred compensation charges;

incur debt on terms unfavorable to us or that we are unable to repay; or

be required to adopt new, or change our existing, accounting policies.

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Any of these risks could adversely impact our business and operating results.

Risks Related to Our Industry, Offerings, and Services

Because  we  derive  the  substantial  majority  of  our  revenue  from  our  marketplace  offerings—with  most  of  our  marketplace  revenue  derived  from  our  Upwork  Basic,
Plus, and Enterprise offerings—our inability to generate revenue from our marketplace offerings would adversely affect our business operations, financial results, and
growth prospects.

We derive, and expect to continue to derive in the near future, the substantial majority of our revenue from our marketplace offerings, with most of our marketplace revenue derived
from our Upwork Basic, Plus, and Enterprise offerings. As such, market acceptance of our marketplace offerings, including new offerings, is critical to our continued success, and
any failure of our marketplace offerings to meet users’ expectations with respect to user experience or the failure of specific features to be effective in attracting and retaining users
will have a negative impact on our business. Demand for our marketplace offerings is affected by a number of factors beyond our control, including the timing and success of new
offerings and services by our competitors, our ability to respond to technological change and to effectively innovate and grow, contraction in our market, client spending patterns,
talent activity levels, the size and price of projects on our work marketplace, changes in adoption of remote work, macroeconomic effects, such as those resulting from the COVID-
19 pandemic, and the other risks identified herein. If we are unable to meet user demands, to expand our offerings or the categories of services offered on our work marketplace, or
to  achieve  and  maintain  more  widespread  market  acceptance  of  our  marketplace  offerings,  our  business  operations,  financial  results,  and  growth  prospects  will  be  adversely
affected.

We face intense competition and could lose market share to our competitors, which could adversely affect our business, operating results, and financial condition.

The market segment for independent talent and the clients that engage them is highly competitive, rapidly evolving, fragmented, and subject to changing technology, shifting needs,
and  frequent  introductions  of  new  competitors  as  well  as  new  offerings  and  services.  The  level  of  competition  within,  and  the  frequency  and  likelihood  of  increased  third-party
investment and new competitors entering, this market segment has further intensified due to the ongoing COVID-19 pandemic and the resulting shift toward remote work and other
labor market dynamics. We compete with a number of online and offline platforms and services domestically and internationally, as well as traditional staffing firms, to attract and
retain users and expand our share of user spend. Our main competitors fall into the following categories:

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traditional contingent workforce and staffing service providers and other outsourcing providers, such as The Adecco Group, Randstad, Recruit, Allegis Group, and Robert
Half International;

online freelancer platforms that serve either a diverse range of skill categories, such as Fiverr, Guru, and Freelancer.com, or specific skill categories;

other online providers of products and services for individuals or businesses seeking work or to advertise their services, including personal and professional social networks,
such  as  LinkedIn  and  GitHub  (each  owned  by  Microsoft),  employment  marketplaces,  platforms  providing  compliance  services,  recruiting  websites,  and  project-based
deliverable providers;

software and business services companies focused on talent acquisition, management, invoicing, or staffing management products and services, such as Workday;

payment businesses, such as PayPal and Payoneer, that can facilitate payments to and from businesses and service providers;

businesses that provide specialized professional services, including consulting, accounting, marketing, and information technology services; and

online  and  offline  job  boards,  classified  ads,  and  other  traditional  means  of  finding  work  and  service  providers,  such  as  Craigslist,  CareerBuilder,  Indeed,  Monster,  and
ZipRecruiter.

In addition, well-established internet companies, such as Google, LinkedIn, and Amazon, social media platforms, such as Meta, and businesses that operate driving, delivery, and
other commoditized marketplaces, such as Uber Technologies, have entered or may decide to enter into our market segment. Some of these companies have launched or may
launch, or have acquired or may acquire companies or assets that offer products and services that directly compete with our work marketplace. For example, LinkedIn launched
ProFinder in 2016 and Open for Business in 2019, and in 2021 launched a new offering called Services Marketplaces, each of which is a service to connect LinkedIn members with
one another for freelance service relationships. Many of these established internet

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companies and other competitors are considerably larger than we are, have considerably greater financial and other resources than we do, and could offer products and services
similar to our offerings for lower fees.

Internationally,  we  compete  against  online  and  offline  channels  and  products  and  services  in  most  countries.  Local  competitors,  or  competitors  that  have  invested  more  in
international expansion, might have greater brand recognition than us in other countries and a stronger understanding of local or regional culture and commerce. Some competitors
also offer their products and services in local languages and currencies that we do not offer. As our business grows internationally and we expand and grow our services offerings,
we  may  increasingly  compete  with  these  international  companies.  We  also  compete  against  locally  sourced  service  providers  and  traditional,  offline  means  of  finding  work  and
procuring services, such as staffing businesses, personal and professional networks, classified ads, and recruiters.

We also compete with companies that utilize emerging technologies and assets, such as blockchain, artificial intelligence, augmented reality, cryptocurrency, and machine learning.
These competitors may offer products and services that may, among other things, provide automated alternatives to the services that talent provide on our work marketplace, use
machine  learning  algorithms  to  connect  businesses  with  service  providers  more  effectively  than  we  do,  or  otherwise  change  the  way  that  businesses  engage  or  pay  service
providers so as to make our work marketplace less attractive to users. Many of the companies and services that utilize these technologies in our market are still new and not yet
fully mature in their capabilities or network scale; however, we may face increased competition should these companies or services, or new entrants, succeed.

Many  of  our  current  and  potential  competitors,  both  online  and  offline,  enjoy  substantial  competitive  advantages,  such  as  greater  name  recognition  and  more  prominent  brand
reputation;  pre-existing  relationships  with  desirable  clients;  more  experience  with  international  operations  and  localization  of  their  offerings;  longer  operating  histories;  greater
financial, technical, and other resources; more users; newer technologies; greater appeal to certain segments of users, such as those entering the workforce; and, in some cases,
the ability to rapidly combine online platforms with traditional staffing and contingent worker solutions. These companies may use these advantages to offer products and services
similar to ours at a lower price, develop different or superior products and services to compete with our work marketplace, or respond more quickly and effectively than we do to new
or changing opportunities, technologies, standards, regulatory conditions, or user preferences or requirements. In addition, while we compete intensely in more established markets,
we also compete in developing technology markets that are characterized by dynamic and rapid technological change, many and different business models, and frequent disruption
of incumbents by innovative online and offline entrants. The barriers to entry into these markets can be low, and businesses easily and quickly can launch online or mobile platforms
and applications at nominal cost by using commercially available software or partnering with various established companies in these markets.

Moreover,  current  and  future  competitors  may  also  make  strategic  acquisitions  or  establish  cooperative  relationships  among  themselves  or  with  others,  including  our  current  or
future third-party partners. By doing so, these competitors may increase their ability to meet the needs of our existing or prospective users. These developments could limit our
ability to obtain revenue from existing and new users. For all of these reasons, we may not be able to compete successfully against our current and future competitors. If we are
unable to compete successfully against current and future competitors, our business, operating results, and financial condition would be adversely impacted.

If we fail to develop, maintain, and enhance our brand and reputation cost-effectively, our business and financial condition may be adversely affected.

We  believe  that  developing,  maintaining,  evolving,  and  enhancing  awareness  and  integrity  of  our  brand  and  reputation  in  a  cost-effective  manner  are  important  to  achieving
widespread acceptance and use of our work marketplace and are important elements in attracting new users and retaining existing users. Successful promotion and positioning of
our  brand,  offerings,  and  business  model  depend  on,  among  other  things,  the  effectiveness  of  our  marketing  efforts  and  brand  messaging,  our  ability  to  provide  a  reliable,
trustworthy, and useful work marketplace and offerings at competitive prices, the perceived value of our work marketplace and offerings, and our ability to provide quality support. In
order  to  reach  the  brand  awareness  and  acceptance  levels  of  some  of  our  competitors,  we  need  to  continuously  invest  in  marketing  programs  that  may  not  be  successful  in
achieving meaningful awareness and acceptance levels, particularly during early phases of expansion into newer user awareness segments, such as international users. Some of
the marketing programs and brand promotion efforts we implement may be new and unproven and therefore their likelihood of success may be uncertain. Further, brand promotion
activities may not resonate with existing or potential users or yield increased revenue, and even if they do, the increased revenue may not offset the expenses we incur in building,
evolving, and maintaining our brand and reputation. For example, since 2019, we have made significant investments in sales and marketing to acquire new

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clients  and  drive  brand  awareness,  and  expect  to  increase  these  investments  throughout  2022.  It  is  not  certain  that  these  investments  have  had  or  will  have  sufficient  positive
impact on our brand to be cost effective. Likewise, publicity efforts or news coverage may undermine our brand promotion efforts or harm our reputation or may not resonate with
existing or potential users. We have also recently evolved, and will continue to evolve, our marketing and brand positioning efforts, including a rebranding effort which we undertook
in the second quarter of 2021, expanding our focus on large enterprise and other clients and prospects with larger, longer-term independent talent needs. These efforts may not be
successful in achieving the brand awareness and acceptance levels in a cost-effective manner, or without harming other areas of our business.

We also rely on our community of users in a variety of ways, including their willingness to give us feedback regarding our work marketplace, and failure of our users to provide
feedback on their experience on our work marketplace or our failure to adequately address any concerns could negatively impact the willingness of them or prospective users to use
our work marketplace. For example, the prior changes made in the pricing and packaging of Connects purchases resulted in user dissatisfaction and negatively impacted fill rates
for projects on our work marketplace for a period of time. If we fail to promote and maintain our brand successfully, address user concerns, or to maintain loyalty among our users,
or if we incur substantial expenses in unsuccessful attempts to promote and maintain our brand, we may fail to attract new users or retain our existing users and our business and
financial condition may be adversely affected.

If the market for independent talent and the services they offer develops more slowly than we expect, our growth may slow or stall, and our operating results could be
adversely affected.

The market for online independent talent and the services they offer is relatively new, rapidly evolving, and unproven. Our future success will depend in large part on the continued
growth and expansion of this market and the willingness of businesses to engage independent talent to provide services and independent talent to engage as service providers. It is
difficult to predict the size, growth rate, and expansion of this market, whether any expansion will be long-term or temporary, particularly as the COVID-19 pandemic subsides and
restrictions  intended  to  prevent  its  spread  are  relaxed  or  lifted,  the  success  of  competitive  products  and  services,  or  technological,  macroeconomic,  legal,  regulatory,  or  other
developments that will impact the overall demand for independent talent. Furthermore, many businesses may be unwilling to engage independent talent for a variety of reasons,
including  perceived  negative  connotations  with  outsourcing  work,  quality  of  work,  or  privacy  or  data  security  concerns  or  the  rapidly  evolving  regulations  that  may  impact  the
demand for independent contractor services more generally, including as discussed further in the risk factor titled “There may be adverse tax, legal, and other consequences if the
contractor classification or employment status of talent that use our work marketplace is challenged.” Likewise, with the greater adoption of remote work and increased flexibility in
employment relationships resulting from the COVID-19 pandemic, more skilled independent talent may choose traditional employment. If the market for independent talent and the
services they offer does not achieve widespread adoption, or there is a reduction in demand for independent talent, including as the COVID-19 pandemic subsides, it could result in
decreased revenue and our business could be adversely affected.

If we are not able to develop and release new offerings and services, or develop and release successful enhancements, new features, and modifications to our existing
offerings and services, our business could be adversely affected.

The market for our work marketplace is characterized by rapid technological change, frequent product and service introductions and enhancements, changing user demands, and
evolving industry standards. The introduction of offerings and services embodying new technologies can quickly make existing offerings and services obsolete and unmarketable.
We  invest  substantial  resources  in  researching  and  developing  new  offerings  and  services  and  enhancing  our  work  marketplace  by  incorporating  additional  features,  improving
functionality, modernizing our technology, and adding other improvements to meet our users’ evolving demands in our increasingly highly competitive industry. For example, in 2020
we invested a significant amount of resources to launch Project Catalog and we continue to invest resources to modify and enhance this and other offerings to increase client traffic
and usage and improve the user experience. The success of any enhancements or improvements to, or new features of, our work marketplace or any new offerings and services,
such as Project Catalog, depends on several factors, including overall demand and market acceptance consistent with the intent of such offerings or services, competitive pricing,
adequate quality testing to ensure an absence of errors, defects, and disruptions on our work marketplace, integration with new and existing technologies on our work marketplace
and third-party partners’ technologies, and timely completion. We cannot be sure that we will succeed, on a timely or cost-effective basis, in developing, marketing, and delivering
enhancements or new features to or modernizing our work marketplace or any new offerings and services that respond to continued changes in the market for independent talent or
business services. Any enhancements or new features to our work marketplace or any new offerings and services may not achieve,

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and  in  the  past  certain  features  and  offerings  have  not  achieved,  market  acceptance,  cost-effectiveness,  or  the  intended  effect.  In  the  past,  we  have  experienced  unintended
negative effects, including reduced client spend, diminished fill rates for projects on our work marketplace, errors and disruptions on our work marketplace, and user dissatisfaction
from certain modifications to our offerings, services, and features.

Moreover, even if we introduce new offerings and services, we may experience a decline in revenue from our existing offerings and services that is not offset by revenue from the
new offerings or services. In addition, we may lose existing users that choose to use competing products or services. This could result in a temporary or permanent decrease in
revenue and adversely affect our business.

Because a substantial portion of the services offered by talent and sought by clients on our work marketplace is information technology services, a decline in talent
offering information technology services or the market for information technology service providers on our work marketplace could adversely affect our business.

A substantial portion of the services offered by talent and sought by clients on our work marketplace relates to information technology. If, for any reason, the market for information
technology services declines, including as a result of the relaxation or lifting of restrictions intended to prevent the spread of COVID-19, a macroeconomic downturn, geopolitical
events, increased use of artificial intelligence, automation, or otherwise, if a sufficient number of qualified talent is not available on our work marketplace or willing to perform these
services or businesses satisfy their needs for these services through alternative means, including through use of our competitors’ products or traditional employment relationships,
or if the talent on our work marketplace are not located or able to work in specific geographic regions in which clients are seeking to engage remote talent, the growth in the number
of users on our work marketplace may slow or decline and as a result our revenue and business may be adversely impacted.

If  we  or  our  third-party  partners  experience  a  security  breach,  other  hacking  or  phishing  attack,  ransomware  or  other  malware  attack,  or  other  privacy  or  security
incident, whether intentionally or unintentionally caused by us or by third parties, our work marketplace may be perceived as not being secure, our reputation may be
harmed, demand for our work marketplace may be reduced, our operations may be disrupted, we may incur significant legal costs, fines, or liabilities, and our business
could be adversely affected.

Our business involves the storage, processing, and transmission of users’ proprietary, confidential, and personal information as well as the use of third-party partners and vendors
who store, process, and transmit users’ proprietary, confidential, and personal information. We also maintain certain other proprietary and confidential information relating to our
business and personal information of our personnel. Our systems, and the systems of our vendors and third-party partners, may be vulnerable to privacy or security incidents, such
as computer viruses and other malicious software, physical or electronic break-ins, or vulnerabilities resulting from intentional or unintentional service provider actions, and similar
disruptions  that  could  make  all  or  portions  of  our  website  or  applications  unavailable  for  periods  of  time.  Any  privacy  or  security  incident,  whether  intentionally  or  unintentionally
caused by us or by third parties, that we experience could result in unauthorized access to, misuse of, or unauthorized acquisition of our, our personnel’s, or our users’ data; the
loss, corruption, or alteration of this data; interruptions in our operations; or damage to our computers or systems or those of our users. Any of these could expose us to claims,
litigation, fines, enforcement actions, other potential liability, and reputational harm. Additionally, ransomware or other malware, viruses, social engineering (including business email
compromise and related wire-transfer fraud), and general hacking in our industry have become more prevalent and more complex. Bad actors often try to take advantage of us, our
users,  and  our  vendors  and  third-party  partners  by  using  social  engineering  and  other  methods  to  persuade  their  victims  to  make  fraudulent  payments,  or  to  download  viruses,
ransomware, or other malware into computer systems and networks. Because the techniques used to obtain unauthorized access, disable or degrade service, or sabotage systems
change  frequently  and  often  are  not  foreseeable  or  recognized  until  launched  against  a  target,  we  and  our  vendors  and  third-party  partners  may  be  unable  to  anticipate  these
techniques or to implement adequate preventative measures, despite our efforts to implement and maintain a robust information security program. Data security breaches and other
privacy and security incidents may also result from non-technical means, such as, for example, actions taken by employees or contractors, such as talent that we engage on our
work  marketplace  to  perform  services  for  us,  and  the  likelihood  of  such  incidents  may  increase  as  a  result  of  our  workforce  working  remotely.  If  we,  our  vendors,  or  third-party
partners experience an actual or perceived breach or privacy or security incident, public perception of the effectiveness of our security measures and brand could be harmed, and
we could lose users and business. In addition, significant unavailability of our work marketplace due to security breaches or other privacy and security incidents could cause users
to decrease their use of or cease using our work marketplace. Any of these effects could adversely impact our business.

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Any compromise of our security or the security of our vendors or third-party partners could result in a violation of applicable privacy and other laws, regulatory or other governmental
investigations, enforcement actions, litigation, and legal and financial exposure, including potential contractual liability. We may also need to expend significant resources to protect
against, and to address issues created by, security breaches and other privacy and security incidents. While we maintain cyber liability insurance, these liabilities may exceed the
amounts covered by our insurance; further, we cannot be certain that our insurance coverage will extend to or be adequate for liabilities actually incurred, or that insurance will
continue to be available to us on economically reasonable terms, at coverage limits we deem prudent, or at all. Any such compromise could also result in damage to our reputation
and a loss of confidence in our security measures.

Depending on the nature of the information compromised, in the event of a security breach or other privacy or security incident, we may also have obligations to notify affected
individuals and entities and regulators about the incident, and we may need to provide some form of remedy, such as a subscription to credit monitoring services, pay significant
fines to one or more regulators, or pay compensation in connection with a class-action settlement (including under the private right of action under the California Consumer Privacy
Act  of  2018,  which  we  refer  to  as  the  CCPA).  Such  breach  notification  laws  continue  to  evolve  and  may  be  inconsistent  from  one  jurisdiction  to  another.  Complying  with  these
obligations  could  cause  us  to  incur  substantial  costs  and  could  increase  negative  publicity  surrounding  any  incident  that  compromises  our,  our  users’,  our  employees’,  our
contractors’, or other confidential, proprietary, or personal information.

Our  sales  efforts  are  increasingly  primarily  targeted  at  large  enterprise  and  other  clients  and  prospects  with  larger,  longer-term  independent  talent  needs,  and  as  a
result we may encounter greater pricing, implementation, and customization challenges, and we may incur additional costs, each of which could adversely impact our
business and operating results.

Our sales efforts are primarily targeted at large enterprise and other clients and prospects with larger, longer-term independent talent needs. For example, in the fourth quarter of
2021, we began increasing our investment in sales by expanding our sales team and we expect this expansion to continue through 2022 as we increase our efforts to acquire clients
of our Upwork Enterprise offering. As a result of our increased focus on these larger clients, we face greater costs, longer sales cycles, and less predictability in completing some of
our sales and in increasing spend by existing clients. For larger clients, use of our work marketplace may require approvals by multiple departments and executive-level personnel
and require us to provide greater levels of services and client education regarding the uses, benefits, security, privacy, worker classification, payments, and compliance services
offered on our work marketplace. Larger enterprises typically have longer decision-making and implementation cycles and may demand more customization, greater indemnification
and risk shifting, higher levels of support, a broader range of services, and greater payment flexibility. In addition, larger clients may require greater functionality and scalability that
can lead to delays in sales or difficulties in growing client spend. We are often required to spend time and resources to better familiarize potential large enterprise clients with the
value propositions of our work marketplace generally. Despite our efforts in familiarizing potential large enterprise clients with the benefits of our work marketplace, these potential
clients  may  decide  not  to  use  our  work  marketplace  if,  among  other  reasons,  they  do  not  feel  that  their  procurement  or  compliance  needs  are  or  will  be  met.  In  addition,  sales
opportunities with large clients may require us to devote greater sales and administrative support and professional services resources to individual clients, which could increase our
costs,  lengthen  our  sales  cycle,  and  divert  our  own  sales  and  professional  services  resources  to  a  smaller  number  of  larger  clients.  We  may  spend  substantial  time,  effort,  and
money in our sales efforts without being successful in producing sales or growing client spend.

Even if we reach an agreement with a client to use our work marketplace, the agreement may not be on pricing or other terms that are favorable to us. A significant portion of the
fees we typically receive from clients is contingent on the level of spend by the client. If a client negotiates pricing terms that are less favorable to us, does not engage talent on our
work marketplace, or uses talent for few projects or projects of low value, our revenue from the relationship may be minimal.

If internet search engines’ methodologies or other channels that we utilize to direct traffic to our website are modified to our disadvantage, or our search result page
rankings decline for other reasons, our user growth could decline.

We depend in part on various internet search engines, such as Google, as well as other channels to direct a significant amount of traffic to our website. Our ability to maintain the
number of visitors directed to our website is not entirely within our control. For example, our competitors’ search engine optimization and other efforts such as paid search may
result in their websites receiving a higher search result page ranking than ours, internet search engines or other channels that we utilize to direct traffic to our website have in the
past and could again revise their

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methodologies  or  implement  other  changes  or  penalties  that  adversely  impact  traffic  to  our  website,  or  we  may  make  changes  to  our  website  that  adversely  impact  our  search
engine optimization rankings and traffic to our website in order to comply with applicable regulatory requirements or for other reasons. As a result, links to our website may not be
prominent enough to drive sufficient traffic to our website, and we may not be able to influence the results.

Search engines and other channels that we utilize to drive users to our website periodically change their algorithms, policies, and technologies, sometimes in ways that cause traffic
to our website to decline. These changes can also result in an interruption in users’ ability to access our website or a drop in our search ranking, or have other adverse impacts that
negatively affect our ability to maintain and grow the number of users that visit our website. We may also be forced to significantly increase marketing expenditures in the event that
market  prices  for  online  advertising  and  paid  listings  escalate  or  our  organic  ranking  decreases.  Any  of  these  changes  could  have  an  adverse  impact  on  our  business,  user
acquisition, and operating results.

Users circumvent our work marketplace, which adversely impacts our business.

Our business depends on users transacting through our work marketplace. Despite our efforts to prevent them from doing so, users circumvent our work marketplace and engage
with or take payment through other means to avoid the fees that we charge, and it is difficult or impossible to measure the losses associated with circumvention. Enhancements and
changes we make with respect to our offerings, services, and features may unintentionally cause, and may have unintentionally caused in the past, users to circumvent our work
marketplace. In addition, circumvention by users of our work marketplace is likely to increase during a macroeconomic downturn, as users may be more cost-sensitive with respect
to our fees. Moreover, certain changes we make to decrease circumvention by users have in the past and could again inadvertently result in user dissatisfaction, increased user
circumvention, and a decline in user activity on our work marketplace. The loss of revenue associated with circumvention of our work marketplace has an adverse impact on our
business,  cash  flows,  operating  results,  and  financial  condition.  In  addition,  our  efforts  to  reduce  circumvention  may  be  costly  or  disruptive  to  implement,  have  results  that  are
difficult or impossible to measure, fail to have the intended effect or have an adverse effect on our brand or user experience, cause users to cease using our work marketplace,
reduce the attractiveness of our work marketplace, divert the attention of management, or otherwise harm our business.

Errors, defects, or disruptions in our work marketplace could diminish demand, adversely impact our financial results, and subject us to liability.

Our work marketplace enables our users to manage important aspects of their businesses, and any errors, defects, or disruptions in our work marketplace, or other performance or
availability problems with our work marketplace or infrastructure could harm our brand and reputation, negatively impact our operating results, or otherwise damage our business or
the businesses of our users. As the usage of our work marketplace grows, and as we introduce new offerings and services and look to expand our international footprint over time,
we will need an increasing amount of technical infrastructure and continued infrastructure modernization, including network capacity and computing power, to continue to operate
our  work  marketplace.  We  may  fail  to  effectively  scale  and  grow  our  technical  infrastructure  to  accommodate  these  increased  demands,  which  may  adversely  affect  our  user
experience. We also rely on third-party software and infrastructure, including the infrastructure of the internet, to provide our work marketplace. Any failure of or disruption to this
software  and  infrastructure  could  also  make  our  work  marketplace  unavailable  to  our  users.  For  example,  these  types  of  disruptions  have  negatively  impacted  our  work
marketplace,  such  as  an  inadvertent  error  by  a  regulatory  agency  that  prevented  users  from  accessing  our  website  for  a  brief  period  of  time.  Internet  shutdowns  in  certain
jurisdictions  are  becoming  more  frequent,  including  in  response  to  civil  unrest  or  prior  to  contested  political  elections,  and  any  shutdown  in  a  jurisdiction  in  which  a  significant
number of our users are located will adversely affect user activity on our work marketplace throughout the duration of such shutdown. Our work marketplace is constantly changing
with new updates, which may contain undetected errors when first introduced or released. Any errors, defects, disruptions in service, or other performance or stability problems with
our work marketplace, or the inadequacy of our efforts to adequately prevent or timely detect or remedy errors or defects, could result in negative publicity, loss of or delay in market
acceptance of our work marketplace, loss of competitive position, our inability to timely and accurately maintain our financial records, interference with our clients’ ability to contract
for,  or  the  ability  of  talent  to  complete,  projects  on  our  work  marketplace,  inaccurate  or  delayed  invoicing  of  clients,  delay  of  payment  to  us  or  talent,  claims  by  users  for  losses
sustained  by  them,  or  investigation  and  corrective  action  taken  by  regulatory  agencies.  In  such  an  event,  we  may  be  required,  or  may  choose,  for  customer  relations  or  other
reasons, to expend additional resources in order to help resolve the issue. Accordingly, any errors, defects, or disruptions in our work marketplace could adversely impact our brand
and reputation, revenue, and operating results.

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Our ability to attract and retain users is dependent in part on ease of use and reliability of our work marketplace and the quality of our support, and any failure to offer
high-quality support could adversely impact our business, operating results, and financial condition.

Our ability to attract and retain users is dependent in part on the ease of use and reliability of our work marketplace, including our ability to provide high-quality support. Our users
depend on our support organization to resolve any issues relating to our work marketplace, to communicate effectively about their accounts, and to assist in their use of our work
marketplace, especially large enterprise clients, which expect higher levels of support. Our ability to provide effective support is largely dependent on our ability to attract, resource,
and retain service providers who are both qualified to support users of our work marketplace and well versed in our work marketplace. Offering our website and user support only in
English may negatively impact our relationships with our users, particularly users in non-English speaking countries. As we seek to continue to grow our international user base, our
support organization will face additional challenges, including those associated with delivering support and documentation in languages other than English. Any failure to maintain
high-quality support or effectively communicate with our users, or any market perception that we do not maintain high-quality support or act professionally, fairly, or effectively in our
communications and actions with respect to users, could harm our reputation, adversely affect our ability to sell our work marketplace to existing and prospective users, and could
adversely impact our business, operating results, and financial condition.

We  rely  on  AWS  to  deliver  our  work  marketplace  to  our  users,  and  any  disruption  of  service  from  AWS  or  material  change  to  our  arrangement  with  AWS  could
adversely affect our business.

We  currently  host  our  work  marketplace,  serve  our  users,  and  support  our  operations  using  AWS,  a  provider  of  cloud  infrastructure  services.  We  do  not  have  control  over  the
operations of the facilities of AWS that we use. AWS’s facilities are vulnerable to failure, damage, or interruption from a number of causes, including from earthquakes, hurricanes,
floods, fires, cybersecurity attacks, terrorist attacks, power losses, telecommunications failures, and similar events or could be subject to break-ins, computer viruses, sabotage,
intentional  acts  of  vandalism,  and  other  misconduct.  The  occurrence  of  any  of  these  events,  a  decision  to  close  the  facilities  or  cease  or  limit  providing  services  to  us  without
adequate  notice,  or  other  unanticipated  problems  could  result  in  interruptions  to  our  work  marketplace,  including  lengthy  interruptions.  Our  work  marketplace’s  continuing  and
uninterrupted performance is critical to our success and users may become dissatisfied by any system failure that interrupts our ability to provide our work marketplace to them. We
may not be able to easily switch our AWS operations to another cloud or other data center provider if there are disruptions or interference with our use of AWS, and, even if we do
switch  our  operations,  other  cloud  and  data  center  providers  are  subject  to  the  same  risks.  Sustained  or  repeated  system  failures  could  reduce  the  attractiveness  of  our  work
marketplace to users, cause users to decrease their use of or cease using our work marketplace, and adversely affect our business. Moreover, negative publicity arising from these
types  of  disruptions  could  damage  our  reputation  and  may  adversely  impact  use  of  our  work  marketplace.  We  may  not  carry  sufficient  business  interruption  insurance  to
compensate us for losses that may occur as a result of any events that cause interruptions in our service and we cannot be certain that insurance will continue to be available to us
on economically reasonable terms, or at all.

AWS does not have an obligation to renew its agreements with us on commercially reasonable terms, or at all. If we are unable to renew our agreements or unable to renew on
commercially reasonable terms, our agreements are prematurely terminated, or we add additional infrastructure providers, we may experience costs or downtime in connection with
the transfer to, or the addition of, new data center providers. If these providers charge high costs for or increase the cost of their services, we may have to increase the fees to use
our work marketplace and our operating results may be adversely impacted. In the second quarter of 2021 we substantially completed the transition to a different AWS facility in an
effort to reduce long-term costs, to gain access to servers with enhanced functionality, and increase operational resilience. The finalization of the migration is ongoing and during
this transition, we may incur additional costs, particularly if we encounter an unforeseen issue or incident as we complete the migration. We plan to complete the transition during
the first half of 2022.

In addition, we and other customers of AWS have been subject to litigation by third parties claiming that AWS and basic HTTP functions infringe their patents and may be subject to
such litigation again in the future. Such litigation has been, and may in the future continue to be, time consuming, and may divert management’s attention and adversely impact our
operating results.

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Our  user  growth  and  engagement  on  mobile  devices  depend  upon  third  parties  maintaining  open  application  marketplaces  and  effective  operation  with  mobile
operating systems, networks, and standards that we do not control.

Mobile devices are increasingly used for marketplace transactions. A significant and growing portion of our users access our work marketplace through mobile devices, including
through the use of mobile applications. Our mobile applications rely on third parties maintaining open application store platforms, including the Apple App Store and Google Play,
which make current and new applications or new versions of our mobile applications available for download and use on mobile devices. We cannot assure you that the platforms
through which we distribute our applications will maintain their current structures or terms of access, that such marketplaces will continue to make our mobile applications or newer
versions of our mobile applications available for download, or that such marketplaces will not charge us fees to list our applications for download, or charge us new or additional
fees to offer services and offerings through our applications. Additionally, there is no guarantee that popular mobile devices will continue to support our work marketplace, that the
use of mobile devices for payments or other transactions on our work marketplace will be available on commercially reasonable terms, or that mobile device users will use our work
marketplace rather than competing products. We are dependent on the interoperability of our work marketplace with popular mobile operating systems that we do not control, such
as Android and iOS, and any changes in such systems that degrade the functionality of our website or applications or give preferential treatment to competitors could adversely
affect the usage of our work marketplace on mobile devices. Additionally, in order to deliver high-quality mobile offerings, it is important that our offerings are designed effectively
and work well with a range of mobile devices, technologies, systems, networks, and standards that we do not control. We may not be successful in developing relationships with key
participants in the mobile industry or in developing offerings that operate effectively with these devices, technologies, systems, networks, or standards. In the event that it is more
difficult for our users to access and use our work marketplace on their mobile devices, our users find our mobile offering is not cost-effective, our users find our mobile offering does
not meet their needs, our competitors develop offerings and services that are perceived to operate more effectively on mobile devices, or our users choose not to access or use our
work  marketplace  on  their  mobile  devices  or  use  mobile  products  that  do  not  offer  access  to  our  work  marketplace,  our  user  growth,  user  engagement,  and  business  could  be
adversely impacted.

Risks Related to Legal and Regulatory Matters

We and our users may be subject to new and existing laws and regulations, both in the United States and internationally.

We and our users are subject to a wide variety of foreign and domestic laws. Laws, regulations, and standards governing issues that may affect us, such as worker classification,
employment, worker health, payments, worker confidentiality obligations and whistleblowing, intellectual property, consumer protection, taxation, privacy, and data security are often
complex and subject to varying interpretations, in many cases due to their lack of specificity, and, as a result, their enforcement and application in practice may change or develop
over time through judicial decisions or as new guidance or interpretations are provided by regulatory and governing bodies, such as federal and state administrative agencies. Many
of these laws were adopted prior to the advent of the internet, mobile, and related technologies and, as a result, do not contemplate or address the unique issues of the internet,
mobile, and related technologies. Other laws and regulations may be adopted in response to internet, mobile, and related technologies. New and existing laws and regulations (or
changes in interpretation of existing laws and regulations), including those concerning worker classification, independent contractors, employment, discrimination and harassment,
payments, whistleblowing and worker confidentiality obligations, intellectual property, consumer protection, taxation, privacy, data security, benefits, unionizing and collective action,
arbitration agreements and class action waiver provisions, unfair competition, terms of service, website accessibility, background checks (such as the Fair Credit Reporting Act, 15
U.S.C.  §  1681),  escheatment,  and  federal  contracting  may  also  be  adopted,  implemented,  or  interpreted  to  apply  to  us  and  other  online  services  marketplaces  or  our  users.
Likewise, these laws affect our users, and their application, or uncertainty around their application, may affect demand for our work marketplace.

New laws, regulations, and orders enacted in response to the COVID-19 pandemic or the resulting macroeconomic downturn and uncertainty may also affect our business in ways
that we do not anticipate, and existing laws and regulations may be interpreted and enforced differently than they have in the past in response to the pandemic. These laws may
change rapidly and compliance may be costly to us. On the other hand, a loosening of these restrictions as certain geographic areas continue to reopen may result in a decline in
user  activity  on  our  work  marketplace.  Likewise,  geopolitical  events,  such  as  recent  tensions  between  Ukraine  and  Russia,  may  cause  Russia,  Ukraine,  the  United  States,  the
United Kingdom, European Union, which we refer to as the EU, or other jurisdictions to implement new laws, regulations, or orders, or enforce existing laws, regulations, and orders,
in a

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manner that is harmful to us or our customers, including implementing sanctions that limit our ability engage with, collect payment from, or remit payment to, customers in Russia or
other jurisdictions.

As our work marketplace’s geographic scope expands, including efforts to increase adoption by users outside the United States and extending our physical presence internationally,
and as we expand or change the offerings and services offered on our work marketplace, regulatory agencies or courts may claim, or we may independently determine, that we, or
our users, are subject to additional regulations or requirements, or are prohibited from conducting our business, or conducting business with us, in or with certain jurisdictions, either
generally or with respect to certain offerings or services, or that we are otherwise required to change our business practices. If we determine additional legal requirements apply to
our business, we may expend resources to comply or obtain licenses to come into compliance with such requirements, and such efforts may be a distraction to the business or
require  adverse  changes  to  the  manner  in  which  we  conduct  our  business  or  our  work  marketplace  and  may  themselves  cause  regulatory  agencies  to  scrutinize  our  business,
including past practices. It is also possible that certain provisions in agreements with our users or service providers, or between talent and clients, or the fees we charge, may be
found to be unenforceable or not compliant with applicable law.

The level of regulatory scrutiny on larger companies, technology companies in general, and companies engaged in dealings with independent contractors, payments, or personal
information in particular, has increased significantly recently and may continue to increase. Legislators have enacted, and may continue to enact, new laws or regulatory agencies
may  promulgate  new  rules  or  regulations  that  are  adverse  to  our  business  or  the  interests  of  our  users,  or  they  may  view  matters  or  interpret  or  enforce  laws  and  regulations
differently than they have in the past or in a manner adverse to our business or the interests of our users. Such legislative or regulatory scrutiny or action may create or enhance
different or conflicting obligations on us from one jurisdiction to another.

New approaches to policy-making and legislation may also produce unintended harms to our business, which may impact our ability to operate our business in the manner in which
we are accustomed. For example, there has been increased focus on worker classification and independent contractor regulations which led in part to the adoption of legislation in
California, and it is possible that other jurisdictions will implement similar laws and regulations, as discussed in the risk factor titled “There may be adverse tax, legal, and other
consequences  if  the  contractor  classification  or  employment  status  of  talent  that  use  our  work  marketplace  is  challenged.”  These  types  of  laws  and  regulations  may  have  a  far-
reaching impact, including on the independent professionals that use our work marketplace and their clients. Any of these regulations could negatively impact our users, including
perceptions regarding their use of our work marketplace, or have a material adverse effect on the demand for talent on our work marketplace or on the manner in which we are able
to operate our work marketplace.

As we look to expand our international footprint over time, we may become obligated to comply with additional laws and regulations of the countries or markets in which we operate
or have users. We may be harmed if we are found to be subject to new or existing laws and regulations or if those laws are interpreted and applied to us in a manner that harms our
business or is inconsistent with the application of U.S. laws, including those concerning worker classification, independent contractors, employment, payments, whistleblowing and
worker confidentiality obligations, intellectual property, consumer protection, taxation, privacy, data security, benefits, unionizing and collective action, arbitration agreements and
class action waiver provisions, unfair competition, terms of service, website accessibility, background checks, and escheatment. In addition, contractual provisions that are designed
to protect and mitigate against risks, including terms of service, services agreements, arbitration and class action waiver provisions, disclaimers of warranties, limitations of liabilities,
releases  of  claims,  and  indemnification  provisions,  could  be  deemed  unenforceable  as  to  the  application  of  these  laws  and  regulations  by  a  court,  arbitrator,  or  other  decision-
making body. If we are unable to comply with these laws and regulations or manage the complexity of global operations and supporting an international user base successfully or in
a  cost-effective  manner,  or  if  these  laws  and  regulations  are  found  to  apply  to  our  users  or  cause  a  decline  in  demand  for  talent  services,  our  business,  operating  results,  and
financial condition could be adversely affected.

Having  an  international  community  of  users  and  engaging  talent  internationally  exposes  us  to  risks  that  could  have  an  adverse  effect  on  our  business,  operating
results, and financial condition, and these risks could increase as we seek to expand our international footprint.

Even though we currently have a limited physical presence outside of the United States, our users have a global footprint that subjects us to the risks of being found to do business
internationally.  We  have  users  of  our  work  marketplace  located  in  over  180  countries,  including  some  markets  where  we  have  limited  experience,  where  challenges  can  be
significantly  different  from  those  we  have  faced  in  more  developed  markets,  and  where  business  practices  may  create  greater  internal  control  risks.  Further,  certain  skills  and
services are offered by talent concentrated in countries with higher risks of instability and geopolitical uncertainty, such as Russia and Ukraine,

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both of which have experienced recent political unrest and are facing potential military conflict, which may interfere with the talent’s ability to access our work marketplace and for us
to support users in such countries. In addition, we engage talent located in many countries to provide services for our managed services offering and to us for internal projects.
Because our website is generally accessible by users worldwide, we have received in the past, and may continue to receive, notices from jurisdictions claiming that we or our users
are  required  to  comply  with  their  laws.  Laws  outside  of  the  United  States  regulating  the  internet,  payments,  escrow,  data  protection,  data  residency,  privacy,  taxation,  terms  of
service, website accessibility, consumer protection, intellectual property ownership, services intermediaries, payment intermediaries, labor and employment, wage and hour, worker
classification, worker health, background checks, and recruiting and staffing companies, among others, which could be interpreted to apply to us, are often less favorable to us than
those in the United States, giving greater rights to competitors, users, and other third parties. Compliance with international laws and regulations may be more costly than expected,
may require us to change our business practices or restrict or modify our offerings, and the imposition of any such laws or regulations on us, our users, or third parties that we or our
users utilize to provide or use our services, may adversely impact our revenue and business. In addition, we may be subject to multiple overlapping legal or regulatory regimes that
impose  conflicting  requirements  which  could  lead  to  additional  compliance  costs  and  enhanced  legal  risks.  Moreover,  all  of  these  risks  will  be  exacerbated  as  we  expand  our
operations internationally, including extending our physical presence and registering to do business outside the United States or investing in localization efforts.

Risks  inherent  in  conducting  business  with  an  international  user  base,  engaging  talent  globally,  localizing  our  work  marketplace,  and  expanding  our  operations  internationally
include, but are not limited to:

•

•

•

•

•

•

•

•

•

•

•

being deemed to conduct business or have operations in the jurisdictions where users, including talent that provide services to us, are resident and being subject to their
laws and regulatory requirements;

new, changed, or conflicting regulatory requirements;

varying worker classification standards, regulations, and approaches to enforcement and requirements and expectations of employment;

compliance with U.S. and foreign laws designed to combat money laundering and the financing of terrorist activities;

the imposition of taxes on transactions between us and our users or among our users, or the imposition of liability on us for the failure to collect and remit taxes owed by our
users;

compliance  with  U.S.  and  foreign  laws  and  regulations  regarding  privacy,  data  protection,  information  security,  and  the  collection,  storing,  retention,  sharing,  use,
processing, transfer, disclosure, and protection of personal information and other content;

the cost and burden of complying with a wide variety of laws that may be deemed to apply to us, including those relating to labor and employment matters (including but not
limited to requirements with respect to works councils or similar labor organizations, worker classification, and taxation on income or earnings, including the obligation to
withhold and remit taxes), payments, consumer and data protection, privacy, network security, encryption, data residency, and taxes, as well as securing expertise in local
law and related practices;

costs of localizing services, including adding the ability for clients to pay in local currencies;

tariffs,  export  and  import  restrictions,  restrictions  on  foreign  investments,  sanctions,  changes  to  existing  trade  arrangements  between  various  countries,  and  other  trade
barriers or protection measures, including those affecting certain countries with higher risks of instability and geopolitical uncertainty, such as Russia and Ukraine;

geopolitical instability and security risks, such as armed conflict and civil or military unrest, political instability, human rights concerns, and terrorist activity in countries where
we have users, such as the geopolitical uncertainty in Russia and Ukraine;

retaliatory actions by foreign governments intended to disrupt business like ours in the United States as a result of new or increased sanctions or export controls;

• macroeconomic and political conditions, including in certain foreign jurisdictions such as the evolving relations between the United States and China;

•

regional or global public health crises, such as the COVID-19 pandemic;

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•

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difficulties in, and costs of, staffing, managing, and operating international operations or support functions;

economic weakness or currency-related challenges or crises;

fluctuations in foreign currency exchange rates;

lack of acceptance of localized services or of services generally because they are not localized;

private, corporate or state-sponsored espionage, ransomware, or cyberterrorism;

• weaker intellectual property protection;

•

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organizing or similar activity by workers, local unions, works councils, or other labor organizations in the U.S. or elsewhere; and

our ability to adapt to business practices and client requirements in different cultures.

The risks described above may also make it costly or difficult for us to expand our operations internationally. Analysis of, and compliance with, foreign laws and regulations may
substantially increase our cost of doing business. We may be unable to keep current with changes in laws and regulations as they develop. Although we have implemented policies
and procedures designed to analyze whether these laws apply and, if applicable, support compliance with these laws and regulations, there can be no assurance that we will always
maintain compliance, that our interpretations are or will remain correct, or that all of our employees, contractors, partners, users, and agents will comply. Any violations could result
in  enforcement  actions  or  other  proceedings,  fines,  civil  and  criminal  penalties,  damages,  interest,  costs  and  fees  (including  but  not  limited  to  legal  fees),  injunctions,  loss  of
intellectual  property  rights,  or  reputational  harm.  If  we  are  unable  to  comply  with  these  laws  and  regulations  or  manage  the  complexity  of  global  operations  and  support  an
international user base successfully and in a cost-effective manner, our business, operating results, and financial condition could be adversely affected.

There may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is challenged.

Clients  are  generally  responsible  for  properly  classifying  the  talent  they  engage  through  our  work  marketplace  under  our  terms  of  service.  Some  clients  opt  to  classify  talent  as
employees for certain work, while talent in many other cases are classified as independent contractors.

We  offer  an  optional  service  to  users  of  our  Upwork  Enterprise  offering  and  other  premium  offerings,  through  which  we  help  classify  talent  as  employees  of  third-party  staffing
providers  or  independent  contractors.  For  clients  of  these  services,  subject  to  applicable  law  and  the  terms  of  our  agreement  with  the  client,  we  indemnify  clients  from
misclassification risk and make warranties to the client, such as to compliance with applicable laws. In addition, we offer a number of other premium offerings where we provide
increased  assistance  to  users  to  find  and  contract  with  one  another,  which  could  increase  employment-related  risks.  Third-party  staffing  providers  employ  talent  classified  as
employees for clients, and failure of these staffing providers to comply with all legal and tax requirements could adversely affect our business. Moreover, material business changes
by one or more of our third-party staffing providers could negatively impact our business and financial results, including increased costs for clients or us, a reduced profit margin, a
diminished user experience, or the inability to offer the staffing provider services in one or more jurisdictions. We also use our work marketplace to find, classify, and engage talent
to  provide  services  for  us  and  for  our  managed  services  offering.  In  general,  any  time  a  court  or  administrative  agency  determines  that  we  or  our  clients  that  use  our  work
marketplace have misclassified talent as an independent contractor, we or our users could incur tax and other liabilities for failing to properly withhold or pay taxes on the talent’s
compensation as well as potential wage and hour and other liabilities depending on the circumstances and jurisdiction. We have in the past been, and may in the future be, subject
to administrative inquiries and audits concerning the taxation and classification of our workers and the users of our work marketplace. Certain claims may not be covered by our
insurance,  and  we  cannot  be  certain  that  any  insurance  coverage  that  we  have  or  may  obtain  will  extend  to  or  be  adequate  for  liabilities  actually  incurred  or  that  insurance  will
continue to be available to us on economically reasonable terms, or at all.

There is often uncertainty in the application of worker classification laws, and consequently there is risk to us and to users, both talent and clients, that independent contractors
could be deemed to be misclassified under applicable law. The tests governing whether a service provider is an independent contractor or an employee are typically highly fact
sensitive and vary by governing law. Laws and regulations that govern the status and misclassification of independent contractors are also subject to change as well as to divergent
interpretations by various authorities, which can create uncertainty and unpredictability. For example, in California, Assembly Bill 5, which we refer to as AB 5, went into effect on
January 1, 2020 and has the stated purpose of codifying the 2018 state supreme court

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decision in Dynamex Operations West, Inc. v. Superior Court of Los Angeles. Together, they retroactively change the standard in California for determining worker classification and
are widely viewed as expanding the scope of the definition of “employee” for most purposes under California law. Since the enactment of AB 5, and subsequent amendments and
challenges (including California’s Proposition 22) to the law, there is little guidance from the courts or the regulatory authorities charged with its enforcement and there remains a
degree of uncertainty regarding its application.

A misclassification determination, allegation, claim, or audit creates potential exposure for users and for us, including but not limited to reputational harm and monetary exposure
arising from or relating to failure to withhold and remit taxes, unpaid wages, and wage and hour laws and requirements (such as those pertaining to minimum wage and overtime);
claims for employee benefits, social security contributions, and workers’ compensation and unemployment insurance; claims of discrimination, harassment, and retaliation under
civil  rights  laws;  claims  under  laws  pertaining  to  unionizing,  collective  bargaining,  and  other  concerted  activity;  and  other  claims,  charges,  or  other  proceedings  under  laws  and
regulations applicable to employers and employees, including risks relating to allegations of joint employer liability. Such claims could result in monetary damages (including but not
limited to wage-based damages or restitution, compensatory damages, liquidated damages, and punitive damages), interest, fines, penalties, costs, fees (including but not limited to
attorneys’ fees), criminal and other liability, assessment, injunctive relief, or settlement. For example, particularly around the onset of the COVID-19 pandemic, these types of claims
were  more  frequent  in  light  of  then-deteriorating  macroeconomic  conditions,  more  prone  to  agency  error  in  light  of  overwhelmed  agencies,  more  commonly  submitted  on  a
fraudulent basis, and more difficult to successfully oppose or appeal due to COVID-19 related delays, and such events may increase in frequency again if similar circumstances
recur. Claims naming our company became, and may again become, prevalent in light of legislative and regulatory responses to the COVID-19 pandemic. These claims may also
become  more  frequent  as  our  brand  awareness  increases.  Such  a  claim,  allegation,  or  adverse  determination,  including  but  not  limited  to  with  respect  to  the  talent  that  provide
services to us, or the requirement for us to indemnify a client, could also harm our brand and reputation, which could adversely impact our business. While these risks are mitigated,
in part, by our contractual rights of indemnification against third-party claims, any limitations or obligations that we include in our contracts with clients to limit our exposure to claims
could be determined to be unenforceable, could be costly to enforce or ineffective, or may otherwise prove inadequate.

The regulatory landscape regarding contractor classification is rapidly changing, and changes in these laws could adversely affect demand for our services and work
marketplace and adversely affect our business.

Worker classification and independent contractor issues, including AB 5, have been the subject of widespread debate both in the United States and abroad. It is possible that other
jurisdictions,  including  the  U.S.  federal  government,  U.S.  states,  such  as  New  York,  Washington,  and  Illinois,  and  jurisdictions  outside  the  United  States,  such  as  the  United
Kingdom and the EU through its work on the Platform Workers Directive and other legislative and regulatory instruments, may change their definition of “employment” to include
arrangements currently viewed as independent. Additionally, changes to laws and regulation may be subject to challenge in court (e.g. AB 5, which had a retroactive effect, and
California’s Proposition 22, which was recently ruled unconstitutional). Likewise, the EU, the United Kingdom, and other jurisdictions are exploring changes to worker classification
through a variety of legal instruments, such as the Digital Services Act and Digital Markets Act in the EU. These new and changing laws could alter the legislative and regulatory
landscape  regarding  how  governments  may  choose  to  regulate  independent  contractors  broadly  and  in  specific  sectors.  These  changes  may  affect  how  our  users  run  their
businesses. As a result, there is significant uncertainty regarding the worker classification regulatory landscape and what it will look like in future years, and compliance with any
new legislation or regulations may be costly and difficult or they may be impossible to comply with in a commercially reasonable manner. In addition, any developments or changes
in  the  regulatory  environment  impacting  worker  classification  and  independent  contractors  may  reduce  the  demand  for  independent  contractors  more  generally  in  one  or  more
jurisdictions and have an adverse effect on our business, operating results, and financial condition.

Changes in laws or regulations relating to privacy or the protection, collection, storage, processing, transfer, or use of personal information, or any actual or perceived
failure by us to comply with such laws and regulations or our privacy policies, could adversely affect our business.

We  receive,  collect,  store,  process,  transfer,  and  use  personal  information  and  other  user  data.  There  are  numerous  federal,  state,  local,  and  international  laws  and  regulations
regarding privacy, data protection, information security, and the collection, storing, sharing, use, processing, transfer, disclosure, and protection of personal information and other
data. The scope of these laws and regulations is changing, subject to differing interpretations, and may be inconsistent among states and countries, or conflict with other laws and
regulations. We are also subject to the

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terms of our privacy policies and legal and contractual obligations to third parties related to privacy, data protection, and information security. The regulatory framework for privacy
and data protection worldwide is, and is likely to remain for the foreseeable future, uncertain and complex, and it is possible that these or other actual or alleged obligations may be
interpreted and applied in a manner that we do not anticipate or that is inconsistent from one jurisdiction to another and may conflict with other rules or our practices. Further, any
significant  change  to  applicable  laws,  regulations,  or  industry  practices  regarding  the  collection,  use,  retention,  security,  or  disclosure  of  the  data  of  our  users,  employees,
contractors, or others, or their interpretation or enforcement, or any changes regarding the manner in which the express or implied consent of users for the collection, use, retention,
or disclosure of such data must be obtained, including in response to the COVID-19 pandemic, could increase our costs and require us to modify our services and features, possibly
in a material manner, which we may be unable to complete in a cost-effective manner, or at all, and may limit our ability to store and process user data or develop new services and
features.

We  also  expect  that  there  will  continue  to  be  new  laws,  regulations,  and  industry  standards  concerning  privacy,  data  protection,  and  information  security  that  are  proposed  and
enacted  in  various  jurisdictions.  For  example,  Europe’s  General  Data  Protection  Regulation,  which  we  refer  to  as  the  GDPR,  and  the  U.K.  General  Data  Protection  Regulation
(which implements the GDPR into U.K. law), impose stringent data protection requirements and provide for significant penalties for noncompliance. Additionally, California enacted
legislation,  the  California  Consumer  Privacy  Act,  which  we  refer  to  as  the  CCPA.  The  CCPA  requires,  among  other  things,  covered  companies  to  provide  new  disclosures  to
California consumers and allows such consumers new abilities to opt-out of certain sales of personal data. The CCPA also provides for civil penalties for violations as well as a
private right of action for data breaches that may increase data breach litigation. Further, the California Privacy Rights Act, which was passed in November 2020 and is fully effective
in January 2023, significantly modifies the CCPA. These modifications will require us to incur additional costs and expenses in our effort to comply. Virginia and Colorado recently
enacted similar data privacy legislation that will take effect in 2023, and several other states and countries are considering expanding or passing privacy laws in the near term. The
enactment of more restrictive laws, rules, regulations, or future enforcement actions or investigations could impact us through increased costs or restrictions on our business, and
noncompliance could result in regulatory penalties and significant legal liability. Furthermore, the costs of compliance with, and other burdens imposed by, the laws, regulations, and
policies that are applicable to the businesses of our users may limit the adoption and use of, and reduce the overall demand for, our work marketplace.

Additionally, if third parties we work with violate applicable laws, regulations, or agreements, such violations may put the data of our users, employees, contractors, and others at
risk, could result in governmental investigations or enforcement actions, fines, litigation, claims, or public statements against us by consumer advocacy groups or others, and could
result in significant liability, cause our users to lose trust in us, and otherwise have an adverse effect on our reputation and business. Further, public scrutiny of or complaints about
technology companies or their data handling or data protection practices, even if unrelated to our business, industry, or operations, may lead to increased scrutiny of technology
companies,  including  us,  and  may  cause  government  agencies  to  enact  additional  regulatory  requirements,  or  to  modify  their  enforcement  or  investigation  activities,  which  may
disrupt the conduct of our business, increase our liability, increase our costs and risks, and adversely affect our business.

We may be subject to escrow, payment services, and money transmitter regulations that may adversely affect our business.

Our  subsidiary,  Upwork  Escrow,  is  licensed  as  an  internet  escrow  agent  under  California’s  Escrow  Law  and  is  subject  to  regulations  applicable  to  internet  escrow  agents
promulgated  by  the  DFPI.  While  we  have  received  two  inquiries,  each  prior  to  2014,  from  regulatory  authorities  inquiring  whether  we  are  engaging  in  payment  activities,  these
inquiries were resolved in our favor and did not require us to obtain a license in the applicable jurisdiction.

Although we are a licensed internet escrow agent and we believe that our operations comply with existing U.S. federal, state, and international laws and regulatory requirements
related to escrow, money transmission, and the handling or moving of money, the laws or regulations may change, interpretations of existing laws and regulations may also change,
and  our  operations  and  offerings  may  change  resulting  in  new  or  different  regulatory  requirements  being  applicable  to  or  preferable  for  our  business.  As  a  result,  we  could  be
required, or choose, to become licensed as an escrow agent or a money transmitter (or other similar licensee) in other U.S. states or other jurisdictions or as a money services
business under federal laws and regulations or similar licenses under the laws and regulations of other jurisdictions. It is also possible that we could become subject to regulatory
enforcement or other proceedings in those states or other jurisdictions with escrow, money transmission, or other similar statutes or regulatory requirements related to the handling
or moving of money, and such risk may increase if we are required or choose to pursue additional or different licenses, which could in turn have a significant impact on our business,
even if we

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voluntarily  sought  the  licenses  or  were  to  ultimately  prevail  in  such  proceedings.  We  may  also  be  required,  or  choose,  to  become  licensed  as  a  payment  institution  (or  obtain  a
similar license) under the European Payment Services Directive or other international laws and regulations or may choose to obtain such a license even if not required or in order to
support  new  products  or  services.  Any  developments  or  inconsistencies  in  the  requirements,  interpretations  or  applicability  of  the  laws  or  regulations  related  to  escrow,  money
transmission, or the handling or moving of money; material changes to the mandate, purview or regulatory approach at the DFPI; or increased scrutiny of our business may lead to
additional compliance costs and administrative overhead.

The application of laws and regulations related to escrow, money transmission, and the handling or moving of money is subject to significant complexity and uncertainty, particularly
as those laws relate to new and evolving business models. If we fail to comply with one or more escrow or money transmitter or other similar statutes or regulatory requirements
related to the handling or moving of money in any U.S. state or other jurisdiction, we may be subject to the imposition of fines or restrictions on our business, our ability to offer some
or  all  of  our  services  in  the  relevant  jurisdiction  may  be  limited  or  suspended,  and  we  may  be  subject  to  civil  or  criminal  liability  and  our  business,  operating  results,  financial
condition, reputation, and brand could be adversely affected.

Failure to comply with anti-corruption, anti-money laundering, and sanctions laws, and similar laws associated with our activities outside of the United States, could
subject us to penalties and other adverse consequences.

We have voluntarily implemented an anti-money laundering compliance program designed to address the risk of our work marketplace being used to facilitate money laundering,
terrorist financing, or other illegal activity. Our program may not be sufficient to prevent our work marketplace from being used to improperly move money or may be found not to
satisfy the expectations of our partners or regulators. In addition, if we or a regulator determines that we are required to comply with the Bank Secrecy Act (BSA), 31 U.S.C. § 5311,
or  similar  laws  outside  of  the  United  States,  we  may  be  required  to  enhance  or  alter  our  anti-money  laundering  compliance  program.  We  also  have  policies,  procedures,  and
technology designed to allow us to comply with U.S. economic sanctions laws and prevent our work marketplace from being used to facilitate business in countries, regions, or with
persons or entities included on designated lists promulgated by the U.S. Department of the Treasury’s Office of Foreign Assets Control, which we refer to as OFAC, and equivalent
foreign authorities. Our efforts to comply with OFAC regulations may not be effective, including in preventing users from using our services within the OFAC-sanctioned countries
and regions, our partners or regulators may determine they are insufficient, or we may be required to comply with new sanctions laws and regulations, which may require us to
further revise or expand our compliance program. For example, geopolitical events, such as recent tensions and possible military conflict between Ukraine and Russia or tensions
between Russia and the United States or other countries, may result in new sanctions negatively affecting our users and business. Given the technical limitations in developing
controls to prevent, among other things, the ability of users to publish on our work marketplace false or deliberately misleading information or to develop sanctions-evasion methods,
it is possible that we may inadvertently and without our knowledge provide services to individuals or entities that have been designated by OFAC or are located in a country subject
to an embargo by the United States that may not be in compliance with the economic sanctions regulations administered by OFAC.

Consequences for failing to comply with applicable anti-money laundering and sanctions laws and regulations, even unintentional violations, could include fines, criminal and civil
lawsuits, forfeiture of significant assets, or other enforcement actions. We could also be required to make costly and burdensome changes to our business practices or compliance
programs as a result of regulatory scrutiny, voluntary changes we may make to our business strategy, or the expansion of our operations internationally, including expanding our
presence outside the United States. In addition, any perceived or actual breach of compliance by us, our users, or payment partners with respect to applicable laws, rules, and
regulations  could  have  a  significant  impact  on  our  reputation  and  could  cause  us  to  lose  existing  users,  prevent  us  from  obtaining  new  users,  cause  other  payment  partners  to
terminate or not renew their agreements with us, negatively impact investor sentiment about our company, require us to expend significant funds to remedy problems caused by
violations and to avert further violations, and expose us to legal risk and potential liability, all of which may adversely affect our business, operating results, and financial condition
and may cause the price of our common stock to decline.

For example, our and other freelancing platforms and websites have been the subject of additional scrutiny and press attention relating to North Korea. A State Department advisory
issued in July 2018 stated that “there are cases where North Korean companies exploit the anonymity provided by freelancing websites to sell their IT services to unwitting buyers.”
Additionally, press reports have stated that North Korean operatives have used various social media applications and freelancing websites, including ours. Accordingly, although we
have controls in place to detect and prevent such OFAC violations and our systems show no access from persons in North Korea,

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nor from any other OFAC-sanctioned jurisdictions, we may face higher levels of scrutiny by users, partners, and regulators due to the publishing of this advisory and those or similar
press reports.

We are also subject to the U.S. Foreign Corrupt Practices Act, which we refer to as the FCPA, the U.S. domestic bribery statute contained in 18 U.S.C. § 201, the U.S. Travel Act,
and the UK Bribery Act 2010, and may be subject to other anti-bribery laws in countries in which we conduct activities or have users. We face significant risks if we fail to comply
with the FCPA and other anti-corruption laws. In many foreign countries, particularly in countries with developing economies, it may be a local custom that businesses engage in
practices that are prohibited by the FCPA or other applicable laws and regulations. We may have direct or indirect interactions with officials and employees of government agencies
or  state-owned  or  affiliated  entities,  and  we  may  be  held  liable  for  the  corrupt  or  other  illegal  activities  of  these  third-party  intermediaries,  our  employees,  representatives,
contractors, partners, and agents, even if we prohibit or do not explicitly authorize such activities. We have implemented an anti-corruption compliance policy, but we cannot ensure
that all of our employees, users, and agents, as well as those contractors to which we outsource certain of our business operations, will not take actions in violation of our policies or
agreements and applicable law, for which we may be ultimately held responsible.

Any violation of the FCPA, other applicable anti-corruption laws, or other anti-bribery, anti-money laundering, or sanctions laws, could result in investigations and actions by federal
or state attorneys general or foreign regulators, loss of export privileges, severe criminal or civil fines and penalties or other sanctions, forfeiture of significant assets, whistleblower
complaints,  and  adverse  media  coverage,  which  could  have  an  adverse  effect  on  our  reputation,  business,  operating  results,  and  prospects.  In  addition,  responding  to  any
enforcement  action  may  result  in  a  significant  diversion  of  management’s  attention  and  resources  and  significant  defense  costs  and  other  professional  fees.  Further,  even  if  we
maintain  proper  controls  and  remain  in  compliance  with  applicable  anti-corruption,  anti-money  laundering,  and  sanctions  laws  or  regulations,  should  any  of  our  competitors  not
implement sufficient controls and be found to have violated such laws or regulations, user perception of online freelance marketplaces in general may decrease and our business,
brand, and reputation may be adversely affected.

We may be required to comply with governmental export control laws and regulations. Our failure to comply with these laws and regulations could have an adverse
effect on our business and operating results.

We may be subject to export controls and other sanctions regulations that prohibit the shipment or provision of certain products and services to certain countries, governments, and
persons, and new export controls and sanctions are promulgated from time to time. For example, geopolitical events, such as recent tensions and possible military conflict between
Ukraine and Russia or tensions between Russia and the United States or other countries, may result in new sanctions or export controls affecting our users and business. While we
take precautions to prevent aspects of our work marketplace from being exported in violation of these laws, including implementing internet protocol address blocking, we cannot
guarantee that the precautions we take will prevent violations of export control and sanctions laws. If we are found to be in violation of U.S. sanctions or export control laws, it could
result in substantial fines and penalties for us and for the persons working for us.

In addition, various countries regulate the import and export of certain encryption and other technology, including imposing import and export permitting and licensing requirements,
and have enacted laws that could limit our ability to distribute aspects of our work marketplace or could limit our users’ ability to access our work marketplace in those countries.
Changes in our work marketplace, or future changes in export and import regulations may prevent our international users from utilizing our work marketplace or, in some cases,
prevent the export or import of our work marketplace to certain countries, governments, or persons altogether. Any change in export or import regulations, economic sanctions or
related  legislation,  or  change  in  the  countries,  governments,  persons,  or  technologies  targeted  by  such  regulations,  could  result  in  decreased  use  of  our  work  marketplace  by
existing or potential users with international operations. Any decreased use of our work marketplace or limitation on our ability to export or sell our products would likely adversely
affect our business, operating results, and financial results.

We are vulnerable to intellectual property infringement claims and challenges to our intellectual property rights brought against us by third parties.

We  operate  in  a  highly  competitive  industry,  and  there  has  been  considerable  activity  in  our  industry  to  develop  and  enforce  intellectual  property  rights.  Intellectual  property
infringement claims against us or our users or third-party partners could result in monetary liability or a material disruption in the conduct of our business. We cannot be certain that
aspects of our work marketplace, content, and brand names do not or will not infringe valid patents, trademarks, copyrights, or other intellectual property rights held by third parties,
including our competitors. Also, we are now, have in the past been, and may in the future be, subject to legal proceedings and claims relating to the intellectual property of others,
including our competitors, in the ordinary course of our business. The likelihood of

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intellectual  property-related  litigation  and  disputes  may  increase  due  to  the  increased  attention  on  our  market  segment  due  to  the  ongoing  shift  to  remote  work.  Companies,
including  non-practicing  entities  and  our  competitors,  have  also  sent  us  demand  letters  and  instituted  proceedings  alleging  that  we  infringe  their  intellectual  property,  seeking
licensing fees, royalties and damages, and demanding that we cease certain commercial activity. We may receive such demand letters and be subject to similar proceedings in the
future. Our competitors and other third parties have in the past challenged, and may in the future challenge, our registration or use of our trademarks, including “Upwork,” and other
intellectual property rights, and such a challenge, even if not successful, could adversely affect our brand and business. Our competitors and others may now and in the future have
significantly larger and more mature patent portfolios than we have or trademarks or other rights that pre-date and take precedence over our own. We may also be obligated to
indemnify certain clients on our work marketplace or strategic partners or others in connection with such infringement claims, or to obtain licenses from third parties or modify our
work  marketplace  or  marketing  strategy,  and  each  such  obligation  would  require  us  to  expend  additional  resources  and  could  divert  the  attention  of  management.  Some  of  our
infringement indemnification obligations related to intellectual property are contractually capped at a very high amount or not capped at all.

Any  litigation  or  other  disputes  relating  to  allegations  of  intellectual  property  infringement  could  subject  us  to  significant  legal  costs  and  liability  for  damages,  invalidate  our
proprietary rights, or force us to do one or more of the following:

•

•

•

•

•

•

•

cease conducting certain operations in some or all jurisdictions, or stop using technology that contains the allegedly infringing intellectual property;

stop using the name “Upwork” or other trademarks in some or all jurisdictions;

incur significant legal expenses;

pay substantial damages or ongoing royalty payments to the party whose intellectual property rights we may be found to be infringing;

pay substantial amounts in settlement to a party that asserts allegations of intellectual property infringement;

prevent us from offering aspects of our work marketplace or make expensive and disruptive changes to our work marketplace or our methods of doing business; or

attempt to obtain a license to the relevant intellectual property from third parties, which may not be available on reasonable terms or at all.

Even if intellectual property claims do not result in litigation or are resolved in our favor, these claims, and the time and resources necessary to resolve them, could divert resources
and  the  attention  of  management  and  adversely  affect  our  business  and  operating  results.  We  expect  that  the  occurrence  of  infringement  claims  is  likely  to  grow  as  the  market
segment for independent talent and the clients that engage them grows. Accordingly, our exposure to damages resulting from infringement claims could increase and this could
require us to expend additional financial and management resources.

Failure to protect our intellectual property could adversely affect our business.

Our  success  depends  in  large  part  on  our  proprietary  technology  and  data.  We  rely  on  various  intellectual  property  rights,  including  patents,  copyrights,  trademarks,  and  trade
secrets, as well as confidentiality provisions and contractual arrangements, to protect our proprietary rights. In addition, to protect our brand, we also expend substantial resources
to  register  and  defend  our  trademarks  and  to  prevent  others  from  using  the  same  or  substantially  similar  marks.  As  the  adoption  of  remote  work  becomes  more  prevalent  and
competitors enter our market segment, our exposure to unauthorized copying and use of our work marketplace, technology, intellectual property, and other proprietary information
may increase. If we do not protect and enforce our intellectual property rights successfully or cost-effectively, our competitive position may suffer, which would adversely impact our
operating results.

Our  pending  and  future  patent  or  trademark  applications  may  not  be  approved,  or  competitors  or  others  may  challenge  the  validity,  enforceability,  or  scope  of  our  patents,  the
registrability  or  validity  of  our  trademarks,  or  the  trade  secret  status  of  our  proprietary  information.  If  we  are  unsuccessful  in  a  dispute  or  litigation,  we  may  be  unable  to  stop
competitors or others from using our marks or confusingly similar marks, and we may suffer dilution, loss of reputation, genericization, or other harm to our brand. Efforts to protect
and  enforce  our  intellectual  property  rights,  even  if  successful,  may  be  costly,  negatively  impact  our  brand,  negatively  affect  worker  productivity,  and  be  time  consuming  and
distracting to our management. There can be no assurance that additional patents or trademarks

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will be issued or that any patents or trademarks that are issued will provide significant protection for our intellectual property. In addition, our patents, copyrights, trademarks, trade
secrets,  and  other  intellectual  property  rights  may  not  provide  us  a  significant  competitive  advantage.  There  is  no  assurance  that  the  particular  forms  of  intellectual  property
protection  that  we  seek,  including  business  decisions  about  when  and  where  to  file  patents  or  register  or  renew  trademarks  and  when  and  how  to  maintain  and  protect  trade
secrets, will be adequate to protect our business, or that common law protection will be sufficient for marks or in jurisdictions where we do not register the marks.

We may not pursue or file patent applications or apply for registration of copyrights or trademarks in the United States and foreign jurisdictions in which we have a presence with
respect to our potentially patentable inventions, works of authorship, and marks and logos for a variety of reasons, including the cost of procuring such rights and the uncertainty
involved in obtaining adequate protection from such applications and registrations. Moreover, recent amendments to, developing jurisprudence regarding, and possible changes to
intellectual property laws and regulations, including U.S. and foreign patent law, may affect our ability to protect and enforce our intellectual property rights or defend against claims
alleging we are infringing others’ rights. If the intellectual property rights that we develop are not sufficient to protect our proprietary technology and data, our brand, our business,
financial condition and operating results could be adversely affected.

In addition, the laws of some countries do not provide the same level of protection for our intellectual property as do the laws of the United States. As our global reputation grows
and  we  expand  our  international  activities,  our  exposure  to  unauthorized  copying  and  use  of  our  work  marketplace  and  proprietary  information  will  likely  increase.  Despite  our
precautions,  our  intellectual  property  is  vulnerable  to  unauthorized  access  through  employee  or  third-party  error  or  actions,  theft,  cybersecurity  incidents,  and  other  security
breaches  and  incidents.  It  is  possible  for  third  parties  to  infringe  upon  or  misappropriate  our  intellectual  property,  to  copy  our  work  marketplace,  and  to  use  information  that  we
regard as proprietary to create products and services that compete with ours. Effective intellectual property protection may not be available to us in every country in which our work
marketplace  is  available.  In  addition,  many  countries  limit  the  enforceability  of  patents  or  other  intellectual  property  rights  against  certain  third  parties,  including  government
agencies or government contractors. In these countries, patents or other intellectual property rights may provide limited or no benefit. Further, certain countries impose additional
conditions on the transfer of intellectual property rights from individuals to companies, which may make it more difficult for us to secure and maintain intellectual property protection
in those countries. We may need to expend additional resources to defend our intellectual property rights domestically or internationally, which could be costly, time consuming, and
distracting to management and could impair our business or adversely affect our domestic or international expansion. If we cannot adequately protect and defend our intellectual
property, we may not remain competitive, and our business, operating results, and financial condition may be adversely affected.

We rely on trade secrets as an important aspect of our intellectual property program and to cover much of our technology and know-how. We seek to protect our trade secrets and
obtain  rights  in  intellectual  property  developed  by  service  providers  through  confidentiality  and  invention  assignment  or  intellectual  property  ownership  agreements  with  our
employees, contractors, and other parties. In addition, for employees of third-party staffing providers or other contractors, the employer agrees to enter into these agreements with
individual workers. We also take other measures to protect our information and data, including implementing acceptable use policies, limiting access to our information and data
through technological means, and monitoring and limiting the dissemination of our information and data outside of company-owned information systems. We cannot ensure that
these agreements, or all the terms thereof, will be enforceable or compliant with applicable law, or these agreements and other measures will be effective in controlling access to,
use  of,  and  distribution  of  our  proprietary  information  or  in  effectively  securing  and  maintaining  exclusive  ownership  of  intellectual  property  developed  by  our  current  or  former
employees  and  contractors.  Most  of  our  employees  and  all  of  the  contractors  with  which  we  work  are  remote,  which  may  make  it  more  difficult  to  control  use  of  confidential
materials, increasing the risk that our source code or other confidential or trade secret information may be exposed. Further, these agreements with our employees, contractors, and
other parties may not prevent other parties from independently developing technologies that are substantially equivalent or superior to our work marketplace. Any failure to protect
intellectual property that we develop or our proprietary technology and data would adversely affect our business, operating results, and financial condition.

We  spend  significant  time  and  resources  securing  and  monitoring  our  intellectual  property  rights,  and  we  may  or  may  not  be  able  to  detect  infringement  by  third  parties.  Our
competitive  position  may  be  adversely  impacted  if  our  efforts  to  secure  and  protect  our  intellectual  property  are  not  successful,  or  we  cannot  detect  infringement  or  enforce  our
intellectual  property  rights  quickly  or  at  all.  In  some  circumstances,  we  may  choose  not  to  pursue  enforcement  because  an  infringer  may  have  a  dominant  intellectual  property
position or for other business reasons. In addition, competitors might avoid infringement by designing around our intellectual property rights or by developing non-

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infringing  competing  technologies.  We  have  in  the  past  been,  and  may  in  the  future  be,  forced  to  rely  on  litigation,  opposition,  and  cancellation  actions,  and  other  claims  and
enforcement actions to protect our intellectual property, including to dispute registration, use of marks that may be confusingly similar to our own marks, or use of technologies that
infringe on our intellectual property. Similar claims and other litigation may be necessary in the future to enforce and protect our intellectual property rights. Litigation brought to
protect and enforce our intellectual property rights could be costly, time-consuming, and distracting to management, and could result in the impairment or loss of portions of our
intellectual property. Further, our efforts to enforce our intellectual property rights may be met with defenses; counterclaims attacking the scope, validity, and enforceability of our
intellectual property rights; or counterclaims and countersuits asserting infringement by us of third-party intellectual property rights. Our failure to secure, protect, and enforce our
intellectual property rights could adversely affect our brand and our business, and we could lose the right to use certain intellectual property or lose the opportunity to license our
technology to others or to collect royalty payments based upon successful protection and assertion of our intellectual property against others.

Our work marketplace contains open source software components, and failure to comply with the terms of the underlying licenses could restrict our ability to market or
operate our work marketplace.

Our work marketplace incorporates certain open source software. An open source license typically permits the use, modification, and distribution of software in source-code form
subject to certain conditions. Some open source licenses contain conditions that any person who distributes a modification or derivative work of software that was subject to an
open  source  license  make  the  modified  version  subject  to  the  same  open  source  license.  Distributing  software  that  is  subject  to  this  kind  of  open  source  license  can  lead  to  a
requirement that certain aspects of our work marketplace be distributed or made available in source code form. Although we do not believe that we have used open source software
in a manner that might condition its use on our distribution of any portion of our work marketplace in source code form, the interpretation of open source licenses is complex and,
despite our efforts, it is possible that we may be liable for copyright infringement, breach of contract, or other claims if our use of open source software is adjudged not to comply
with the applicable open source licenses.

Moreover, we cannot ensure that our processes for controlling our use of open source software in our work marketplace will be effective. If we have not complied with the terms of
an applicable open source software license, we may need to seek licenses from third parties to continue offering our work marketplace and the terms on which such licenses are
available may not be economically feasible, to re-engineer our work marketplace to remove or replace the open source software, to discontinue offering our work marketplace if re-
engineering could not be accomplished on a timely basis, to pay monetary damages, or to make available the source code for aspects of our proprietary technology, any of which
could adversely affect our business, operating results, and financial condition.

In addition to risks related to license requirements, use of open source software can involve greater risks than those associated with use of third-party commercial software, as open
source licensors generally do not provide warranties or assurances of title, performance, or non-infringement, nor do they control the origin of the software. There is typically no
support available for open source software, and we cannot ensure that the authors of such open source software will implement or push updates to address security risks or will not
abandon  further  development  and  maintenance.  Many  of  the  risks  associated  with  the  use  of  open  source  software,  such  as  the  lack  of  warranties  or  assurances  of  title  or
performance, cannot be eliminated, and could, if not properly addressed, negatively affect our business.

Litigation could have a material adverse impact on our operating results and financial condition.

From time to time, we are involved in litigation and make and receive demands and claims threatening possible litigation. The outcome of any litigation (including class actions and
individual  lawsuits  or  arbitration),  regardless  of  its  merits,  is  inherently  uncertain.  Regardless  of  the  merits  or  ultimate  outcome  of  any  claims  that  have  been  or  may  be  brought
against us or that we may bring against others, pending or future litigation could result in a diversion of management’s attention and resources and reputational harm, and we may
be required to incur significant expenses defending against these claims or pursuing claims against third parties. If we are unable to prevail in litigation, we could incur substantial
liabilities.  We  may  also  determine  that  the  most  cost-effective  and  efficient  way  to  resolve  a  dispute  is  to  enter  into  a  settlement  agreement,  and  terms  of  any  such  settlement
agreements are increasingly limited by legislation. Where we can make a reasonable estimate of the liability relating to pending litigation and determine that it is probable, we record
a related liability. As additional information becomes available, we assess the potential liability and revise estimates as appropriate. However, because of uncertainties relating to
litigation,  the  amount  of  our  estimates  could  be  wrong  as  determining  reserves  for  pending  litigation  is  a  complex,  fact-intensive  process  that  is  subject  to  judgment  calls.  Any
adverse determination related to litigation or adverse terms contained in a settlement agreement could require us to change our technology or our business practices in

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costly  ways,  prevent  us  from  offering  certain  offerings  or  services,  require  us  to  pay  monetary  damages,  fines,  or  penalties,  or  require  us  to  enter  into  royalty  or  licensing
arrangements, and could adversely affect our operating results and cash flows, harm our reputation, or otherwise negatively impact our business.

Risks Related to Finance, Accounting, and Tax Matters

We have a history of net losses, anticipate increasing our operating expenses in the future, and may not achieve or sustain profitability.

We have a history of incurring net losses, and we expect to incur net losses for the foreseeable future. For the years ended December 31, 2021 and 2020, we incurred net losses of
$56.2 million and $22.9 million, respectively. As of December 31, 2021, we had an accumulated deficit of $251.1 million. We have made, and expect to continue to make, significant
expenditures related to the development and expansion of our business, including investing in marketing programs and activities, such as brand promotion efforts, including those
designed  to  reach  new  and  existing  clients  seeking  to  engage  remote  talent  in  light  of  the  ongoing  shift  toward  remote  work;  expanding  our  sales  force;  enhancing  our  Upwork
Enterprise  and  other  premium  offerings;  expanding  our  services  and  features;  expanding  our  international  user  base;  localizing  our  offerings  in  select  locations;  broadening  and
deepening the categories on our work marketplace; promoting client engagement of the talent that typically optimize to deliver larger projects, including through our Upwork Payroll
offering; enhancing our mobile product offering and our U.S.-to-U.S. domestic marketplace offering; and in connection with legal, accounting, and other administrative expenses
related to operating as a public company. For example, in the fourth quarter of 2021, we increased our investment in brand marketing and to a lesser extent, our investment in sales
by expanding our sales team. These and other efforts may prove more expensive than we currently anticipate, and we may not succeed in increasing our revenue sufficiently, or at
all, to offset these higher expenses. While our revenue has grown in recent years, we may not be able to sustain the same level of growth in future periods, or at all. For example,
we experienced a reduction in the growth of GSV and revenue in the second quarter of 2020 due to the effects of the COVID-19 pandemic and could experience a similar reduction
in  GSV  and  revenue  growth  once  the  impact  of  the  COVID-19  pandemic  subsides  and  users  return  more  frequently  to  physical  offices  or  are  otherwise  no  longer  subject  to
restrictions related to the COVID-19 pandemic. If our revenue declines or fails to grow at a rate faster than increases in our operating expenses, we will not be able to achieve and
maintain profitability in future periods. As a result, we may continue to generate losses. We cannot ensure that we will achieve profitability in the future or that, if we do become
profitable, we will be able to sustain profitability.

Our operating results may fluctuate from quarter to quarter, which makes our future results difficult to predict.

Our quarterly operating results have fluctuated in the past and may fluctuate in the future, particularly during the macroeconomic uncertainty caused by the COVID-19 pandemic.
Additionally, we have a limited operating history under our current business strategy and pricing model, and we make pricing, product, and other changes from time to time, all of
which make it difficult to forecast our future results. As a result, you should not rely upon our past quarterly operating results as indicators of future performance. You should take
into  account  the  risks,  difficulties,  and  uncertainties  frequently  encountered  by  companies  in  highly  competitive  and  rapidly  evolving  markets.  Our  operating  results  in  any  given
quarter can be influenced by numerous factors, many of which are unpredictable or are outside of our control, including:

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uncertainty regarding demand for our work marketplace following the COVID-19 pandemic;

ongoing uncertainty and impact on the global economy and spending by large, medium, and small companies relating to the COVID-19 pandemic, the shift to remote work,
availability of qualified and in-demand talent, and uncertainty regarding the timing and nature of any future macroeconomic downturn, as discussed further below;

our ability to generate significant revenue from our Upwork Basic, Plus, and Enterprise offerings, and our other premium offerings, including newly introduced offerings;

due to our tiered pricing model for talent service fees, the mix in any period between talent that have billed larger amounts to clients on our work marketplace, where we
charge a lower rate on billings, and talent that have billed clients less on our work marketplace, where we charge a higher rate on billings;

our ability to maintain and grow our community of users, including our ability to acquire large enterprise and other clients with larger, longer-term independent talent needs
and qualified and in-demand talent;

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our ability to attract and retain talent that provide the types and quality of services sought by clients on our work marketplace, particularly talent that provide services for
which client demand exceeds supply on our work marketplace, or, in geographic regions in which clients are seeking to engage remote talent;

the demand for and types and quality of skills and services that are offered on our work marketplace by talent;

spending  patterns  of  clients,  including  whether  those  clients  that  use  our  work  marketplace  frequently  or  for  larger  projects,  reduce  their  spend,  stop  using  our  work
marketplace,  or  change  their  method  of  payment  to  us,  including  in  each  case  as  a  result  of  the  implementation  of  macroeconomic  or  other  external  factors  such  as
increased  competition,  pricing  changes,  or  the  introduction  of  new  or  modified  offerings  or  services  on  our  work  marketplace,  such  as  changes  made  in  the  pricing  and
packaging of Connects;

our ability to respond to competitive developments, including new and emerging competitors, pricing changes, and the introduction of new products and services by our
competitors;

the success of our marketing and brand positioning efforts;

the productivity and effectiveness of our sales force, including our ability to hire and adequately train qualified sales personnel;

the length and complexity of our sales cycles;

our ability to generate a profit and significant revenue from new offerings and services;

our ability to introduce new offerings and services or enhance existing offerings and services without adversely affecting our existing revenue;

the impact of consolidating or terminating existing offerings and services;

fluctuations in gross margin and revenue as a result of increased use of our managed services offering due to our recognition of the entire GSV from our managed services
offering as revenue, including the amounts paid to talent;

our ability to attract, retain, and grow small- and medium-sized business clients;

ongoing uncertainty regarding U.S. and global political conditions, including military conflicts in geographic locations where a portion of our remote workforce and a large
number of our users reside;

the number of users circumventing our work marketplace and our fees, which could increase during macroeconomic downturns;

the disbursement methods chosen by talent and changes in the mix of disbursement methods offered;

changes to our offerings and pricing model, including associated fees, and any resulting change in our ability to generate revenue, such as the pricing and packaging of
Connects purchases, how we recognize revenue, or changes in user behavior in response to such changes;

fluctuations in the prices that talent charge clients on our work marketplace, including as a result of a rise in inflation, which may impact the amount of revenue we recognize
as a percentage of GSV due to our tiered pricing model for talent service fees;

ransomware, data security, or privacy breaches or incidents and associated remediation costs and reputational harm;

spending patterns and project bidding behavior of talent with respect to the offerings and services available to them on our work marketplace, such as membership fees and
Connects purchases;

revenue recognition fluctuations for arrangements subject to our tiered pricing model for talent service fees;

litigation, regulatory investigations or enforcement actions, and adverse judgments, settlements, or other litigation-related costs;

seasonal spending patterns by clients or work patterns by talent, seasonality in the labor market, exaggerated impact of typical seasonality in the labor market (for example,
extended vacations during the summer and holiday seasons) as the COVID-19 pandemic subsides and the resulting relaxation or lifting of restrictions intended to prevent its
spread as well as the number of business days, the number of Mondays (i.e., the day we have the contractual right to bill and recognize revenue for a substantial portion of
our client fees each week) or the number of Sundays (i.e., the day we have the contractual right to bill and

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recognize revenue for the majority of our talent service fees each week) in any given quarter, as well as local, national, or international holidays;

any impairment charges on our operating lease asset and related leasehold improvements being recognized as a general and administrative expense due to a reduction to
our office space and our potential sublease of such office space at a rental rate that is less than our rent expense for such office space, or any termination fees we may
incur as a result of our termination of the operating lease for such office space. For example, as a result of our shift to a flexible work model for our workforce, in 2021 we
subleased  the  entirety  our  former  headquarters  in  Santa  Clara,  California  and  a  portion  of  our  current  headquarters  in  San  Francisco,  California,  and,  as  a  result,  we
incurred impairment charges of $8.7 million;

increases in, and timing of, operating expenses that we may incur to grow and expand our operations and to remain competitive, such as advertising and other marketing
expenses, including those associated with evolving our brand positioning and as we seek to grow our international user base;

the impact of sales, use, and other tax laws and regulations in jurisdictions in which we have users, including the requirement in certain jurisdictions to collect indirect taxes
on  user  fees,  to  withhold  and  remit  taxes  related  to  income  or  earnings,  or  to  pay  any  such  taxes  or  resulting  penalties  as  a  result  of  our  failure  to  comply  with  such
requirements;

changes in the mix of products and services that our enterprise clients or other users demand;

potential costs to attract, onboard, retain, and motivate qualified personnel to perform services for us;

changes in the law, application of the law (including as a result of changes in our services or offerings), or interpretation of law, or in the statutory, legislative, or regulatory
environment, such as with respect to privacy, data security, wage and hour regulations, worker classification (including classification of independent contractors or similar
workers and classification of employees as exempt or non-exempt), internet regulation, payments, payment processing, global trade, or tax obligations;

fluctuations in the mix of payment provider costs and the revenue generated from payment providers;

the episodic nature of freelance work generally or changes to demand for freelance work or interest in freelancing due to political or regulatory changes or uncertainty;

costs related to the acquisition of businesses, personnel, technologies, or intellectual property, including potentially significant amortization costs and possible write-downs;

the cost and time needed to develop and upgrade our work marketplace to incorporate new technologies or develop new or improved offerings;

the impact of outages of, and other errors, defects or disruptions on, our work marketplace and associated reputational harm;

the impact of public health pandemics, especially the COVID-19 pandemic, or other global or regional events or conditions;

fluctuations in trade and client receivables due to the timing of cash receipts from clients and the number of transactions on our work marketplace;

changes in the mix of countries in which our users are located, which impacts the amount of revenue we derive from currency exchange;

the impact of reductions in our workforce or involuntary or voluntary separations, including claims against us from departing employees or others;

changes to financial accounting standards and the interpretation of those standards that may affect the way we recognize and report our financial results, including changes
in accounting rules governing recognition of revenue;

general economic and political conditions and government regulations in the countries where we currently have significant numbers of users or where we currently operate
or may expand in the future;

fluctuations in transaction losses;

fluctuations in currency exchange rates;

operating lease expenses and other real estate expenses;

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lease termination fees or rent expense that is in excess of sublease income for a particular office space;

losses and expenses from indemnification, dispute assistance, and similar contractual obligations we owe to clients; and

non-cash  accounting  charges  such  as  stock-based  compensation  expense,  including  those  related  to  executive  compensation  arrangements,  and  depreciation  and
amortization.

The impact of one or more of the foregoing and other factors may cause our operating results and performance metrics to vary significantly. As such, we believe that quarter-to-
quarter comparisons of our operating results and performance metrics may not be meaningful and should not be relied upon as an indication of future performance. For example,
future  period-over-period  revenue  growth  rates,  when  compared  against  the  quarterly  and  full  year  results  of  2021,  may  fail  to  meet  the  expectations  of  investors  or  securities
analysts given the accelerated revenue growth experienced during such periods due to the COVID-19 pandemic and the resulting increased adoption of remote work and reduced
seasonality  experienced  during  such  periods.  If  we  fail  to  meet  or  exceed  the  expectations  of  investors  or  securities  analysts,  the  trading  price  of  our  common  stock  could  fall
substantially, and we could face costly lawsuits, including securities class action suits.

We track certain performance metrics with internal tools and do not independently verify such metrics. Certain of our performance metrics may not accurately reflect
certain details of our business, are subject to inherent challenges in measurement, and real or perceived inaccuracies in such metrics may harm our reputation and
negatively affect our business.

We track certain performance metrics, including active clients and GSV per active client, both of which we have just recently begun reporting, as well as GSV and marketplace take
rate with internal tools, which are not independently verified by any third-party. Our internal tools have a number of limitations and our methodologies for tracking these metrics may
change  over  time,  which  could  result  in  unexpected  changes  to  our  metrics,  including  the  metrics  we  report.  If  the  internal  tools  we  use  to  track  these  metrics  undercount  or
overcount performance or contain algorithmic or other technical errors, the data we report may not be accurate. In addition, limitations or errors with respect to how we measure
data (or the data that we measure) may affect our understanding of certain details of our business, which could affect our longer-term strategies. If our performance metrics are not
accurate representations of our business, user base, or traffic levels; if we discover material inaccuracies in our metrics; or if the metrics we rely on to track our performance do not
provide an accurate measurement of our business, our reputation may be harmed, we may be subject to legal or regulatory actions, and our operating and financial results could be
adversely affected. In addition, from time to time we may change the performance metrics that we track, including metrics that we report, and any new performance metrics will also
be subject to the foregoing limitations and risks. For example, in order to provide more relevant insight into our current business performance and align with how management views
the business, beginning in the third quarter of 2021, we ceased reporting the performance metrics tracking the number of core clients and client spend retention, and instead began
reporting last quarter the performance metrics tracking the number of active clients and GSV per active client.

If  we  fail  to  maintain  an  effective  system  of  disclosure  controls  and  internal  control  over  financial  reporting,  our  ability  to  produce  timely  and  accurate  financial
statements or comply with applicable laws and regulations could be impaired.

A  material  weakness  is  a  deficiency  or  combination  of  deficiencies  in  our  internal  control  over  financial  reporting  such  that  there  is  a  reasonable  possibility  that  a  material
misstatement of our consolidated financial statements would not be prevented or detected on a timely basis. As previously disclosed, we identified a number of adjustments relating
to  previously  issued  consolidated  financial  statements  that  resulted  in  a  revision  to  our  consolidated  financial  statements  as  of  and  for  the  year  ended  December  31,  2016  and
determined that this control deficiency constituted a material weakness in our internal control over financial reporting. We successfully remediated the material weakness during the
year ended December 31, 2020.

If we experience additional material weaknesses or otherwise fail to maintain an effective system of internal controls in the future, we may not be able to accurately or timely report
our financial condition or results of operations or prevent fraud, which may adversely affect investor confidence in us and, as a result, the value of our common stock. We cannot
assure you that all of our existing material weaknesses have been identified, or that we will not in the future identify additional material weaknesses. Any failure to maintain effective
disclosure controls and internal control over financial reporting could have an adverse effect on our business and results of operations and could adversely impact our business,
operating results, and financial condition.

If we are unable to assert that our internal control over financial reporting is effective, or if our independent registered public accounting firm is unable to express an opinion on the
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could lose investor confidence in the accuracy and completeness of our financial reports, which would cause the price of our common stock to decline, and we may be subject to
investigation or sanctions by the SEC. Furthermore, investor perceptions of our company may suffer if, in the future, material weaknesses are found, and this could cause the price
of our common stock to decline. In addition, if we are unable to continue to meet these requirements, we may not be able to remain listed on The Nasdaq Global Select Market.

The applicability of sales, use, and other tax laws or regulations on our business is uncertain. Adverse tax laws or regulations could be enacted or existing laws could
be  interpreted  as  applying  or  otherwise  applied  to  us  or  users  of  our  work  marketplace,  which  could  subject  us  or  our  users  to  additional  tax  liability  and  related
interest and penalties, and adversely impact our business.

The application of federal, state, local, and international tax laws to services provided over the internet is evolving. In addition to income taxes, in the United States and various
foreign jurisdictions, we may also be subject to non-income based taxes, such as payroll, sales, use, value-added, and goods and services taxes (including the “digital service tax”),
and we may also be subject to increased obligations as a withholding agent. Many of the fundamental statutes and regulations that impose these taxes were established before the
adoption and growth of the internet and ecommerce. In addition, governments are increasingly looking for ways to increase revenue, which has resulted in aggressive enforcement
and new interpretations of existing tax laws, enacting new laws and promulgating new regulations (particularly those establishing an economic nexus as a basis to collect taxes from
companies with no local presence), discussions about tax reform, and other legislative action to increase tax revenue, including through indirect taxes. New income, payroll, sales,
use,  value-added,  goods  and  services,  platform,  intermediary,  digital  services,  or  other  tax  laws,  statutes,  rules,  regulations,  or  ordinances  are  regularly  enacted  and  could  be
enacted at any time (possibly with retroactive effect), could be applied solely or disproportionately to services provided over the internet, could target certain offerings and services
offered on our work marketplace, or could otherwise affect our or our users’ tax obligations or financial position and operating results. For example, a number of U.S. states and
other jurisdictions have, within the past few years, enacted taxes on marketplace facilitators requiring online marketplaces to collect and remit taxes for first- and third-party sales on
their websites. A successful assertion that we should be collecting taxes or remitting taxes directly to states or other jurisdictions beyond those that we already collect or remit could
result in substantial tax liabilities for past transactions and additional administrative expenses, and could cause us to accrue additional estimates of taxes due, including interest and
penalties. Moreover, many countries in the EU, as well as the United Kingdom, India, and a number of other countries and organizations, such as the Organisation for Economic Co-
operation and Development, have recently proposed or recommended changes to existing tax laws or have enacted new laws that could impact our tax obligations. The impact and
burden of these regulations and proposed regulations on our business and the businesses of our users is uncertain, but may have a negative impact on our business.

We currently collect and remit indirect taxes on our fees in a number of jurisdictions and may begin collecting and remitting indirect taxes in additional jurisdictions. Our collection of
indirect taxes on our fees in these jurisdictions may increase costs to our users or cause our users to use other platforms or other alternatives that do not collect indirect taxes on
their fees, which may in turn affect our financial results. In addition, tax authorities may raise questions about, challenge or disagree with our determination as to whether we are
obligated to collect indirect taxes or our calculation, reporting, or collection of taxes and may require us to remit additional taxes and interest, and could impose associated penalties
and fees. Should any new taxes become applicable or the application of existing taxes be deemed to apply to us or our users, or if the taxes we pay are found to be deficient, our
business could be adversely impacted. We have in the past been, and may in the future be, audited by tax authorities with respect to non-income taxes, and we may have exposure
to  additional  non-income  tax  liabilities,  which  could  have  an  adverse  effect  on  our  operating  results  and  financial  condition.  In  addition,  our  future  effective  tax  rates  could  be
favorably  or  unfavorably  affected  by  changes  in  tax  rates,  changes  in  the  valuation  of  our  deferred  tax  assets  or  liabilities,  the  effectiveness  of  our  tax  planning  strategies,  or
changes in tax laws or their interpretation. Such changes could have an adverse impact on our operating results and financial condition.

Moreover, state, local, and foreign tax jurisdictions have differing rules and regulations governing reporting, sales, income, use, value-added, payroll, services, and other taxes, and
these  rules  and  regulations  can  be  complex  and  are  subject  to  varying  interpretations  and  enforcement  positions  that  may  change  over  time.  Existing  tax  laws,  statutes,  rules,
regulations, or ordinances could be interpreted, changed, modified, or applied adversely to us or our users (possibly with retroactive effect), which could require us or our users to
pay additional tax amounts on prior sales and going forward, as well as require us or our users to pay fines, penalties, and interest for past amounts. Although our terms of service
require our users to pay all applicable sales and other taxes and to indemnify us for any requirement that we pay any withholding amount to the appropriate authorities, our work
marketplace does not include functionality to easily enable users to charge any applicable taxes to one another, users may be unwilling or

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unable to pay back taxes and associated interest or penalties and may fail to indemnify us, we may determine that it would not be commercially feasible or cost-effective to seek
reimbursement, the indemnification obligation may be deemed unenforceable, or the functionality and indemnification provisions may cause users to seek out other platforms. If we
are  required  to  collect  and  pay  back  taxes  and  associated  interest  and  penalties,  or  we  are  unsuccessful  in  collecting  such  amounts  from  our  users,  we  could  incur  potentially
substantial unplanned expenses, thereby adversely impacting our operating results and cash flows. In addition, tax laws and regulations may subject us to audit by tax regulators
and require us to provide certain data and information, including user information, from our work marketplace to tax regulators in certain jurisdictions. If we are obligated to provide
such information to tax regulators in any jurisdiction, users may choose to use other platforms or other alternatives, which may in turn adversely affect our operating results and
financial condition.

Also, federal and state tax rules require collection of certain data and reporting transactions or payments above certain thresholds. Under certain circumstances, a failure to comply
with such reporting obligations may cause us to become liable to withhold a percentage of the amounts paid to talent and remit such amounts to the taxing authorities. Due to the
large number of users and transaction volume on our platform, process failures with respect to these data collection or reporting obligations could result in financial liability and other
consequences to us if we were unable to remedy such failures in a timely manner.

Additionally, our corporate structure and intercompany arrangements are subject to the tax laws of various jurisdictions, and we could be obligated to pay additional taxes, which
could adversely impact our operating results. The taxing authorities of the jurisdictions in which we operate may challenge our methodologies for pricing intercompany transactions
pursuant to the intercompany arrangements or disagree with our determinations as to the income and expenses attributable to specific jurisdictions or specific affiliates. If such a
challenge or disagreement were to occur, and our position was not sustained, we could be required to pay additional taxes, interest, and penalties.

We accrue liabilities related to tax obligations on our consolidated financial statements based on our best estimate of these liabilities, however, the ultimate amount of tax obligations
we owe may differ from the amounts recorded in our financial statements and any such difference may adversely impact our operating results in future periods in which we change
our estimates of our tax obligations or in which the ultimate tax outcome is determined.

If currency exchange rates fluctuate substantially in the future, the results of our operations, which are reported in U.S. dollars, could be adversely affected.

As  we  expand  our  international  footprint  and  make  more  services  available  to  our  users  internationally,  we  will  become  more  exposed  to  the  effects  of  fluctuations  in  currency
exchange rates. Although we expect an increasing number of sales contracts to be denominated in currencies other than the U.S. dollar in the future, all of our sales contracts are
and have historically been denominated in U.S. dollars. However, we offer clients the option to settle invoices denominated in U.S. dollars in the local currencies of several non-U.S.
countries,  and  therefore,  a  portion  of  our  revenue  is  subject  to  foreign  currency  risk.  While  we  currently  use  derivative  instruments  to  hedge  certain  exposures  to  fluctuations  in
foreign currency exchange rates, the use of such hedging activities may not offset any, or more than a portion, of the adverse financial effects of unfavorable movements in foreign
exchange rates over the limited time the hedges are in place. Moreover, a strengthening of the U.S. dollar could increase the real cost of transacting on our work marketplace to
clients located outside of the United States and could result in a loss of such clients, which could adversely affect our business, operating results, financial condition, and cash flows.

Our ability to use our net operating loss carryforwards and certain other tax attributes is limited.

As  of  December  31,  2021,  we  had  net  operating  loss  carryforwards  for  U.S.  federal  income  tax  purposes  and  California  state  income  tax  purposes  of  $444.6  million  and  $90.4
million, respectively, available to offset future taxable income. Our federal net operating loss carryforward amounts began to expire in 2019, including $14.5 million that expired in
2019,  $15.1  million  that  expired  in  2020,  and  $21.6  million  that  expired  in  2021,  and  will  continue  to  expire  in  2022  and  future  years.  The  California  state  net  operating  loss
carryforward amounts will begin to expire in 2028. Realization of these net operating loss carryforwards depends on future income, and there is a risk that our existing carryforwards
could expire unused and be unavailable to offset future income tax liabilities, which could materially and adversely affect our operating results.

In addition, under Sections 382 and 383 of the Internal Revenue Code of 1986, as amended, if a corporation undergoes an “ownership change,” generally defined as a greater than
50% change (by value) in its equity ownership over a three-year period, the corporation’s ability to use its pre-change net operating loss carryforwards and other pre-change tax
attributes, such as research tax credits, to offset its post-change income may be limited. In addition, we may experience ownership changes in the future as a result of subsequent
shifts in our stock

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ownership.  As  a  result,  if  we  earn  net  taxable  income,  our  ability  to  use  our  pre-change  net  operating  loss  carry-forwards  and  other  tax  attributes  to  offset  U.S.  federal  taxable
income may be subject to limitations, which could potentially result in increased future tax liability to us.

We may require additional capital to fund our business and support our growth, including in connection with any future acquisitions or strategic investments, and any
inability to generate or obtain such capital may adversely affect our operating results and financial condition.

In order to support our growth and respond to business challenges, such as developing new features or enhancements to our work marketplace, acquiring new technologies, and
improving our infrastructure, we have made significant financial investments in our business and we intend to continue to make such investments. In addition, we may, from time to
time, seek to acquire or strategically invest in other complementary products, technologies, or businesses. As a result, we may need to engage in equity or debt financings to obtain
the  funds  required  for  these  investments,  acquisitions,  and  other  business  endeavors.  If  we  raise  additional  funds  through  equity  or  convertible  debt  issuances,  our  existing
stockholders may suffer significant dilution and these securities could have rights, preferences, and privileges that are superior to those of holders of our common stock. If we obtain
additional funds through debt financing, we may not be able to obtain such financing on terms favorable to us. Such terms may involve additional restrictive covenants making it
difficult  to  engage  in  capital  raising  activities  and  pursue  business  opportunities,  including  potential  acquisitions  and  strategic  investments.  If  we  are  unable  to  obtain  adequate
financing  or  financing  on  terms  satisfactory  to  us  when  we  require  it,  our  ability  to  continue  to  support  our  business  growth  and  to  respond  to  business  challenges  could  be
significantly impaired and our business may be adversely affected, requiring us to delay, reduce, or eliminate some or all of our operations.

Risks Related to Ownership of Our Common Stock

The stock price of our common stock has been and may continue to be volatile, and you could lose all or part of your investment.

The market price of our common stock has been and may continue to be volatile, particularly as a result of broader stock market fluctuations and in light of the macroeconomic
uncertainty created by the COVID-19 pandemic, including as new variants of COVID-19 emerge. The market price of our common stock may fluctuate significantly in response to
numerous factors, many of which are beyond our control and some of which will be impacted by the COVID-19 pandemic and the resulting restrictions intended to prevent its spread
and macroeconomic uncertainty, including:

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actual or anticipated fluctuations in our revenue and other operating results;

changes in the financial projections we may provide to the public or our failure to meet these projections;

overall performance of the equity markets;

the economy as a whole and market conditions in our industry;

speculative trading practices by stockholders and other market participants;

rumors and market speculation involving us or other companies in our industry and/or other industries;

failure of securities analysts to initiate or maintain coverage of us, inaccurate or unfavorable research by analysts, changes in financial estimates by any securities analysts
who follow our company, or our failure to meet these estimates or the expectations of investors;

lawsuits threatened or filed against or by us or against our key personnel, litigation involving our industry, or lawsuits threatened or filed against our users relating to their
use of our work marketplace;

recruitment or departure of key personnel;

increased interest and trading in our stock from retail investors;

developments or disputes concerning our or other parties’ products, services, or intellectual property rights;

negative publicity related to the real or perceived quality or security of our work marketplace, as well as the failure to timely launch new offerings and services that gain
market acceptance;

acquisitions, strategic partnerships, joint ventures, or capital commitments;

sales of shares of our common stock by us or our stockholders, including sales of large blocks of our stock relative to the size of our public float;

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new laws or regulations or new interpretations of existing laws or regulations applicable to our business, including those governing worker classification, taxation of workers,
or withholding and remitting taxes on income or earnings;

announcements by us or our competitors of new or terminated products or services, commercial relationships, or significant technical innovations;

changes in accounting standards, policies, guidelines, interpretations, or principles;

political changes or events, such as the ongoing U.S. and global political and international relations environment; and

other events or factors, including those resulting from war, incidents of terrorism, or responses to these events.

In  addition,  the  stock  markets  have  experienced  extreme  price  and  volume  fluctuations  that  have  affected  and  continue  to  affect  the  market  prices  of  equity  securities  of  many
companies. Stock prices of many companies, and technology companies in particular, have fluctuated in a manner unrelated or disproportionate to the operating performance of
those companies and are attributable, in part, to outside factors such as the COVID-19 pandemic and its impact on the global economy. In the past, stockholders have instituted
securities class action litigation following periods of market volatility. If we were to become involved in securities litigation, it could subject us to substantial costs, divert resources
and the attention of management from our business, and adversely affect our business.

Sales of substantial amounts of our common stock in the public markets, particularly sales by our directors, executive officers, and significant stockholders, or the
perception  that  these  sales  could  occur,  could  cause  the  market  price  of  our  common  stock  to  decline  and  may  make  it  more  difficult  for  you  to  sell  your  common
stock at a time and price that you deem appropriate.

The  market  price  of  our  common  stock  could  decline  as  a  result  of  sales  of  a  large  number  of  shares  of  our  common  stock  in  the  market,  particularly  sales  by  our  directors,
executive officers, and significant stockholders. The perception that these sales might occur may also cause the market price of our common stock to decline. All shares of our
common stock are freely tradable, generally without restrictions or further registration under the Securities Act of 1933, as amended, which we refer to as the Securities Act, subject
to certain exceptions for shares held by our “affiliates” as defined in Rule 144 under the Securities Act. In addition, the shares issued upon exercise of outstanding stock options or
settlement or outstanding restricted stock units, which we refer to as RSUs, will be available for immediate resale in the United States on the open market.

Moreover, certain holders of our common stock have rights, subject to certain conditions, to require us to file registration statements for the public resale of such shares or to include
such shares in registration statements that we may file for us or other stockholders.

We  may  also  issue  our  shares  of  common  stock  or  securities  convertible  into  shares  of  our  common  stock  from  time  to  time  in  connection  with  a  financing,  an  acquisition,
investments, or otherwise. We also expect to grant additional equity awards to employees, directors, and consultants under our 2018 Equity Incentive Plan and rights to purchase
our common stock under our 2018 Employee Stock Purchase Plan. Any such issuances could result in substantial dilution to our existing stockholders and cause the market price of
our common stock to decline.

We do not intend to pay dividends for the foreseeable future.

We  have  never  declared  or  paid  any  cash  dividends  on  our  common  stock  and  do  not  intend  to  pay  any  cash  dividends  in  the  foreseeable  future.  We  anticipate  that  for  the
foreseeable future we will retain all of our future earnings for use in the development of our business and for general corporate purposes. Any determination to pay dividends in the
future will be at the discretion of our board of directors. Accordingly, investors must rely on sales of their common stock after price appreciation, which may never occur, as the only
way to realize any future gains on their investments.

Provisions in our charter documents and under Delaware law could make an acquisition of our company more difficult, limit attempts by our stockholders to replace or
remove our current management, limit our

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stockholders’ ability to obtain a favorable judicial forum for disputes with us or our directors, officers, or employees, and limit the market price of our common stock.

Provisions  in  our  restated  certificate  of  incorporation  and  amended  and  restated  bylaws  may  have  the  effect  of  delaying  or  preventing  a  change  of  control  or  changes  in  our
management. Our restated certificate of incorporation and amended and restated bylaws include provisions that:

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provide that our board of directors is classified into three classes of directors with staggered three-year terms;

permit the board of directors to establish the number of directors and fill any vacancies and newly created directorships;

require super-majority voting to amend some provisions in our restated certificate of incorporation and amended and restated bylaws;

authorize the issuance of “blank check” preferred stock that our board of directors could use to implement a stockholder rights plan;

provide that only the chairperson of our board of directors, our chief executive officer, president, lead independent director, or a majority of our board of directors will be
authorized to call a special meeting of stockholders;

prohibit stockholder action by written consent, which requires all stockholder actions to be taken at a meeting of our stockholders;

provide that the board of directors is expressly authorized to make, alter, or repeal our amended and restated bylaws; and

establish  advance  notice  requirements  for  nominations  for  election  to  our  board  of  directors  or  for  proposing  matters  that  can  be  acted  upon  by  stockholders  at  annual
stockholder meetings.

In  addition,  our  restated  certificate  of  incorporation  provides  that  the  Court  of  Chancery  of  the  State  of  Delaware  is  the  exclusive  forum  for  any  derivative  action  or  proceeding
brought on our behalf, any action asserting a breach of fiduciary duty, any action asserting a claim against us arising pursuant to the Delaware General Corporation Law, which we
refer to as the DGCL, our restated certificate of incorporation, or our amended and restated bylaws, or any action asserting a claim against us that is governed by the internal affairs
doctrine. Our amended and restated bylaws also provide that the federal district courts of the United States would be the exclusive forum for resolving any complaint asserting a
cause of action arising under the Securities Act. Any person or entity purchasing or otherwise acquiring any interest in any of our securities shall be deemed to have notice of and
consented to this provision.

These choice of forum provisions may limit a stockholder’s ability to bring a claim in a judicial forum that it finds favorable for disputes with us or any of our directors, officers, or
other employees, which may discourage lawsuits against us and our directors, officers, and other employees.

Moreover,  Section  203  of  the  DGCL  may  discourage,  delay,  or  prevent  a  change  of  control  of  our  company.  Section  203  imposes  certain  restrictions  on  mergers,  business
combinations, and other transactions between us and holders of 15% or more of our common stock.

Risks Related to Our Convertible Senior Notes

Our indebtedness could limit the cash flow available for our operations and expose us to risks that could adversely affect our business, financial condition, and results
of operations.

In August 2021, we issued convertible senior promissory notes, which we refer to as the Notes, which have an aggregate principal amount of $575.0 million. The Notes are senior,
unsecured  obligations  of  the  Company  and  will  bear  interest  at  a  rate  of  0.25%  per  year.  The  Notes  will  mature  on  August  15,  2026,  unless  earlier  redeemed,  repurchased,  or
converted in accordance with the terms of the Notes. As of December 31, 2021, we had $575.0 million indebtedness. We may also incur additional indebtedness to meet future
financing needs. Our indebtedness could have significant negative consequences for our stockholders and our business, results of operations and financial condition by, among
other things:

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increasing our vulnerability to adverse economic and industry conditions;

limiting our ability to obtain additional financing;

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requiring  the  dedication  of  a  substantial  portion  of  our  cash  flow  from  operations  to  service  our  indebtedness,  which  will  reduce  the  amount  of  cash  available  for  other
purposes;

limiting our flexibility to plan for, or react to, changes in our business;

diluting the interests of our existing stockholders as a result of issuing shares of our common stock upon conversion of the Notes; and

placing us at a possible competitive disadvantage with competitors that are less leveraged than us or have better access to capital.

Our business may not generate sufficient funds, and we may otherwise be unable to maintain sufficient cash reserves, to pay amounts due under our indebtedness and our cash
needs may increase in the future.

The capped call transactions may affect the value of our common stock.

In  connection  with  the  Notes,  we  entered  into  capped  call  transactions,  which  we  refer  to  as  Capped  Calls,  with  various  financial  institutions,  which  we  refer  to  as  the  option
counterparties. The Capped Calls are expected generally to reduce the potential dilution to our common stock upon any conversion of the Notes and/or offset any potential cash
payments we are required to make in excess of the principal amount upon conversion of any Notes, with such reduction and/or offset subject to a cap.

In addition, the option counterparties and/or their respective affiliates may modify their hedge positions by entering into or unwinding various derivatives with respect to our common
stock and/or purchasing or selling our common stock in secondary market transactions (and are likely to do so following any conversion of Notes, any repurchase of the Notes by us
on any fundamental change repurchase date, any redemption date, or any other date on which the Notes are retired by us). This activity could also cause or avoid an increase or a
decrease in the market price of our common stock.

The potential effect, if any, of these transactions and activities on the market price of our common stock will depend in part on market conditions and cannot be ascertained at this
time. Any of these activities could adversely affect the value of our common stock.

General Risks

Adverse or changing economic conditions may negatively impact our business.

Our business depends on the overall demand for labor and on the economic health of current and prospective clients that use our work marketplace. Any significant weakening of
the  economy  in  the  United  States  or  Europe  or  of  the  global  economy,  including  the  worsening  of  the  ongoing  labor  shortage  or  the  continued  rise  in  inflation,  more  limited
availability  of  credit,  a  reduction  in  business  confidence  and  activity,  decreased  government  spending,  economic  and  political  uncertainty,  financial  turmoil  affecting  the  banking
system or financial markets, trade wars and higher tariffs, a more limited market for independent professional service providers or information technology services, shifts away from
remote  work,  and  other  adverse  economic  or  market  conditions  may  adversely  impact  our  business  and  operating  results.  Global  economic  and  political  events  or  uncertainty,
including the current geopolitical uncertainty in, and potential military conflict between, Russia and Ukraine, may cause some of our current or potential users to curtail their use of
our work marketplace, and may ultimately result in new regulatory and cost challenges to our operations, including sanctions imposed in response to such events. In addition, in
January 2020, the United Kingdom formally withdrew from the EU, which we refer to as Brexit. The economic relations between the United Kingdom and the EU are now on more
restricted terms than before and there remains uncertainty around the post-Brexit regulatory environment. This uncertainty could cause significant economic disruption and further
depress consumer confidence and the economy of the United Kingdom. Our results of operations derived from revenue earned from clients and talent in the United Kingdom may
be adversely affected by such uncertainty. Brexit could also contribute to instability in global financial and foreign exchange markets, including volatility in the value of the Euro and
the British Pound, which are currencies in which we transact business. In addition, small- and medium-sized businesses were disproportionately impacted by the macroeconomic
downturn caused by the COVID-19 pandemic, some of which businesses reduced their spend on our work marketplace. These adverse conditions resulted, and may again result, in
reductions in revenue, increased operating expenses, longer sales cycles, and increased competition. There is also risk that when overall global economic conditions are positive,
our business could be negatively impacted by a decreased demand for talent as businesses utilize more full-time employees relative to their use of independent contractors. We
cannot predict the timing, strength, or duration of any economic slowdown, or any subsequent recovery generally. If the conditions in the general economy deteriorate, as a result of
the COVID-19 pandemic or otherwise, our business, financial condition, and operating results could be adversely affected.

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We  may  be  adversely  affected  by  natural  disasters  and  other  catastrophic  events,  including  the  ongoing  COVID-19  pandemic,  by  man-made  problems  such  as
terrorism, or failures of technology, that could disrupt our business operations and our business continuity and disaster recovery plans may not adequately protect us
from a serious disaster.

A  significant  natural  disaster,  such  as  an  earthquake,  blizzard,  hurricane,  fire,  flood,  or  other  catastrophic  event,  such  as  a  power  loss  or  telecommunications  failure,  or  other
technological failure resulting in the permanent destruction of data, could have a material adverse impact on our business, financial condition, and operating results. In the event of
natural disaster or other catastrophic event, we may be unable to continue our operations and may endure system interruptions, reputational harm, delays in development of our
work  marketplace,  lengthy  interruptions  in  service,  security  breaches,  and  loss  of  critical  data,  all  of  which  could  have  an  adverse  effect  on  our  operating  results.  Certain  of  our
departments are situated primarily in one geographical area and any natural disaster or catastrophic event to such area or the surrounding communities where our employees live
may impact productivity or revenue generating activities by employees based in that office. Our corporate headquarters and many key personnel are located in the San Francisco
Bay Area, a region known for seismic activity and catastrophic fires. In addition, natural disasters and other catastrophic events could affect our partners’ ability to perform services
for users on a timely basis. In the event any such partners’ information technology systems or service abilities are hindered by any of the events discussed above, our ability to
provide our work marketplace and other services may be impaired, resulting in missing financial targets for a particular quarter or year, or longer period. Further, if a natural disaster
or other catastrophic event occurs in a region from which we derive a significant portion of our revenue, users in that region may delay or forego use of our work marketplace or
other  services,  which  may  adversely  impact  our  operating  results.  In  addition,  acts  of  terrorism,  civil  disorder,  public  health  pandemics  (including  the  COVID-19  pandemic),  or
military  conflict  (including  the  potential  conflict  between  Russia  and  Ukraine)  could  cause  disruptions  in  our  business  or  the  business  and  activity  of  our  partners,  users,  or  the
economy  as  a  whole.  These  disruptions  may  be  more  severe  than  in  the  case  of  natural  disasters.  All  of  the  aforementioned  risks  may  be  exacerbated  if  our  or  our  partners’
business continuity and disaster recovery plans prove to be inadequate. To the extent that any of the above results in delays or reductions in platform availability, activities or other
services, our business, financial condition, and operating results would be adversely affected.

Item 1B. Unresolved Staff Comments.

Not applicable.

Item 2. Properties.

Our corporate headquarters are located in San Francisco, California, where we occupy facilities totaling approximately 18,500 square feet under a lease agreement that expires in
August 2024.

We also lease office space in Chicago, Illinois and rent working space in Oslo, Norway.

Given our shift to a flexible work model for our workforce, in 2021, we subleased the entirety of our former headquarters in Santa Clara, California and subleased a portion of our
current headquarters in San Francisco, California. We may determine to either close or sublease certain of our other offices. On the other hand, we may procure additional space as
we expand geographically or as we add employees. See “Note 5—Balance Sheet Components” of the notes to our consolidated financial statements included elsewhere in this
Annual Report for additional information on our leased properties.

We believe that our facilities are adequate to meet our needs for the immediate future, and that, should it be needed, suitable additional space will be available to accommodate any
such expansion of our operations.

Item 3. Legal Proceedings.

We are not a party to any material pending legal proceedings. From time to time, we may be subject to legal proceedings and claims arising in the ordinary course of business.

Item 4. Mine Safety Disclosures.

Not applicable.

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PART II

Item 5. Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities.

Market Information for Common Stock

Our common stock has been traded on The Nasdaq Global Select Market under the symbol “UPWK” since October 3, 2018. Prior to that time, there was no public market for our
common stock.

Holders of Record

As  of  January  31,  2022,  there  were  approximately  780  holders  of  record  of  our  common  stock.  Because  many  of  our  shares  of  common  stock  are  held  by  brokers  and  other
institutions on behalf of stockholders, we are unable to estimate the total number of beneficial owners of our common stock represented by these record holders.

Dividend Policy

We have never declared or paid cash dividends on our capital stock. We currently intend to retain all available funds and any future earnings for use in the operation of our business
and do not anticipate paying any dividends on our capital stock in the foreseeable future. Any future determination to declare dividends will be made at the discretion of our board of
directors, subject to applicable laws, and will depend on our financial condition, operating results, capital requirements, general business conditions, and other factors that our board
of directors may deem relevant.

Securities Authorized for Issuance Under Equity Compensation Plans

The information required by this item will be included in our Proxy Statement for the 2022 Annual Meeting of Stockholders to be filed with the SEC within 120 days of the fiscal year
ended December 31, 2021, and is incorporated herein by reference.

Stock Performance Graph

This performance graph shall not be deemed “soliciting material” or to be “filed” with the SEC for purposes of Section 18 of the Exchange Act, or otherwise subject to the liabilities
under that Section, and shall not be deemed to be incorporated by reference into any filing of Upwork Inc. under the Securities Act or the Exchange Act.

The  following  graph  shows  a  comparison  from  October  3,  2018  (the  date  our  common  stock  commenced  trading  on  The  Nasdaq  Global  Select  Market),  through  December  31,
2021, of the cumulative total returns for our common stock, the NASDAQ Composite Index and the NASDAQ 100 Technology Index, respectively. The graph assumes $100 was
invested at the market close on October 3, 2018 in the common stock of Upwork Inc. Such returns are

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based on historical results and are not intended to suggest future performance. The NASDAQ Composite Index and the NASDAQ 100 Technology Index assume reinvestment of
any dividends.

Recent Sales of Unregistered Securities

In November 2021, we issued 49,989 shares of our common stock upon the cashless exercise of a warrant to purchase up to an aggregate of 500,000 shares of common stock.
The warrant was exercised as to all 50,000 then-vested and exercisable shares. In lieu of a cash payment, the holder of the warrant surrendered 11 shares of common stock to
cover  the  exercise  price  in  accordance  with  the  terms  of  the  warrant.  The  offer,  sale,  and  issuance  of  these  securities  was  deemed  to  be  exempt  from  registration  under  the
Securities  Act  in  reliance  on  Section  4(a)(2)  of  the  Securities  Act.  The  recipient  of  securities  acquired  the  securities  for  investment  only  and  not  with  a  view  to  or  for  sale  in
connection  with  any  distribution  thereof  and  appropriate  legends  were  affixed  to  the  securities  issued  in  this  transaction.  The  recipient  of  the  securities  was  an  accredited  or
sophisticated person and had adequate access, through business or other relationships, to information about us. See “Note 8—Preferred and Common Stock” of the notes to our
consolidated financial statements included elsewhere in this Annual Report for additional information on the common stock warrant.

Use of Proceeds

None.

Issuer Purchases of Equity Securities

None.

Item 6. [Reserved]

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Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations.

You should read the following discussion and analysis of our financial condition and results of operations together with the sections titled “Business” and “Risk Factors” and the
consolidated financial statements and related notes included elsewhere in this Annual Report. This discussion contains forward-looking statements based upon current expectations
that  involve  risks  and  uncertainties,  as  well  as  assumptions  that  may  never  materialize  or  that  may  be  proven  incorrect.  Our  actual  results  may  differ  materially  from  those
anticipated in these forward-looking statements as a result of various factors, including those discussed in the sections titled “Special Note Regarding Forward-Looking Statements”
and “Risk Factors” and in other parts of this Annual Report.

Overview

Business

Independent  talent  is  an  increasingly  sought-after,  critical,  and  expanding  segment  of  the  global  workforce.  We  operate  the  world’s  largest  work  marketplace  that  connects
businesses with independent talent, as measured by GSV. GSV represents the total amount that clients spend on both our marketplace offerings and our managed services offering
as  well  as  additional  fees  we  charge  to  talent  for  other  services.  Talent  includes  independent  professionals  and  agencies  of  varying  sizes.  The  clients  on  our  work  marketplace
range in size from small businesses to Fortune 100 companies. With users in over 180 countries, our work marketplace enabled $3.5 billion of GSV for the year ended December
31, 2021. For purposes of determining countries where we enable GSV, we include both the countries in which the clients that paid for the applicable services are located, as well as
the countries in which talent that provided those services are located.

As a global work marketplace that connects talent and clients regardless of their location, our GSV originates from around the world. Of the $3.5 billion of GSV enabled on our work
marketplace in 2021, approximately 25% was generated from U.S. talent, which is our largest talent geography in each of 2021, 2020, and 2019, as measured by GSV, while talent
in India and the Philippines remained our next largest talent geographies in all three years. Of the $2.5 billion and $2.1 billion of GSV enabled on our work marketplace in 2020 and
2019, respectively, approximately 25% and 27%, respectively, was generated from talent in the United States.

Approximately 66% of our GSV in 2021 was generated from U.S. clients, compared to approximately 67% and 68% of GSV in 2020 and 2019, respectively, with clients in no other
country representing more than 10% of our GSV in any year.

We generate revenue from both talent and clients, with a majority of our revenue generated from service fees charged to talent. We also generate revenue from fees charged to
both clients and talent for other services, such as for transacting payments through our work marketplace, premium offerings, purchases of Connects, foreign currency exchange
when clients choose to pay in currencies other than the U.S. dollar, and our Upwork Payroll offering. In addition, we provide a managed services offering where we engage talent to
complete projects, directly invoice the client, and assume responsibility for work performed.

Financial Highlights for 2021

In  2021,  we  continued  to  evolve  our  offerings,  brand  positioning,  and  marketing  to  better  address  large  enterprise  and  other  clients  and  prospects  with  larger,  longer-term
independent talent needs. We prioritized our advertising, marketing, and offering development efforts to reach those new and existing clients seeking to engage remote talent in light
of the shift toward remote work, due in part to the COVID-19 pandemic. As a result of these efforts, our work marketplace enabled $3.5 billion of GSV in 2021, representing a year-
over-year increase of 41%, and we experienced increases in user acquisition and the number of active clients, which fueled marketplace revenue. For the year ended December 31,
2021,  marketplace  revenue  increased  by  $124.2  million,  or  37%,  compared  to  2020.  Additionally,  we  increased  our  investment  in  brand  marketing  and  to  a  lesser  extent,  our
investment in sales by expanding our sales team. We generated a net loss of $56.2 million in 2021 compared to a net loss of $22.9 million in 2020. Our adjusted EBITDA was $19.1
million in 2021, an increase of 36% from 2020. Adjusted EBITDA is a financial measure that is not prepared in accordance with, and is not an alternative to, financial measures
prepared in accordance with U.S. GAAP. See “—Non-GAAP Financial Measures” below for the definition of adjusted EBITDA and information regarding our use of adjusted EBITDA
and a reconciliation of net loss to adjusted EBITDA.

The ongoing COVID-19 pandemic and the resulting restrictions intended to prevent its spread have continued to accelerate the secular shift toward remote and independent work,
and, with our unique, remote-based business model, the pandemic has not impacted our clients’ access to highly-skilled talent to complete short- and long-term projects on our work
marketplace. While we have not incurred significant disruptions to our business thus far from

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the ongoing COVID-19 pandemic, at this time, we are unable to fully assess the aggregate impact it will have on our business due to various uncertainties, which include, but are
not limited to, the duration of the pandemic, its effect on the economy, its impact to the businesses of our clients, actions that may be taken by governmental authorities related to
the  pandemic,  and  other  factors  identified  in  Part  I,  Item  1A  “Risk  Factors”  in  this  Annual  Report,  including  the  risk  factor  titled  “Our  business  experienced,  and  may  again
experience, an adverse impact from the ongoing COVID-19 pandemic, including as new variants of COVID-19 emerge. In addition, the positive impacts on our business resulting
from the shift to remote work during the pandemic may not continue as the pandemic subsides and the restrictions intended to prevent its spread are relaxed or lifted.”

Key Financial and Operational Metrics

We monitor the following key financial and operational metrics to evaluate our business, measure our performance, identify trends affecting our business, formulate business plans,
and make strategic decisions.

Our key metrics were as follows as of or for the periods presented:

(In thousands, except percentages)
GSV

Marketplace revenue

Marketplace take rate

Net loss

Adjusted EBITDA

(1)

Active clients

GSV per active client

2021

% Change

2020

% Change

2019

% Change

As of or for the Year Ended December 31,

$

$

$

$

$

3,546,774 

462,340 

13.2 %

(56,240)

19,127 

771 

4,599 

41 % $

37 % $

(0.4)%

(146)% $

36 % $

22 %
15 % $

2,523,649 

338,152 

13.6 %

(22,867)

14,022 

633 

3,989 

21 % $

26 % $

0.5 %

(37)% $

89 % $

17 %
3 % $

2,087,055 

268,284 

13.1 %

(16,659)

7,438 

540 

3,864 

19 %

20 %

0.1 %

16 %

95 %

9 %

9 %

(1)

Adjusted EBITDA is not prepared in accordance with, and is not an alternative to, financial measures prepared in accordance with U.S. GAAP. See “—Non-GAAP Financial
Measures” below for the definition of adjusted EBITDA and for information regarding our use of adjusted EBITDA and a reconciliation of adjusted EBITDA to net loss, the most
directly comparable financial measure prepared under U.S. GAAP.

As discussed below with respect to each key metric, we believe these key financial and operational metrics are useful to evaluate period-over-period comparisons of our business
and in understanding our operating results, and management uses these metrics to track our performance. For a discussion of limitations in the measurement of our key financial
and  operational  metrics,  see  “Risk  Factors—We  track  certain  performance  metrics  with  internal  tools  and  do  not  independently  verify  such  metrics.  Certain  of  our  performance
metrics may not accurately reflect certain details of our business, are subject to inherent challenges in measurement, and real or perceived inaccuracies in such metrics may harm
our reputation and negatively affect our business.”

Gross Services Volume (GSV)

GSV  includes  both  client  spend  and  additional  fees  charged  for  other  services.  Client  spend,  which  we  define  as  the  total  amount  that  clients  spend  on  both  our  marketplace
offerings  and  our  managed  services  offering,  is  the  primary  component  of  GSV.  GSV  also  includes  fees  charged  to  talent,  such  as  for  transacting  payments  through  our  work
marketplace, user memberships, and purchases of Connects, and foreign currency exchange.

GSV is an important metric because it represents the amount of business transacted through our work marketplace. Our marketplace revenue is primarily comprised of the service
fees paid by talent as a percentage of the total amount talent charges clients for services accessed through our work marketplace. Therefore, marketplace revenue is correlated to
GSV, and we believe that our marketplace revenue will grow as GSV grows, although they could grow at different rates. For a discussion of how we measure and evaluate the
correlation between marketplace revenue and GSV, see “—Marketplace Take Rate” below. Growth in the number of active clients and GSV per active client are the primary drivers
of GSV, and we expect the trends discussed in “—Active Clients and GSV per Active Client,” below, to affect the rate at which GSV grows. We derive a substantial portion of our
GSV and revenue from small- and medium-sized businesses. In 2021, we continued to evolve our offerings, brand positioning, and marketing to better address large enterprise and
other clients and prospects with larger, longer-term independent talent needs. Additionally, we have prioritized our advertising, marketing, and product development efforts to reach
those new and existing clients seeking to engage remote talent in light of the acceleration in the shift toward remote work, due in part to the pandemic. As a result, of these efforts,
our work marketplace enabled $3.5 billion of GSV in 2021, representing a year-over-year increase of 41%. We expect our GSV to fluctuate between periods due to a

54

number of factors, including the current COVID-19 pandemic and its impact on our clients’ businesses; the number of Sundays (i.e., the day we have the contractual right to bill and
recognize revenue for the majority of our talent service fees each week) or the number of Mondays (i.e., the day we have the contractual right to bill and recognize revenue for a
substantial portion of our client fees each week) in any given quarter; and the volume of projects that are posted by clients on our work marketplace, the characteristics of those
projects, such as size, duration, and pricing, and the availability and qualifications of talent to complete those projects.

Marketplace Revenue

Marketplace  revenue,  which  represents  the  majority  of  our  revenue,  consists  primarily  of  revenue  derived  from  our  Upwork  Basic,  Plus,  and  Enterprise  offerings.  We  generate
marketplace revenue from both talent and clients. Revenue from our Upwork Basic and Plus offerings are primarily comprised of talent service fees, and to a lesser extent, payment
processing and administration fees charged to clients. Revenue from our Upwork Enterprise offering, which we refer to as Enterprise Revenue, includes all client fees, subscriptions,
and talent service fees. We also generate marketplace revenue from fees for premium offerings associated with our Upwork Basic, Plus, and Enterprise offerings, including talent
memberships, purchases of Connects, and other services, such as foreign currency exchange when clients choose to pay in currencies other than the U.S. dollar, and our Upwork
Payroll offering.

Marketplace revenue is the primary driver of our business, and we believe it provides comparability to other online marketplaces. The growth rate of marketplace revenue fluctuates
in relation to the growth rate of GSV. Therefore, marketplace revenue is correlated to GSV, and we believe that our marketplace revenue will grow as GSV grows, although they
could grow at different rates. In 2021, we prioritized our advertising, marketing, and product development efforts to reach those new and existing clients seeking to engage remote
talent in light of the acceleration in the shift toward remote work, due in part to the COVID-19 pandemic. As a result, we experienced increases in user acquisition and growth in the
number of active clients, which drove an increase in talent billings, and, in turn, drove an increase in marketplace revenue. We expect our marketplace revenue growth rates to
continue to vary from period to period due to a variety of other factors such as the impact of the COVID-19 pandemic and any resulting macroeconomic impact on the businesses
and spending behavior of our current and prospective clients; the number of Sundays (i.e., the day we have the contractual right to bill and recognize revenue for the majority of our
talent service fees each week) or the number of Mondays (i.e., the day we have the contractual right to bill and recognize revenue for a substantial portion of our client fees each
week) in any given quarter; the lapping of significant launches of new products, pricing changes, and other monetization efforts; the number of active clients and their spend on our
work marketplace; and the ability of the recent and continued investment in our enterprise sales team to accelerate the acquisition of, and achieve increased spend from, Upwork
Enterprise clients, and the timing of those results.

Marketplace Take Rate

Marketplace  take  rate  measures  the  correlation  between  marketplace  revenue  and  marketplace  GSV  and  is  calculated  by  dividing  marketplace  revenue  by  marketplace  GSV.
Marketplace take rate is an important metric because it is the key indicator of how well we monetize spend on our work marketplace from our Upwork Basic, Plus, Enterprise, and
other premium offerings. More higher value relationships and higher spend per client results in a larger percentage of business activity on our work marketplace being priced at the
lower rates of our tiered service fee structure. During the year ended December 31, 2021, our marketplace take rate decreased as clients matured into higher value clients and
continue to increase their spend with particular talent, which resulted in a higher mix of talent at the lower rates of our tiered service fee structure. Additionally, in the fourth quarter of
2020,  to  drive  GSV,  we  increased  the  number  of  free  Connects  issued  to  talent,  which  drove  revenue  and  GSV  but  also  resulted  in  talent  purchasing  fewer  Connects  and
memberships during the year ended December 31, 2021, which resulted in slightly lower revenue as a percentage of GSV during the year ended December 31, 2021. On the other
hand, we intend to continue our efforts to better address large enterprise and other clients and prospects with larger, longer-term independent talent needs through our Upwork
Enterprise and other premium offerings. These offerings have take rates that are higher than the rest of our business, which partially offsets the trend of lower rates as relationships
and clients mature into higher value clients with increased spend. Additionally, we are working on a number of initiatives that could also have a positive impact on marketplace take
rate, and we will continue to introduce new or modify existing offerings or other services and features. As a result of these efforts, over the course of 2022, we expect marketplace
take rate to increase slightly. However, we also generally expect our marketplace take rate to vary from period to period as marketplace revenue and GSV vary as a result of a
variety of factors, such as the number of Sundays (i.e., the day we have the contractual right to bill and recognize revenue for the majority of our talent service fees each week) or
the number of Mondays (i.e., the day we have the contractual right to bill and recognize revenue for a substantial portion of our client fees each week) in any given quarter; pricing

55

changes; the ability of the recent and continued investment in our enterprise sales team to accelerate the acquisition of, and achieve increased spend from, our Upwork Enterprise
clients and the timing of those results; and ongoing efforts to improve processes on our work marketplace, including project proposals and purchases of Connects, among others.

Active Clients and GSV per Active Client

We  define  an  active  client  as  a  client  that  has  had  spend  activity  on  our  work  marketplace  during  the  12  months  preceding  the  date  of  measurement.  GSV  per  active  client  is
calculated  by  dividing  total  GSV  during  the  four  quarters  ended  on  the  date  of  measurement  by  the  number  of  active  clients  on  the  date  of  measurement.  We  believe  that  the
number of active clients and GSV per active client are indicators of the growth and overall health of our business. The number of active clients is a primary driver of GSV and, in
turn, marketplace revenue.

In  2021,  we  continued  to  execute  on  our  strategic  initiatives,  including  investing  in  research  and  development  to  build  new  product  features  and  prioritizing  our  advertising  and
marketing efforts to drive brand awareness and accelerate the acquisition of new and existing clients seeking to engage independent talent. As a result, the number of active clients
increased  22%  as  of  December  31,  2021  compared  to  December  31,  2020.  Additionally,  we  have  seen  continued  acceleration  in  the  growth  of  GSV  per  active  client  as  an
increasing number of clients continue to mature into higher-value clients and expand their spend on our work marketplace. As a result, our GSV per active client increased 15% as
of December 31, 2021 compared to December 31, 2020.

We continue to see businesses of all sizes use our work marketplace in a recurring way for larger, more complex projects, and we expect the number of active clients and GSV per
active client to continue to increase over time but could vary quarter by quarter depending, in part, on the extent to which the COVID-19 pandemic and any resulting macroeconomic
downturn impacts our business, the businesses of our clients, and other factors identified in the section titled “Risk Factors” included elsewhere in this Annual Report, including the
risk factor titled “Our business experienced, and may again experience, an adverse impact from the ongoing COVID-19 pandemic, including as new variants of COVID-19 emerge.
In  addition,  the  positive  impacts  on  our  business  resulting  from  the  shift  to  remote  work  during  the  pandemic  may  not  continue  as  the  pandemic  subsides  and  the  restrictions
intended to prevent its spread are relaxed or lifted.”

While continued use of our work marketplace by talent is a factor that impacts our ability to attract and retain clients, we currently have a significant surplus of talent in relation to the
number of clients actively engaging talent for most categories of services on our work marketplace. As a result of this surplus, we primarily focus our efforts on retaining client spend
and acquiring new clients, as opposed to acquiring new talent and retaining existing talent. Moreover, we generate revenue when clients engage and pay talent, and therefore, our
key metrics and operating results are directly impacted by client spend. Additionally, the number of talent retained between periods is merely one of many factors that may impact
client spend in a particular period and is not a primary driver of our key metrics and operating results.

Cohort Analysis

Client Spend by Annual Client Cohort

Our growth has been driven, in significant part, by retaining client spend from existing clients as we grow our client base. As illustrated in the chart below, we have been able to
retain client spend over long periods of time with clients in historical cohorts continuing to spend meaningfully on our work marketplace. A client belongs to an annual cohort based
on the date of first spend activity with talent. For example, the 2016 cohort includes all clients that had their first spend activity with talent between January 1, 2016 and December
31, 2016. Since 2016, each new annual cohort’s first-year spend has exceeded the first-year spend of the prior year’s annual cohort. For example, for the

56

years ended December 31, 2021, 2020, and 2019, client spend from new client cohorts was $537.9 million, $407.9 million, and $298.8 million, respectively.

Components of Our Results of Operations

Revenue

Marketplace Revenue. Marketplace revenue is generated from our Upwork Basic, Plus, Enterprise, and other premium offerings. Under these marketplace offerings, we generate
revenue  from  both  talent  and  clients.  Marketplace  revenue,  which  represents  the  majority  of  our  total  revenue,  is  primarily  comprised  of  the  service  fees  paid  by  talent  as  a
percentage of the total amount that talent charge clients for services accessed through our work marketplace and, to a lesser extent, payment processing and administration fees
paid by clients.

Our Upwork Basic and Plus offerings provide clients with access to talent with verified work history and client feedback on our work marketplace, the ability to instantly match with
the right talent, and built-in collaboration features. For talent working with clients that are on our Upwork Basic and Plus offerings, we have a tiered talent service fee schedule based
on cumulative lifetime billings by talent to each client. Talent typically pays us 20% of the first $500, 10% for the next $9,500, and then 5% for any amount over $10,000 they bill to
each  client  through  our  work  marketplace.  We  recognize  revenue  on  Sundays  of  each  week  for  the  majority  of  our  tiered  talent  service  fees  as  that  is  the  day  we  have  the
contractual right to bill talent for the service fees. To a lesser extent, we also generate revenue from talent through membership fees, purchases of Connects, and withdrawal and
other fees.

In addition, we generate marketplace revenue from our Upwork Basic and Plus offerings by charging clients a payment processing and administration fee. Clients using our Upwork
Basic offering pay a fee equal to 3% of their client spend. We recognize revenue on Mondays of each week for a substantial portion of our client fees as that is the day we have the
contractual right to bill the fees. Clients using our Upwork Plus offering pay a flat fee of approximately $50 per month for additional features and pay a fee equal to 3% of their client
spend unless they pay via ACH (in which case, provided all eligibility criteria are met, the fee is waived). To a lesser extent, we also

57

generate revenue from clients through foreign currency exchange fees when clients choose to pay in currencies other than the U.S. Dollar.

Our  Upwork  Enterprise  offering,  which  is  designed  for  larger  clients  with  at  least  250  employees,  includes  access  to  additional  product  features,  premium  access  to  top  talent,
professional services, custom reporting, and flexible payment terms. For our Upwork Enterprise offering, we charge clients a monthly or annual subscription fee and a service fee
calculated  as  a  percentage  of  the  client’s  spend  on  talent  services,  in  addition  to  the  service  fees  paid  by  talent.  Additionally,  Upwork  Enterprise  clients  can  also  subscribe  to  a
compliance  offering  that  includes  worker  classification  services  for  an  additional  fee  and  may  also  choose  to  use  our  work  marketplace  to  engage  talent  that  were  not  originally
sourced through our work marketplace for a lower fee percentage.

One of our premium offerings, Upwork Payroll, is available to clients when talent are classified as employees for engagements on our work marketplace. The client enters into an
Upwork Payroll agreement with us, and we separately contract with unrelated third-party staffing providers that provide employment services to such clients.

In 2021, we prioritized our advertising, marketing, and product development efforts to reach those new and existing clients seeking to engage remote talent. We intend to continue
to focus on these efforts to attract new users, including large enterprise and other clients and prospects with larger, longer-term independent talent needs, as well as talent that meet
the criteria sought by such clients.

Managed Services Revenue. Through our managed services offering, we are responsible for providing services and engaging talent directly or as employees of third-party staffing
providers to perform services for clients on our behalf. The talent providing services in connection with our managed services include independent talent and agencies of varying
sizes. Under U.S. GAAP, we are deemed to be the principal in these managed services arrangements and therefore recognize the entire GSV of managed services projects as
managed  services  revenue,  as  compared  to  recognizing  only  the  percentage  of  the  client  spend  that  we  receive,  as  we  do  with  our  marketplace  offerings.  Managed  services
revenue  grew  at  a  slower  rate  than  our  marketplace  revenue  in  2021  compared  to  2020,  as  we  primarily  focused  on  increasing  client  usage  of  and  spend  on  our  marketplace
offerings during the year ended December 31, 2021.

Cost of Revenue and Gross Profit

Cost of Revenue.  Cost  of  revenue  consists  primarily  of  the  cost  of  payment  processing  fees,  amounts  paid  to  talent  to  deliver  services  for  clients  under  our  managed  services
offering,  personnel-related  costs  for  our  services  and  support  personnel,  third-party  hosting  fees  for  our  use  of  AWS,  and  the  amortization  expense  associated  with
capitalized  internal-use  software  and  platform  development  costs.  We  define  personnel-related  costs  as  salaries,  bonuses,  benefits,  travel  and  entertainment,  and  stock-based
compensation costs for employees and the costs related to other service providers we engage.

We expect cost of revenue to increase in absolute dollars in future periods due to higher payment processing fees, personnel-related costs, and third-party hosting fees in order to
support growth on our work marketplace. Amounts paid to talent in connection with our managed services offering are tied to the volume of managed services used by our clients.
The level and timing of all of these items could fluctuate and affect our cost of revenue in the future.

Gross Profit and Gross Margin. Our gross profit and gross margin may fluctuate from period to period. Such fluctuations may be influenced by our revenue, the mix of payment
methods that our clients choose, the timing and amount of investments to expand hosting capacity, our continued investments in our services and support teams, the timing and
amounts paid to talent in connection with our managed services offering, and the amortization expense associated with capitalized internal-use software and platform development
costs.  In  addition,  gross  margin  will  be  impacted  by  fluctuations  in  our  revenue  mix  between  marketplace  revenue  and  managed  services  revenue.  For  example,  our  managed
services revenue grew at a slower rate than our marketplace revenue in 2021 compared to 2020, which caused gross margin to increase. We expect gross profit to increase in
absolute dollars in future periods, although gross margin, expressed as a percentage of total revenue, may vary from period to period.

Operating Expenses

Research  and  Development.  Research  and  development  expense  primarily  consists  of  personnel-related  costs.  Research  and  development  costs  are  expensed  as  incurred,
except to the extent that such costs are associated with internal-use software and platform development that qualifies for capitalization. In 2021, we made significant investments to
build  new  product  features,  launch  new  offerings,  and  increase  the  size  of  our  research  and  development  workforce,  and  we  believe  continued  investments  in  research  and
development are important to attain our strategic objectives. As a result, we expect research and development expense to increase in absolute dollars in future periods, although
this expense, expressed as a percentage of total revenue, may vary from period to period.

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Sales and Marketing.  Sales  and  marketing  expense  consists  primarily  of  expenses  related  to  advertising  and  marketing  activities,  as  well  as  personnel-related  costs,  including
sales  commissions,  which  we  expense  as  they  are  incurred.  In  2021,  we  continued  evolving  our  offerings,  products,  brand  positioning,  and  marketing  to  better  address  large
enterprise and other clients and prospects with larger, longer-term independent talent needs. We made significant investments in marketing to acquire new clients and drive brand
awareness, and we expect to increase these investments in 2022. Additionally, in the fourth quarter of 2021, we began increasing our investment in sales by expanding our sales
team,  and  we  expect  this  expansion  to  continue  through  2022  as  we  increase  our  efforts  to  acquire  clients  through  our  Upwork  Enterprise  offering.  As  a  result,  we  expect  this
expense to increase in absolute dollars in future periods, although this expense expressed as a percentage of total revenue may vary from period to period.

General and Administrative. General and administrative expense consists primarily of personnel-related costs for our executive, finance, legal, human resources, and operations
functions; outside consulting, legal, and accounting services; impairment expense; and insurance.

To  achieve  our  strategic  objectives,  we  expect  to  continue  to  invest  in  corporate  infrastructure  and  to  incur  additional  general  and  administrative  expenses,  including  increased
stock-based compensation expense related to executive compensation arrangements, legal and accounting costs, insurance premiums, and compliance costs. Additionally, in 2020
we shifted to a flexible work model for our workforce and are evaluating our current need for office space. As a result, we may determine to either close or sublease certain of our
offices,  either  of  which  could  result  in  further  impairment  charges  being  recognized  in  general  and  administrative  expense.  As  a  result,  we  expect  general  and  administrative
expense to increase in absolute dollars in future periods, although this expense, expressed as a percentage of total revenue, may vary from period to period.

Provision for Transaction Losses. Provision for transaction losses consists primarily of losses resulting from fraud and bad debt expense associated with our trade and client
receivables balance and transaction losses associated with chargebacks. Provisions for these items represent estimates of losses based on our actual historical incurred losses and
other factors. We expect provisions for transaction losses to increase proportionally as GSV grows. As a result, we expect provision for transaction losses to increase in absolute
dollars in future periods, although expressed as a percentage of total revenue, this expense may vary from period to period.

Interest Expense

Interest expense consists of interest on our outstanding borrowings.

Other (Income) Expense, Net

Other  (income)  expense,  net  consists  primarily  of  gains  and  losses  from  foreign  currency  exchange  transactions  and  interest  income  that  we  earn  from  our  deposits  in  money
market funds and investments in marketable securities.

Income Tax Benefit (Provision)

We  account  for  income  taxes  in  accordance  with  the  asset  and  liability  method.  Under  the  asset  and  liability  method,  deferred  assets  and  liabilities  are  recognized  based  upon
anticipated future tax consequences attributable to differences between financial statement carrying amounts of assets and liabilities and their respective tax bases. The provision
for income taxes is comprised of the current tax liability and the change in deferred tax assets and liabilities. We establish a valuation allowance to the extent that it is more likely
than not that deferred tax assets will not be recoverable against future taxable income.

Deferred tax assets and liabilities are measured using the enacted tax rates that will be in effect for the years in which those tax assets are expected to be realized or settled. We
regularly assess the likelihood that deferred tax assets will be realized from recoverable income taxes or recovered from future taxable income based on the realization criteria set
forth in the relevant authoritative guidance. To the extent that we believe any amounts are less likely than not to be realized, we record a valuation allowance to reduce our deferred
tax assets. The realization of deferred tax assets is dependent upon future earnings, if any, the timing and amount of which are uncertain. Accordingly, the net deferred tax assets
have  been  fully  offset  by  a  valuation  allowance.  If  we  subsequently  realize  deferred  tax  assets  that  were  previously  determined  to  be  unrealizable,  the  respective  valuation
allowance would be reversed, resulting in an adjustment to earnings in the period such determination is made.

In addition, the calculation of tax liabilities involves dealing with uncertainties in the application of complex tax regulations. We recognize potential liabilities based on an estimate of
whether,  and  the  extent  to  which,  additional  taxes  will  be  due.  We  account  for  uncertain  tax  positions  in  accordance  with  the  relevant  guidance,  which  prescribes  a  recognition
threshold and measurement approach for uncertain tax positions taken or expected to be taken in our

59

income tax return, and also provides guidance on recognition, classification, interest and penalties, accounting in interim periods, disclosure, and transition. The guidance utilizes a
two-step approach for evaluation of uncertain tax positions. The first step is to determine if the weight of available evidence indicates a tax position is more likely than not to be
sustained upon audit. The second step is to measure the tax benefit as the largest amount that is more likely than not to be realized on ultimate settlement. A liability is reported for
unrecognized tax benefits resulting from uncertain tax positions taken or expected to be taken in a tax return. Any interest and penalties related to unrecognized tax benefits are
recorded as income tax expense.

Results of Operations

The following table sets forth our consolidated results of operations for the years ended December 31, 2021, 2020, and 2019:

(In thousands)
Revenue:

Marketplace

Managed services

Total revenue

Cost of revenue

(1)

Gross profit
Operating expenses

Research and development

(1)

Sales and marketing

(1)

General and administrative

(1)

Provision for transaction losses

Total operating expenses

Loss from operations

Interest expense

Other income, net

Loss before income taxes

Income tax provision

Net loss

(1) 

Includes stock-based compensation expense as follows:

Cost of revenue

Research and development

Sales and marketing

General and administrative

Total

2021

2020

2019

$

462,340  $

338,152  $

40,457 

502,797 

135,508 

367,289 

119,083 

183,294 

113,081 

6,048 

421,506 

(54,217)

2,180 

(279)

(56,118)

(122)

35,476 

373,628 

104,267 

269,361 

83,471 

133,225 

71,518 

3,555 

291,769 

(22,408)

778 

(469)

(22,717)

(150)

$

$

$

(56,240) $

(22,867) $

794  $

779  $

16,232 

5,923 

30,643 

9,783 

4,440 

10,506 

53,592  $

25,508  $

268,284 

32,278 

300,562 

88,144 

212,418 

64,027 

95,891 

67,327 

3,905 

231,150 

(18,732)

1,306 

(3,407)

(16,631)

(28)

(16,659)

456 

6,471 

2,609 

9,262 

18,798 

A discussion regarding our financial condition and results of operations for the year ended December 31, 2020 compared to the year ended December 31, 2019 is included in Part
II, Item 7, “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Results of Operation,” included in our Annual Report on Form 10-K for the
year ended December 31, 2020, filed with the SEC on February 24, 2021.

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Comparison of the Years Ended December 31, 2021 and 2020

Revenue

(In thousands, except percentages)

Marketplace

Percentage of total revenue

Managed services

Percentage of total revenue

Total revenue

Year Ended December 31,

2021

2020

Change

$

%

$

$

$

462,340 

92 %

40,457 

8 %

502,797 

$

$

$

338,152 

91 %

35,476 

9 %

124,188 

4,981 

373,628 

$

129,169 

37 %

14 %

35 %

For the year ended December 31, 2021, total revenue was $502.8 million, representing an increase of $129.2 million, or 35%, as compared to 2020.

In 2021, we continued to execute on our strategic initiatives, including investing in research and development to build new product features, prioritizing our advertising efforts to
reach new and existing clients seeking to engage independent talent, and investing in marketing to accelerate the acquisition of new clients and drive brand awareness. As a result,
the number of active clients increased 22% as of December 31, 2021 compared to December 31, 2020, and our GSV per active client increased 15% as of December 31, 2021
compared to December 31, 2020. The growth in active clients and GSV per active client contributed to the growth of GSV and marketplace revenue. For the year ended December
31, 2021, GSV increased 41%, as compared to the same period in 2020. Marketplace revenue was driven by client spend, which for the year ended December 31, 2021, drove an
increase in talent service fees of 36%, as compared to the same period in 2020, and an increase in client payment processing and administrative fees of 42%, as compared to the
same period in 2020.

Additionally,  in  2021,  we  continued  our  efforts  to  better  address  large  enterprise  and  other  clients  and  prospects  with  larger,  longer-term  independent  talent  needs  through  our
Upwork Enterprise and other premium offerings. As a result, Enterprise Revenue increased 73% to $34.9 million, which fueled marketplace revenue for the year ended December
31, 2021. Marketplace revenue represented 92% of total revenue and increased by $124.2 million, or 37%, compared to 2020. Marketplace revenue grew more slowly than GSV
from our marketplace offerings in 2021, and for the year ended December 31, 2021, our marketplace take rate was 13.2%, as compared to 13.6% for the same period in 2020. This
trend was the result of a few factors. In particular, clients are maturing into higher value clients and continue to increase their spend with particular talent, which resulted in a higher
mix of talent at the lower rates of our tiered service fee structure. Additionally, in the fourth quarter of 2020, to drive GSV, we increased the number of free Connects issued to talent,
which drove revenue and GSV but also resulted in talent purchasing fewer Connects and memberships during the year ended December 31, 2021, which resulted in slightly lower
revenue as a percentage of GSV during the year ended December 31, 2021.

Managed  services  revenue  represented  8%  and  9%  of  total  revenue  for  the  years  ended  December  31,  2021  and  2020,  respectively.  For  the  year  ended  December  31,  2021,
managed services revenue increased by $5.0 million, or 14%, compared to 2020.

Cost of Revenue and Gross Margin

(In thousands, except percentages)
Cost of revenue
Components of cost of revenue:

Costs of talent services to deliver managed services
Other components of cost of revenue

Total gross margin

Year Ended December 31,

2021

2020

Change

$

%

$

135,508 

$

104,267 

$

31,871 
103,637 

73 %

28,703 
75,564 

72 %

31,241 

3,168 
28,073 

30 %

11 %
37 %

For the year ended December 31, 2021, cost of revenue increased by $31.2 million, or 30%, compared to 2020. For the year ended December 31, 2021, cost of revenue increased
primarily as a result of increases in payment processing fees of $23.1 million, as compared to the same period in 2020, primarily due to increased client spend, as well as increases
in  cost  of  talent  services  to  deliver  managed  services  resulting  from  increases  in  managed  services  revenue  for  the  year  ended  December  31,  2021,  as  compared  to  the  same
period in 2020. Additionally, for

61

the year ended December 31, 2021, third-party hosting costs increased $2.4 million, as compared to the same period in 2020, driven by our use of two AWS data centers during the
period in connection with our migration from the AWS facility in California to the AWS facility in Oregon.

Research and Development

(In thousands, except percentages)
Research and development

Percentage of total revenue

Year Ended December 31,

2021

2020

$

119,083 

$

24 %

83,471 

$

22 %

Change

$

35,612 

%

43 %

For  the  year  ended  December  31,  2021,  research  and  development  expense  increased  by  $35.6  million,  or  43%,  as  compared  to  2020.  The  increase  was  primarily  due  to  our
ongoing and significant investments to build new product features, launch new offerings, and enhance the user experience. Specifically, investments we made to increase the size
of  our  research  and  development  workforce  resulted  in  increases  in  personnel-related  costs  of  $26.0  million,  as  compared  to  the  same  period  in  2020,  as  well  as  increases  in
software licenses of $2.6 million, outside consultants of $1.5 million, and depreciation and other costs of $3.1 million. Additionally, due to the timing of new projects, we capitalized
less internal-use software and platform development costs than we did in 2020, when we capitalized an incremental $2.4 million.

Sales and Marketing

(In thousands, except percentages)
Sales and marketing

Percentage of total revenue

Year Ended December 31,

2021

2020

Change

$

%

$

183,294 

$

133,225 

$

50,069 

38 %

36 %

36 %

For the year ended December 31, 2021, sales and marketing expense increased by $50.1 million, or 38%, as compared to 2020. This increase was primarily due to increases in
marketing and brand awareness campaigns of $37.1 million, as compared to the same period in 2020, as well as increases in personnel-related costs of $11.1 million.

General and Administrative

(In thousands, except percentages)
General and administrative

Percentage of total revenue

Year Ended December 31,

2021

2020

$

113,081 

$

22 %

71,518 

$

19 %

Change

$

41,563 

%

58 %

For the year ended December 31, 2021, general and administrative expense increased by $41.6 million, or 58%, as compared to 2020. This increase was primarily due to increases
in  personnel-related  costs  of  $29.5  million,  as  compared  to  the  same  period  in  2020,  primarily  because  of  increased  stock-based  compensation  expense  related  to  executive
compensation arrangements. In 2021, we incurred impairment charges of $8.7 million related to certain of our operating lease assets and associated property and equipment.

Provision for Transaction Losses

(In thousands, except percentages)
Provision for transaction losses
Percentage of total revenue

Year Ended December 31,

2021

2020

$

6,048 

$

1 %

3,555 

$

1 %

Change

$

2,493 

%

70 %

For the year ended December 31, 2021, provision for transaction losses increased by $2.5 million, or 70%, as compared to 2020, and represented approximately 1% of revenue for
each period.

62

Interest Expense and Other Income, Net

(In thousands, except percentages)
Interest expense
Other income, net

Year Ended December 31,
2020
2021

Change

$

%

$

2,180  $
(279)

778  $
(469)

1,402 
190 

180 %
(41)%

For  the  year  ended  December  31,  2021,  interest  expense  increased  as  a  result  of  the  issuance  of  the  Notes.  See  “Note  7—Debt”  of  the  notes  to  our  consolidated  financial
statements included elsewhere in this Annual Report for additional information.

Non-GAAP Financial Measures

In addition to our results determined in accordance with U.S. GAAP, adjusted EBITDA is a non-GAAP measure that we believe is useful in evaluating our operating performance.

We define adjusted EBITDA as net income (loss) adjusted for stock-based compensation expense; depreciation and amortization; interest expense; other (income) expense, net;
income tax (benefit) provision; and, if applicable, other non-cash transactions. Adjusted EBITDA is not prepared in accordance with, and is not an alternative to, financial measures
prepared in accordance with U.S. GAAP.

The following table presents a reconciliation of net loss, the most directly comparable financial measure prepared in accordance with U.S. GAAP, to adjusted EBITDA for each of the
periods indicated:

(In thousands)
Net loss
Add back (deduct):

Stock-based compensation expense
Depreciation and amortization
Interest expense
Other income, net
Income tax provision
Tides Foundation common stock warrant expense
Impairment expense

Adjusted EBITDA

2021

Year Ended December 31,
2020

2019

$

(56,240) $

(22,867) $

(16,659)

53,592 
10,261 
2,180 
(279)
122 
750 
8,741 
19,127  $

25,508 
10,172 
778 
(469)
150 
750 
— 
14,022  $

18,798 
6,661 
1,306 
(3,407)
28 
711 
— 
7,438 

$

We use adjusted EBITDA as a measure of operational efficiency. We believe that this non-GAAP financial measure is useful to investors for period-to-period comparisons of our
business and in understanding and evaluating our operating results for the following reasons:

•

•

•

adjusted  EBITDA  is  widely  used  by  investors  and  securities  analysts  to  measure  a  company’s  operating  performance  without  regard  to  items  such  as  stock-based
compensation  expense;  depreciation  and  amortization;  interest  expense;  other  (income)  expense,  net;  income  tax  (benefit)  provision;  and,  if  applicable,  other  non-cash
transactions that can vary substantially from company to company depending upon their financing, capital structures, and the method by which assets were acquired;

our management uses adjusted EBITDA in conjunction with financial measures prepared in accordance with U.S. GAAP for planning purposes, including the preparation of
our annual operating budget, as a measure of our core operating results and the effectiveness of our business strategy, and in evaluating our financial performance; and

adjusted  EBITDA  provides  consistency  and  comparability  with  our  past  financial  performance,  facilitates  period-to-period  comparisons  of  our  core  operating  results,  and
also facilitates comparisons with other peer companies, many of which use similar non-GAAP financial measures to supplement their U.S. GAAP results.

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Our use of adjusted EBITDA has limitations as an analytical tool, and you should not consider it in isolation or as a substitute for analysis of our financial results as reported under
U.S. GAAP. Some of these limitations are as follows:

•

•

•

•

adjusted EBITDA excludes stock-based compensation expense, which has recently been, and will continue to be for the foreseeable future, a significant recurring expense
for our business and an important part of our compensation strategy;

although depreciation and amortization expense are non-cash charges, the assets being depreciated and amortized may have to be replaced in the future, and adjusted
EBITDA does not reflect cash capital expenditure requirements for such replacements or for new capital expenditure requirements;

adjusted EBITDA does not reflect: (a) changes in, or cash requirements for, our working capital needs; (b) interest expense, or the cash requirements necessary to service
interest or principal payments on our debt, which reduces cash available to us; or (c) tax payments that may represent a reduction in cash available to us; and

other companies, including companies in our industry, may calculate adjusted EBITDA or similarly titled measures differently, which reduces the usefulness of this measure
for comparative purposes.

Because of these and other limitations, you should consider adjusted EBITDA along with other financial performance measures, including net loss and our other financial results
prepared in accordance with U.S. GAAP.

Liquidity and Capital Resources

Our principal sources of liquidity are our cash and cash equivalents and marketable securities, including the net proceeds from the sale of the Notes. Our cash equivalents and
marketable securities primarily consist of money market funds, commercial paper, treasury bills, corporate bonds, U.S. government securities, asset-backed securities, and Yankee
bonds. As of December 31, 2021 and 2020, we had $187.2 million and $94.1 million in cash and cash equivalents, respectively. As of December 31, 2021 and 2020, we had $497.6
million and $75.6 million in marketable securities, respectively.

We  believe  our  existing  cash  and  cash  equivalents,  marketable  securities,  and  cash  flow  from  operations  (in  periods  in  which  we  generate  cash  flow  from  operations)  will  be
sufficient for at least the next 12 months to meet our requirements and plans for cash, including meeting our working capital requirements and capital expenditure requirements. In
the long term, our ability to support our working capital and capital expenditure requirements will depend on many factors, including our revenue growth rate, the timing and the
amount of cash received from users, the expansion of sales and marketing activities, the timing and extent of spending to support research and development efforts, the cost to host
our  work  marketplace,  the  introduction  of  new  offerings  and  services,  the  continuing  market  adoption  of  our  work  marketplace,  any  acquisitions  or  investments  that  we  make  in
complementary businesses, products, and technologies and our ability to obtain equity or debt financing. Our principal commitments consist of obligations under our non-cancellable
operating leases for office space and the Notes. As of December 31, 2021, our future lease commitments were $26.5 million (excluding adjustments for discount to present value),
including $6.6 million for 2022. For additional information about our Notes, see the section titled “—Convertible Senior Notes Due 2026.”

We  anticipate  satisfying  our  short-term  cash  requirements  with  our  existing  cash  and  cash  equivalents  and  may  satisfy  our  long-term  cash  requirements  with  cash  and  cash
equivalents  on  hand  or  with  proceeds  from  a  future  equity  or  debt  financing.  To  the  extent  existing  cash  and  cash  equivalents,  cash  from  marketable  securities,  and  cash  from
operations  (in  periods  in  which  we  generate  cash  flow  from  operations)  are  insufficient  to  fund  our  working  capital  and  capital  expenditure  requirements,  or  should  we  require
additional cash for other purposes, we will need to raise additional funds. In the future, we may attempt to raise additional capital through the sale of equity securities or through
equity-linked  or  debt  financing  arrangements,  as  we  did  in  the  third  quarter  of  2021.  If  we  raise  additional  funds  by  issuing  equity  or  equity-linked  securities,  the  ownership  and
economic  interests  of  our  existing  stockholders  will  be  diluted.  If  we  raise  additional  financing  by  incurring  additional  indebtedness,  we  will  be  subject  to  additional  debt  service
requirements  and  could  also  be  subject  to  additional  restrictive  covenants,  such  as  limitations  on  our  ability  to  incur  additional  debt,  and  other  operating  restrictions  that  could
adversely impact our ability to conduct our business. Any future indebtedness we incur may result in terms that could also be unfavorable to our equity investors. There can be no
assurances  that  we  will  be  able  to  raise  additional  capital  on  terms  we  deem  acceptable,  or  at  all.  The  inability  to  raise  additional  capital  as  and  when  required  would  have  an
adverse effect, which could be material, on our results of operations, financial condition, and ability to achieve our business objectives.

64

We also believe that our principal sources of liquidity will allow us to manage the impact of the COVID-19 pandemic on our business operations for the foreseeable future, which
could include reductions in revenue and delays in payments from users, as further described above in “Risk Factors—Our business experienced, and may again experience, an
adverse impact from the ongoing COVID-19 pandemic, including as new variants of COVID-19 emerge. In addition, the positive impacts on our business resulting from the shift to
remote work during the pandemic may not continue as the pandemic subsides and the restrictions intended to prevent its spread are relaxed or lifted.” The challenges posed by the
COVID-19  pandemic  on  our  business  are  expected  to  continue  to  evolve.  Consequently,  we  will  continue  to  evaluate  our  financial  position  in  light  of  future  developments,
particularly those relating to the pandemic.

We  did  not  have  during  the  periods  presented,  and  we  do  not  currently  have,  any  commitments  or  obligations,  including  contingent  obligations,  arising  from  arrangements  with
unconsolidated entities or persons that have or are reasonably likely to have a material current or future effect on our financial condition, changes in financial condition, revenues or
expenses, results of operations, liquidity, cash requirements or capital resources.

Escrow Funding Requirements

As a licensed internet escrow agent, we offer escrow services to users of our work marketplace and, as such, we are required to hold our users’ escrowed cash and in-transit cash
in trust as an asset and record a corresponding liability for escrow funds held on behalf of talent and clients on our balance sheet. We expect the balances of our funds held in
escrow, including funds held in transit, and the related liability to grow as GSV grows and may vary from period to period. Escrow regulations require us to fund the trust with our
operating cash to cover shortages due to the timing of cash receipts from clients for completed hourly billings. Talent submit their billings for hourly contracts to their clients on a
weekly basis every Sunday, and the aggregate amount of such billings is added to escrow funds payable to talent on the same day. As of each Sunday of each week, we have not
yet collected funds for hourly billings from clients as these funds are in transit. Therefore, in order to satisfy escrow funding requirements, every Sunday we fund the shortage of
cash in trust with our own operating cash and typically collect this cash shortage from clients within the next several days. As a result, we expect our total cash and cash flows from
operating activities to be impacted when a quarter ends on a Sunday. As of December 31, 2021 and 2020, funds held in escrow, including funds in transit, were $160.8 million and
$135.0 million, respectively.

Term and Revolving Loans

In August 2021, in connection with our issuance of the Notes, we paid off outstanding amounts under, and terminated, our loan and security agreement with Silicon Valley Bank, as
amended, which we refer to as the Loan Agreement.

Convertible Senior Notes Due 2026

In August 2021, we issued the Notes pursuant to an Indenture between us and Wells Fargo Bank, National Association, as trustee, which we refer to as the Indenture.

The Notes are senior, unsecured obligations and will bear interest at a rate of 0.25% per year, payable semiannually in arrears, and are due August 15, 2026. Upon conversion, we
have an option to pay or deliver, as the case may be, cash, shares of our common stock, or a combination of cash and shares of our common stock. The net proceeds from the
issuance of the Notes were approximately $560.1 million, after deducting debt issuance costs. We used approximately $49.4 million of the net proceeds from the Notes offering to
pay the cost of the Capped Calls. We intend to use the remainder of the net proceeds from the offering for general corporate purposes, including marketing, brand awareness and
sales, and which may include working capital, capital expenditures, and investments in and acquisitions of other companies, products or technologies that we may identify in the
future. See “Note 7—Debt” of the notes to our consolidated financial statements included elsewhere in this Annual Report for additional information regarding the Notes.

Capped Calls

In connection with the issuance of the Notes, we entered into the Capped Calls. The Capped Calls are expected generally to reduce the potential dilution to our common stock upon
any  conversion  of  the  Notes  and/or  offset  any  cash  payments  we  are  required  to  make  in  excess  of  the  principal  amount  of  converted  Notes,  as  the  case  may  be,  with  such
reduction and/or offset subject to a cap based on the cap price.

The initial cap price of the Capped Calls is $92.74 per share of common stock, subject to certain customary adjustments under the terms of the Capped Calls. See “Note 7—Debt”
of the notes to our consolidated financial statements included elsewhere in this Annual Report for additional information regarding the Notes and the Capped Calls.

65

Cash Flows

The following table summarizes our cash flows for the years ended December 31, 2021, 2020, and 2019:

(In thousands)
Net cash provided by operating activities

Net cash used in investing activities

Net cash provided by financing activities

Net change in cash, cash equivalents, and restricted cash

(1)

2021

2020

2019

10,836  $

22,365  $

(428,980)

537,739 

(4,146)

54,641 

119,595  $

72,860  $

1,058 

(100,924)

29,402 

(70,464)

$

$

(1)

 Includes increases in funds held in escrow, including funds in transit of $25.8 million, $26.3 million, and $10.5 million during the years ended December 31, 2021, 2020, and

2019, respectively.

Operating Activities

Our largest source of cash from operating activities is revenue generated from our work marketplace. Our primary uses of cash from operating activities are for personnel-related
expenditures, marketing activities, including advertising, payment processing fees, amounts paid to talent to deliver services for clients under our managed services offering, and
third-party hosting costs. In addition, because we are licensed as an internet escrow agent, our total cash and cash provided by operating activities may be impacted by the timing
of the end of our fiscal quarter as discussed in the section titled “—Liquidity and Capital Resources—Escrow Funding Requirements.”

Net cash provided by operating activities during 2021 was $10.8 million, which resulted from non-cash charges of $83.5 million, offset by a net loss of $56.2 million and net cash
outflows  of  $16.5  million  from  changes  in  operating  assets  and  liabilities.  The  change  in  operating  assets  and  liabilities  primarily  resulted  from  the  increase  in  trade  and  client
receivables. Due to fluctuations in revenue and the number of transactions on our platform, coupled with fluctuations in the timing of cash receipts from clients, our trade and client
receivables will likely continue to fluctuate in the future.

Net cash provided by operating activities during 2020 was $22.4 million, which resulted from non-cash charges of $43.0 million and net cash inflows of $2.2 million from changes in
operating assets and liabilities, offset by a net loss of $22.9 million. The change in operating assets and liabilities primarily resulted from changes in trade and client receivables,
accrued expenses, and other current and long-term liabilities.

Net cash provided by operating activities during 2019 was $1.1 million, which resulted from non-cash charges of $32.2 million, offset by a net loss of $16.7 million and net cash
outflows  of  $14.4  million  from  changes  in  operating  assets  and  liabilities.  The  change  in  operating  assets  and  liabilities  primarily  resulted  from  the  increase  in  trade  and  client
receivables of $10.9 million.

Investing Activities

Net cash used in investing activities during 2021 was $429.0 million, which was primarily a result of investing $525.3 million in various marketable securities, as well as $5.1 million
of internal-use software and platform development costs that we paid during the period and purchases of property and equipment of $1.0 million, partially offset by proceeds from
maturities of marketable securities of $102.5 million.

Net cash used in investing activities during 2020 was $4.1 million, which was primarily a result of investing $107.3 million in various marketable securities during 2020, as well as
$8.0 million of internal-use software and platform development costs that we paid during the period and purchases of property and equipment of $6.3 million primarily for leasehold
improvements and furniture related to our office lease in Chicago, Illinois. These uses of cash were partially offset by proceeds from maturities of marketable securities of $117.5
million.

Net cash used in investing activities during 2019 was $100.9 million, which was primarily a result of investing $168.8 million in various marketable securities during 2019, as well as
$5.9 million of internal-use software and platform development costs that we paid during the period and purchases of property and equipment of $10.8 million primarily for leasehold
improvements and furniture related to our new office leases in Santa Clara, California and Chicago, Illinois. These uses of cash were partially offset by proceeds from maturities of
marketable securities of $84.5 million.

Financing Activities

Net cash provided by financing activities during 2021 was $537.7 million, which resulted primarily from proceeds from the Notes, net of debt issuance costs of $560.1 million, an
increase in escrow funds payable of $25.8 million,

66

cash received from stock option exercises of $7.2 million, and proceeds received from our employee stock purchase plan of $4.8 million, partially offset by purchases of the Capped
Calls of $49.4 million and repayments of borrowings on debt of $10.8 million.

Net cash provided by financing activities during 2020 was $54.6 million, which resulted primarily from cash received from stock option exercises of $31.0 million, proceeds from our
employee stock purchase program of $4.9 million, and an increase in escrow funds payable of $26.3 million, partially offset by net repayments of debt of $7.6 million.

Net cash provided by financing activities during 2019 was $29.4 million, which resulted primarily from cash received from stock option exercises of $18.2 million, proceeds from our
employee stock purchase program of $6.4 million, and an increase in escrow funds payable of $10.5 million, partially offset by net repayments of debt of $5.7 million.

Critical Accounting Policies and Estimates

Our  consolidated  financial  statements  are  prepared  in  accordance  with  U.S.  GAAP.  The  preparation  of  the  consolidated  financial  statements  requires  us  to  make  estimates  and
assumptions that affect the reported amounts of assets, liabilities, revenue, expenses, and related disclosures. We evaluate our estimates and assumptions on an ongoing basis
using historical experience and other factors and adjust those estimates and assumptions when facts and circumstances dictate. Actual results could materially differ from these
estimates and assumptions. Certain of our accounting policies require higher degrees of judgement than others in their application. These include certain aspects of accounting for
revenue recognition, stock-based compensation, and income taxes.

Revenue Recognition

We primarily generate revenue from talent and clients from marketplace and managed service offerings. We account for revenue in accordance with Topic 606, which we adopted
on December 31, 2019 effective as of January 1, 2019 using the modified retrospective method. Revenue is recognized upon transfer of control of promised services to users in an
amount that reflects the consideration we expect to receive in exchange for those services.

Determining the method and amount of revenue to recognize requires management to make judgments and estimates. Judgments include determining whether to present revenue
gross, as a principal, or net, as an agent, which is based on an evaluation of whether we control the service prior to it being transferred to the client, and certain aspects of applying
Topic 606 to our arrangements with talent subject to tiered service fees.

We  apply  judgement  in  the  application  of  the  portfolio  approach  practical  expedient  to  our  arrangements  with  talent  subject  to  tiered  service  fees,  which  includes  estimating  the
standalone selling price of the material rights and the period of time over which to defer and recognize the consideration allocated to the material rights. Specifically, management
applies  judgement  in  assessing  the  continued  appropriateness  for  the  estimates,  which  include  assessing  the  continued  appropriateness  of  the  methodology  and  relevant  data
inputs to estimate the likelihood and the period of time over which to defer and recognize the consideration allocated to the material rights. We utilize historical user transaction data
in developing these estimates. We recognize revenue related to the material rights based on our estimate of when the material rights are exercised, and adjust revenue for changes
in estimates in the period of change on a cumulative catch-up basis.

Stock-Based Compensation

We measure and recognize compensation expense for all stock-based awards granted to service providers, including stock options, RSUs, performance stock units, which we refer
to as PSUs, and purchase rights granted under our 2018 Employee Stock Purchase Plan, which we refer to as the 2018 ESPP, based on the estimated fair value of the award on
the grant date. We calculate the estimated fair value of stock options and purchase rights granted under the 2018 ESPP on the date of grant using the Black-Scholes option pricing
model, which is impacted by the fair value of our common stock, as well as changes in assumptions regarding a number of highly complex and subjective variables. These variables
include, but are not limited to, the expected dividend yield, the expected term of the awards, the risk-free interest rates, and the expected common stock price volatility over the term
of the option awards. The fair value and derived service period of stock options with market-based conditions is estimated using the Monte Carlo valuation model. We evaluate the
assumptions used to value option awards upon each grant of stock options. The grant date fair value of PSUs is determined using the closing common stock price of our common
stock on the grant date multiplied by the number of PSUs that are probable of being earned as of the grant date. We use the quoted market price of our common stock as reported
on The Nasdaq Global Select Market for the fair value of RSUs, PSUs, stock options, and purchase rights under our 2018 ESPP. We generally recognize the fair value of stock
options and RSUs on a straight-line basis over the period during which a service provider is required to provide services in exchange for the award (generally the vesting period).
We recognize the fair value of purchase rights granted under the 2018 ESPP as an expense on a straight-line basis over the offering period and

67

account for forfeitures as they occur. Stock-based compensation expense associated with service- and market-based stock options is recognized over the longer of the expected
achievement  period  for  the  service  condition  and  market  condition.  Stock-based  compensation  expense  associated  with  PSUs  is  recognized  over  the  longer  of  the  expected
achievement period for the performance condition and the service condition.

Income Taxes

We utilize the asset and liability method under which deferred tax assets and liabilities arise from the temporary differences between the tax basis of an asset or liability and its
reported amount in the consolidated financial statements, as well as from net operating loss and tax credit carryforwards. Deferred tax amounts are determined by using the tax
rates expected to be in effect when the taxes will actually be paid or refunds received, as provided for under current tax law. A valuation allowance is established when necessary to
reduce deferred tax assets to the amount expected to be realized. In determining the need for a valuation allowance, we assess, among other things, the historical levels of income
and various sources of taxable income. We regularly review our tax positions and benefits to be realized. We recognize tax liabilities based upon our estimate of whether, and the
extent to which, additional taxes will be due when such estimates are more likely than not to be sustained. An uncertain income tax position will be recognized only if it is more likely
than not to be sustained. We recognize interest and penalties related to income tax matters as income tax expense.

Recent Accounting Pronouncements

See “Note 2—Basis of Presentation and Summary of Significant Accounting Policies” of the notes to our consolidated financial statements included elsewhere in this Annual Report
for recently issued accounting pronouncements not yet adopted as of the date of this Annual Report.

Item 7A. Quantitative and Qualitative Disclosures About Market Risk.

We  have  operations  both  within  the  United  States  and  internationally,  and  we  are  exposed  to  market  risks  in  the  ordinary  course  of  our  business.  These  risks  primarily  include
interest rate and foreign currency exchange rates.

Interest Rate Risk

The primary objective of our investment activities is to preserve principal while maximizing income without significantly increasing risk. We do not make investments for trading or
speculative purposes. Because our cash and cash equivalents have a relatively short maturity, our portfolio’s fair value is relatively insensitive to interest rate changes. Borrowings
under the Notes have a fixed interest rate. Borrowings under the Loan Agreement had variable interest rates. As of December 31, 2021, we had $575.0 million aggregate principal
amount  of  borrowings  outstanding  under  the  Notes.  As  of  December  31,  2020,  we  had  $10.8  million  aggregate  principal  amount  of  borrowings  outstanding  under  our  Loan
Agreement.  We  do  not  believe  that  a  hypothetical  increase  or  decrease  in  interest  rates  of  100  basis  points  would  have  a  material  impact  on  our  operating  results  or  financial
condition.

Foreign Currency Risk

Our operating results and cash flows are subject to fluctuations due to changes in foreign currency exchange rates. In addition to the U.S. dollar, we offer clients the option to settle
invoices denominated in the U.S. dollar in the following currencies: Euro, British Pound, Australian dollar, Canadian dollar, Singapore dollar, South African rand, New Zealand dollar,
Polish  zloty,  Swiss  franc,  Norwegian  krone,  Danish  krone,  Swedish  krona,  Turkish  lira,  Japanese  yen,  and  Hong  Kong  dollar.  When  clients  make  payments  in  one  of  these
currencies, we are exposed to foreign currency risk during the period between when payment is made and when the payment amounts settle. To mitigate this risk, we have entered
into forward contracts. As such, the impact of foreign currency exchange rate fluctuations to our operating results have been insignificant to date.

68

Item 8. Financial Statements and Supplementary Data.

INDEX TO CONSOLIDATED FINANCIAL STATEMENTS

Report of Independent Registered Public Accounting Firm—PCAOB ID: 238

Consolidated Balance Sheets as of December 31, 2021 and 2020

Consolidated Statements of Operations for the Years ended December 31, 2021, 2020, and 2019

Consolidated Statements of Stockholders’ Equity for the Years Ended December 31, 2021, 2020, and 2019

Consolidated Statements of Cash Flows for the Years ended December 31, 2021, 2020, and 2019

Notes to Consolidated Financial Statements

70

73

74

75

76

77

The supplementary financial information required by this item is included in “Management’s Discussion and Analysis of Financial Condition and Results of Operations.”

69

To the Board of Directors and Stockholders of Upwork Inc.

Opinions on the Financial Statements and Internal Control over Financial Reporting

Report of Independent Registered Public Accounting Firm

We  have  audited  the  accompanying  consolidated  balance  sheets  of  Upwork  Inc.  and  its  subsidiaries  (the  “Company”)  as  of  December  31,  2021  and  2020,  and  the  related
consolidated statements of operations, of stockholders' equity and of cash flows for each of the three years in the period ended December 31, 2021, including the related notes
(collectively referred to as the “consolidated financial statements”). We also have audited the Company's internal control over financial reporting as of December 31, 2021, based on
criteria established in Internal Control - Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (COSO).

In our opinion, the consolidated financial statements referred to above present fairly, in all material respects, the financial position of the Company as of December 31, 2021 and
2020,  and  the  results  of  its  operations  and  its  cash  flows  for  each  of  the  three  years  in  the  period  ended  December  31,  2021  in  conformity  with  accounting  principles  generally
accepted in the United States of America. Also in our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of December 31,
2021, based on criteria established in Internal Control - Integrated Framework (2013) issued by the COSO.

Changes in Accounting Principles

As discussed in Note 2 to the consolidated financial statements, the Company changed the manner in which it accounts for revenue from contracts with customers and the manner
in which it accounts for leases in 2019.

Basis for Opinions

The Company's management is responsible for these consolidated financial statements, for maintaining effective internal control over financial reporting, and for its assessment of
the  effectiveness  of  internal  control  over  financial  reporting,  included  in  Management’s  Report  on  Internal  Control  Over  Financial  Reporting  appearing  under  Item  9A.  Our
responsibility is to express opinions on the Company’s consolidated financial statements and on the Company's internal control over financial reporting based on our audits. We are
a public accounting firm registered with the Public Company Accounting Oversight Board (United States) (PCAOB) and are required to be independent with respect to the Company
in accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB.

We  conducted  our  audits  in  accordance  with  the  standards  of  the  PCAOB.  Those  standards  require  that  we  plan  and  perform  the  audits  to  obtain  reasonable  assurance  about
whether the consolidated financial statements are free of material misstatement, whether due to error or fraud, and whether effective internal control over financial reporting was
maintained in all material respects.

Our audits of the consolidated financial statements included performing procedures to assess the risks of material misstatement of the consolidated financial statements, whether
due to error or fraud, and performing procedures that respond to those risks. Such procedures included examining, on a test basis, evidence regarding the amounts and disclosures
in the consolidated financial statements. Our audits also included evaluating the accounting principles used and significant estimates made by management, as well as evaluating
the overall presentation of the consolidated financial statements. Our audit of internal control over financial reporting included obtaining an understanding of internal control over
financial reporting, assessing the risk that a material weakness exists, and testing and evaluating the design and operating effectiveness of internal control based on the assessed
risk. Our audits also included performing such other procedures as we considered necessary in the circumstances. We believe that our audits provide a reasonable basis for our
opinions.

Definition and Limitations of Internal Control over Financial Reporting

A company’s internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of
financial statements for external purposes in accordance with generally accepted accounting principles. A company’s internal control over financial reporting includes those policies
and procedures that (i) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of the assets of the company;
(ii)  provide  reasonable  assurance  that  transactions  are  recorded  as  necessary  to  permit  preparation  of  financial  statements  in  accordance  with  generally  accepted  accounting
principles, and that receipts and expenditures of the company are being made only in accordance with authorizations of management and directors of the company; and (iii) provide
reasonable

70

assurance  regarding  prevention  or  timely  detection  of  unauthorized  acquisition,  use,  or  disposition  of  the  company’s  assets  that  could  have  a  material  effect  on  the  financial
statements.

Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of effectiveness to future
periods  are  subject  to  the  risk  that  controls  may  become  inadequate  because  of  changes  in  conditions,  or  that  the  degree  of  compliance  with  the  policies  or  procedures  may
deteriorate.

Critical Audit Matters

The critical audit matter communicated below is a matter arising from the current period audit of the consolidated financial statements that was communicated or required to be
communicated  to  the  audit  committee  and  that  (i)  relates  to  accounts  or  disclosures  that  are  material  to  the  consolidated  financial  statements  and  (ii)  involved  our  especially
challenging, subjective, or complex judgments. The communication of critical audit matters does not alter in any way our opinion on the consolidated financial statements, taken as
a whole, and we are not, by communicating the critical audit matter below, providing a separate opinion on the critical audit matter or on the accounts or disclosures to which it
relates.

Revenue Recognition – Estimation of Standalone Selling Price of the Talent Material Rights and the Period of Time Over Which to Defer and Recognize the Consideration Allocated
to the Material Rights

As described in Notes 2 and 12 to the consolidated financial statements, the Company charges talent a service fee as a percentage of talent billings primarily using a tiered service
fee model based on cumulative lifetime billings by talent to each client. The Company recorded total revenue of $502.8 million for the year ended December 31, 2021, of which
$297.0  million  related  to  revenue  from  talent.  Certain  of  the  Company’s  contracts  with  talent  contain  multiple  performance  obligations  in  the  event  management  determines  a
material right exists. Specifically, the arrangements with talent subject to tiered service fees include contract renewal options that represent a material right. For such arrangements,
management  allocates  revenue  to  each  performance  obligation  based  on  its  relative  standalone  selling  price  by  applying  the  portfolio  approach  practical  expedient.  Standalone
selling prices for offerings subject to tiered service fees are estimated based on observable transactions when these services are sold on a standalone basis. Standalone selling
price for a material right is estimated by determining the discount that the talent would obtain when exercising the option, adjusted for the likelihood that the option will be exercised.
Management applies significant judgment in the application of the portfolio approach practical expedient, which includes estimating the standalone selling price of the material rights
and the period of time over which to defer and recognize the consideration allocated to the material rights. Specifically, management applied significant judgment in assessing the
appropriateness of the model for the estimates, which includes assessing the appropriateness of the methodology and relevant data inputs to (i) estimate the standalone selling
price of the material rights, which includes the standalone selling price of the services when sold separately and the likelihood of exercise of the material rights, and (ii) estimate the
period of time over which to defer and recognize the consideration allocated to the material rights. Management utilized historical client-talent transaction data in developing the
estimates. The Company recognizes revenue related to the material rights based on management’s estimate of when the material rights are exercised.

The  principal  considerations  for  our  determination  that  performing  procedures  relating  to  revenue  recognition,  specifically  the  estimation  of  standalone  selling  price  of  the  talent
material rights and the period of time over which to defer and recognize the consideration allocated to the material rights, is a critical audit matter are the significant judgment by
management in assessing the appropriateness of the model, methodology and relevant data inputs to estimate the standalone selling price of the material rights, and the period of
time  over  which  to  defer  and  recognize  the  consideration  allocated  to  the  material  rights.  This  in  turn  led  to  significant  auditor  judgment,  subjectivity  and  effort  in  performing
procedures and evaluating audit evidence related to management’s determination of the standalone selling price of the services when sold separately, the likelihood of exercise of
the material rights, and the period of time over which to defer and recognize the consideration allocated to the material rights.

Addressing the matter involved performing procedures and evaluating audit evidence in connection with forming our overall opinion on the consolidated financial statements. These
procedures included testing the effectiveness of controls relating to the revenue recognition process, including the assessment of the appropriateness of the model, methodology
and relevant data inputs to estimate the material rights standalone selling price and the period of time over which to defer and recognize the consideration allocated to the material
rights.  These  procedures  also  included,  among  others,  (i)  evaluating  the  appropriateness  of  management’s  model  used  in  developing  the  estimates,  the  reasonableness  of  the
selected methodology and relevant data inputs used in determining the standalone selling price of the services when sold separately and the likelihood of exercise of the material
rights, and the period of time over which to defer and recognize the consideration allocated to the material rights, (ii)

71

testing the completeness and accuracy of data inputs, and (iii) testing the mathematical accuracy of the model’s calculations and the amounts recorded for the material rights in the
consolidated financial statements.

/s/ PricewaterhouseCoopers LLP

San Jose, California

February 15, 2022

We have served as the Company’s auditor since 2016.

72

2021

2020

UPWORK INC.
CONSOLIDATED BALANCE SHEETS
As of December 31, 2021 and 2020

(In thousands, except share and per share data)
ASSETS
Current assets

Cash and cash equivalents

Marketable securities

Funds held in escrow, including funds in transit

Trade and client receivables – net of allowance of $3,410 and $1,661 as of December 31, 2021 and 2020, respectively

Prepaid expenses and other current assets

Total current assets

Property and equipment, net

Goodwill

Intangible assets, net

Operating lease asset

Other assets, noncurrent

Total assets

LIABILITIES AND STOCKHOLDERS’ EQUITY
Current liabilities

Accounts payable

Escrow funds payable

Debt, current

Accrued expenses and other current liabilities

Deferred revenue

Total current liabilities

Debt, noncurrent

Operating lease liability, noncurrent

Other liabilities, noncurrent

Total liabilities
Commitments and contingencies (Note 6)
Stockholders’ equity

Common stock, $0.0001 par value; 490,000,000 shares authorized as of December 31, 2021 and 2020; 129,130,478 and
124,795,222 shares issued and outstanding as of December 31, 2021 and 2020, respectively

Additional paid-in capital

Accumulated deficit

Total stockholders’ equity

Total liabilities and stockholders’ equity

$

187,205  $

497,566 

160,813 

66,826 

17,243 

929,653 

21,329 

118,219 

— 

10,682 

1,178 

$

$

1,081,061  $

4,996  $

160,813 

— 

45,742 

22,083 

233,634 

561,299 

16,753 

9,858 

821,544 

13 

510,568 

(251,064)

259,517 

The accompanying notes are an integral part of these consolidated financial statements.

$

1,081,061  $

73

94,081 

75,570 

135,042 

47,018 

9,090 

360,801 

28,139 

118,219 

667 

19,729 

1,672 

529,227 

6,455 

135,042 

7,581 

32,868 

16,801 

198,747 

3,142 

20,506 

7,522 

229,917 

12 

494,122 

(194,824)

299,310 

529,227 

UPWORK INC.
CONSOLIDATED STATEMENTS OF OPERATIONS
For the Years Ended December 31, 2021, 2020, and 2019

(In thousands, except per share data)
Revenue
Cost of revenue
Gross profit
Operating expenses

Research and development
Sales and marketing
General and administrative
Provision for transaction losses
Total operating expenses

Loss from operations
Interest expense
Other income, net
Loss before income taxes
Income tax provision
Net loss
Net loss per share, basic and diluted
Weighted-average shares used to compute net loss per share, basic and diluted

$

$
$

2021

2020

2019

502,797  $
135,508 
367,289 

119,083 
183,294 
113,081 
6,048 
421,506 
(54,217)
2,180 
(279)
(56,118)
(122)
(56,240) $
(0.44) $

127,164 

373,628  $
104,267 
269,361 

83,471 
133,225 
71,518 
3,555 
291,769 
(22,408)
778 
(469)
(22,717)
(150)
(22,867) $
(0.19) $

118,699 

300,562 
88,144 
212,418 

64,027 
95,891 
67,327 
3,905 
231,150 
(18,732)
1,306 
(3,407)
(16,631)
(28)
(16,659)
(0.15)
109,815 

The accompanying notes are an integral part of these consolidated financial statements.

74

UPWORK INC.
CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY
For the Years Ended December 31, 2021, 2020, and 2019

(In thousands, except share amounts)
Balances as of December 31, 2018

Cumulative effect adjustment from adoption of new accounting pronouncement
Issuance of common stock upon exercise of stock options and common stock warrants
Stock-based compensation expense
Tides Foundation common stock warrant expense and other
Issuance of common stock for settlement of RSUs
Issuance of common stock in connection with employee stock purchase plan
Net loss

Balances as of December 31, 2019

Issuance of common stock upon exercise of stock options and common stock warrants
Stock-based compensation expense
Tides Foundation common stock warrant expense and other
Issuance of common stock for settlement of RSUs
Issuance of common stock in connection with employee stock purchase plan
Net loss

Balances as of December 31, 2020

Issuance of common stock upon exercise of stock options and common stock warrants
Stock-based compensation expense
Tides Foundation common stock warrant expense and other
Issuance of common stock for settlement of RSUs
Issuance of common stock in connection with employee stock purchase plan
Purchase of capped calls related to convertible senior notes
Net loss

Common Stock

Shares

Amount

106,454,321  $

— 
6,429,471 
— 
— 
163,943 
556,663 
— 
113,604,398 
9,115,947 
— 
— 
1,590,225 
484,652 
— 
124,795,222 
2,085,698 
— 
— 
1,865,444 
384,114 
— 
— 

Additional
Paid-in
Capital

387,233  $

— 
18,155 
18,616 
975 
— 
6,391 
— 
431,370 
31,027 
25,677 
1,135 
— 
4,913 
— 
494,122 
7,176 
53,671 
202 
1 
4,789 
(49,393)
— 

510,568  $

Accumulated
Deficit

Total
Stockholders’
Equity

(143,499) $
(11,799)
— 
— 
— 
— 
— 
(16,659)
(171,957)
— 
— 
— 
— 
— 
(22,867)
(194,824)
— 
— 
— 
— 
— 
— 
(56,240)
(251,064) $

243,745 
(11,799)
18,155 
18,616 
975 
— 
6,391 
(16,659)
259,424 
31,028 
25,677 
1,135 
— 
4,913 
(22,867)
299,310 
7,177 
53,671 
202 
1 
4,789 
(49,393)
(56,240)
259,517 

11  $
— 
— 
— 
— 
— 
— 
— 
11 
1 
— 
— 
— 
— 
— 
12 
1 
— 
— 
— 
— 
— 
— 
13  $

Balances as of December 31, 2021

129,130,478  $

The accompanying notes are an integral part of these consolidated financial statements.

75

UPWORK INC.
CONSOLIDATED STATEMENTS OF CASH FLOWS
For the Years Ended December 31, 2021, 2020, and 2019

(In thousands)
CASH FLOWS FROM OPERATING ACTIVITIES:

Net loss
Adjustments to reconcile net loss to net cash provided by operating activities:
Provision for transaction losses
Depreciation and amortization
Amortization of debt issuance costs
Amortization of premium (accretion of discount) of purchases of marketable securities, net
Amortization of operating lease asset
Tides Foundation common stock warrant expense
Stock-based compensation expense
Impairment expense
Loss on disposal of fixed assets
Changes in operating assets and liabilities:

Trade and client receivables
Prepaid expenses and other assets
Operating lease liability
Accounts payable
Accrued expenses and other liabilities
Deferred revenue

Net cash provided by operating activities
CASH FLOWS FROM INVESTING ACTIVITIES:

Purchases of marketable securities
Proceeds from maturities of marketable securities
Purchases of property and equipment
Internal-use software and platform development costs

Net cash used in investing activities

CASH FLOWS FROM FINANCING ACTIVITIES:

Changes in escrow funds payable
Proceeds from exercises of stock options and common stock warrant
Proceeds from employee stock purchase plan
Proceeds from borrowings on debt
Repayment of debt
Proceeds from issuance of convertible senior notes
Payment of debt issuance costs
Purchases of capped calls related to convertible senior notes

Net cash provided by financing activities

NET CHANGE IN CASH, CASH EQUIVALENTS, AND RESTRICTED CASH
Cash, cash equivalents, and restricted cash—beginning of year

Cash, cash equivalents, and restricted cash—end of year
SUPPLEMENTAL DISCLOSURE OF CASH FLOW INFORMATION:

Cash paid for interest

SUPPLEMENTAL DISCLOSURES OF NON-CASH INVESTING AND FINANCING ACTIVITIES:

Property and equipment purchased but not yet paid
Internal-use software and platform development costs incurred but not yet paid

2021

2020

2019

$

(56,240) $

(22,867) $

(16,659)

5,178 
10,261 
1,182 
298 
3,545 
750 
53,592 
8,741 
— 

(24,610)
(6,960)
(1,163)
(1,445)
10,253 
7,454 
10,836 

(525,343)
102,500 
(1,027)
(5,110)
(428,980)

25,771 
7,177 
4,789 
— 
(10,750)
575,000 
(14,855)
(49,393)
537,739 
119,595 
232,463 
352,058  $

2,919 
10,172 
61 
(320)
3,860 
750 
25,508 
— 
44 

(20,000)
(1,198)
(1,851)
5,822 
15,438 
4,027 
22,365 

(107,281)
117,500 
(6,320)
(8,045)
(4,146)

26,321 
31,028 
4,913 
18,000 
(25,621)
— 
— 
— 
54,641 
72,860 
159,603 
232,463  $

373  $

764  $

22 
106 

37 
286 

3,118 
6,661 
52 
(1,158)
3,945 
711 
18,798 
— 
14 

(10,918)
(2,069)
(1,453)
(1,457)
(2,957)
4,430 
1,058 

(168,786)
84,500 
(10,752)
(5,886)
(100,924)

10,535 
18,155 
6,391 
50,000 
(55,679)
— 
— 
— 
29,402 
(70,464)
230,067 
159,603 

1,291 

161 
684 

$

$

The accompanying notes are an integral part of these consolidated financial statements.

76

UPWORK INC.
Notes to Consolidated Financial Statements

Note 1—Organization and Description of Business

Upwork  Inc.,  which  is  referred  to  as  the  Company  or  Upwork,  operates  a  work  marketplace  that  connects  businesses,  which  are  referred  to  as  clients,  with  independent  talent.
Independent talent on the Company’s work marketplace, which are referred to as talent, and, together with clients, as users, include independent professionals and agencies of
varying sizes and are an increasingly sought-after, critical, and expanding segment of the global workforce. The Company was originally incorporated in the state of Delaware in
December 2013 prior to and in connection with the combination, which is referred to as the Elance-oDesk Combination, of Elance, Inc., which is referred to as Elance, and oDesk
Corporation, which is referred to as oDesk. The Company changed its name to Elance-oDesk, Inc. shortly before the Elance-oDesk Combination in March 2014, and later to Upwork
Inc. The Company is currently headquartered in San Francisco, California.

Unless otherwise expressly stated or the context otherwise requires, the terms “Upwork” and the “Company” in these notes to the consolidated financial statements refer to Upwork
and its wholly-owned subsidiaries.

Note 2—Basis of Presentation and Summary of Significant Accounting Policies

Basis of Presentation and Principles of Consolidation

The accompanying consolidated financial statements have been prepared in accordance with generally accepted accounting principles in the United States, which is referred to as
U.S. GAAP, and include the accounts of Upwork Inc. and its wholly-owned subsidiaries. All intercompany balances and transactions have been eliminated in consolidation.

Use of Estimates

The preparation of the consolidated financial statements in conformity with U.S. GAAP requires management to make certain estimates, judgments, and assumptions that affect the
reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the financial statements, and the reported amounts of revenue and expenses
during the periods presented. Such estimates include, but are not limited to: the useful lives of assets; assessment of the recoverability of long-lived assets; goodwill impairment;
standalone selling price of material rights and the period of time over which to defer and recognize the consideration allocated to the material rights; allowance for doubtful accounts;
liabilities relating to transaction losses; stock-based compensation; and accounting for income taxes. Management bases its estimates on historical experience and on various other
assumptions that management believes to be reasonable under the circumstances. The Company evaluates its estimates, assumptions, and judgments on an ongoing basis using
historical experience and other factors and revises them when facts and circumstances dictate.

Given  the  Company’s  shift  to  a  flexible  work  model  for  its  workforce,  in  2021,  the  Company  subleased  the  entirety  of  its  former  headquarters  in  Santa  Clara,  California  and
subleased a portion of its current headquarters in San Francisco, California. As a result, during the year ended December 31, 2021, the Company incurred impairment charges of
$8.7 million related to the associated operating lease assets and property and equipment. The Company may determine to either close or sublease certain of its other offices, either
of which may result in further impairment charges. See “Note 5—Balance Sheet Components” for additional information regarding these impairments.

Notwithstanding  the  foregoing,  the  Company  is  not  aware  of  any  specific  event  or  circumstance  that  would  require  an  update  to  its  estimates  or  judgments  or  a  revision  of  the
carrying value of its assets or liabilities. These estimates may change as new events occur and additional information is obtained. Actual results could differ materially from these
estimates under different assumptions or conditions.

Cash and Cash Equivalents

The Company classifies as cash and cash equivalents its cash held in checking and interest-bearing accounts and investments in money market funds, U.S. government securities,
and debt securities with maturities of 90 days or less from the date of purchase.

Restricted Cash

As of December 31, 2021 and 2020, the Company maintained restricted cash of $4.0 million and $3.3 million, respectively, related to cash reserve requirements under the escrow
laws and regulations of the California Department of Financial Protection and Innovation and collateral for letters of credit issued in conjunction with operating leases. Short-term
restricted cash included in prepaid expenses and other current assets was $3.2 million

77

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

and  $2.3  million  as  of  December  31,  2021  and  2020,  respectively,  and  long-term  restricted  cash  included  in  other  assets,  noncurrent  was  $0.8  million  and  $1.0  million  as  of
December 31, 2021 and 2020, respectively.

Funds Held in Escrow, Including Funds in Transit

The Company maintains its users’ funds held in escrow in demand or checking accounts at U.S. financial institutions, as well as two California licensed money transmitters. The
balance in these accounts was in excess of federally insured limits as of December 31, 2021 and 2020. Users’ funds held in escrow are denominated exclusively in U.S. dollars.

The Company is an internet escrow agent and is therefore required to hold its users’ escrowed funds and escrow funds in transit in trust as an asset and record a corresponding
liability for escrow funds payable on its consolidated balance sheets. For this reason, funds held in escrow, including funds in transit, are restricted cash. Escrow funds in transit
arise due to the time it takes to clear transactions through external payment networks. When clients fund their escrow account using credit cards, there is a clearing period before
the  cash  is  received  and  settled.  Accordingly,  the  funds  are  treated  as  escrow  funds  in  transit  until  the  transaction is  settled  to  the  escrow  trust  bank  account  or,  in  the  case  of
international  credit  card  settlements,  to  the  Company’s  bank  accounts.  Escrow  regulations  require  the  Company  to  fund  the  trust  with  its  own  operating  cash  if  there  is  ever  a
shortage due to the timing of cash receipts from clients for completed hourly billings. As of December 31, 2021 and 2020, the Company recorded $160.8 million and $135.0 million,
respectively, as funds held in escrow, including funds in transit.

The below table reconciles cash, cash equivalents, and restricted cash as reported in the consolidated balance sheets to the total of the same amounts shown in the consolidated
statements of cash flows for the years ended December 31, 2021, 2020, and 2019:

(In thousands)
Cash and cash equivalents
Restricted cash
Funds held in escrow, including funds in transit

Total cash, cash equivalents, and restricted cash as shown in the consolidated statement of cash flows

Marketable Securities

2021

2020

2019

$

$

187,205  $
4,040 
160,813 
352,058  $

94,081  $
3,340 
135,042 
232,463  $

48,392 
2,490 
108,721 
159,603 

The Company's marketable securities consist of commercial paper, corporate debt securities, treasury bills, U.S. government securities, asset-backed securities, and Yankee debt
securities  issued  by  foreign  governments  or  entities  and  denominated  in  U.S.  dollars,  all  of  which  have  contractual  maturities  within  24  months  from  the  date  of  purchase.  The
marketable securities are available for current operations and are classified as available-for-sale. These marketable securities are carried at estimated fair value with unrealized
gains and losses, net of taxes, included within the stockholders’ equity section of the Company’s consolidated balance sheet.

The Company periodically assesses its portfolio of debt investments for impairment. For debt securities in an unrealized loss position, this assessment first takes into account the
Company’s intent to sell, or whether it is more likely than not that the Company will be required to sell the security before recovery of its amortized cost basis. If either of these
criteria are met, the debt security’s amortized cost basis is written down to fair value through other (income) expense, net. For debt securities in an unrealized loss position that do
not meet the aforementioned criteria, the Company assesses whether the decline in fair value below the amortized cost basis resulted from a credit loss or other factors. In making
this assessment, the Company considers factors such as the extent to which fair value is less than the amortized cost basis, the financial condition of the issuer, any changes to the
rating of the security by a rating agency, and any adverse conditions specifically related to the security, among other factors. If this assessment indicates that a credit loss may exist,
the present value of cash flows expected to be collected from the security are compared to the amortized cost basis of the security. If the present value of cash flows expected to be
collected is less than the amortized cost basis, a credit loss exists and an allowance for credit losses will be recorded through other (income) expense, net, limited by the amount
that the fair value is less than the amortized cost basis. Any additional impairment not recorded through an allowance for credit losses is recognized in other comprehensive loss.
Changes in the allowance for credit losses are reflected as provision for (or reversal of) credit loss expense. Losses are charged against the allowance when management believes
the uncollectability of an available-for-sale security is confirmed or when either of the criteria regarding intent or requirement to sell are met. These changes are recorded in other
income, net. The Company determines realized gains or losses from the sale of marketable securities on a specific identification method and records such gains or losses as other
(income) expense, net within the Company’s consolidated statements of operations.

78

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Escrow Funds Payable

Escrow funds payable represent user funds that are held in escrow by the Company on behalf of both talent and clients. Escrow funds payable to talent are comprised primarily of
funds available to be withdrawn by talent for work performed and paid by clients. Escrow funds payable to clients primarily represent deposits received from certain clients to set up
an account or to apply toward future payments to talent upon completion of the project defined and agreed between the client and talent.

Concentration of Risk

Financial instruments that subject the Company to concentration of risk consist primarily of cash, restricted cash, funds held in escrow, including funds in transit, and trade and client
receivables. The Company maintains its cash balances with large, high-credit quality financial institutions and other payment companies. At times, such deposits may be in excess
of federally insured limits. The Company has not experienced any losses on its deposits. Credit risk on trade receivables is limited as a result of the large size of the Company’s
client base as well as a large portion of payments made using pre-authorized credit cards. The Company performs ongoing credit evaluations of its clients and maintains allowances
for potential credit losses. For any receivables that are deemed not collectible, losses are recorded when probable and estimable. These losses, when incurred, have been within
the range of the Company’s expectations.

One client accounted for more than 10% of trade and client receivables as of December 31, 2021. Three clients each accounted for more than 10% of trade and client receivables
as of December 31, 2020. For the years ended December 31, 2021 and 2020, the Company did not have any clients that accounted for more than 10% of total revenue. For the
year ended December 31, 2019, the Company generated $32.0 million in revenue from one client, which accounted for more than 10% of revenue during the year ended December
31, 2019.

The Company is dependent upon third parties, such as Amazon Web Services, in order to meet the uptime and performance needs of its users.

Fair Value of Financial Instruments

The Company’s financial instruments consist of cash and cash equivalents, restricted cash, funds held in escrow, including funds in transit, marketable securities, trade and client
receivables, prepaid and other current assets, escrow funds payable, and debt.

The Company believes that the carrying values of the remaining financial instruments approximate their fair values.

Trade and Client Receivables and Related Allowance for Doubtful Accounts

Trade and client receivables are primarily comprised of amounts receivable from clients for completed work, including amounts in transit. It also includes unbilled amounts due from
clients  primarily  through  the  Company’s  managed  services  offering.  Trade  and  client  receivables  are  recorded  and  stated  at  realizable  value,  net  of  an  allowance  for  doubtful
accounts.  Credit  is  extended  generally  without  collateral  to  the  Company’s  managed  services  and  marketplace  clients  with  Upwork  Enterprise  offerings  based  on  an  initial  and
ongoing evaluation of their financial condition and other factors. In aggregate, gross trade receivables were $19.7 million and $15.9 million and gross client receivables were $50.5
million and $32.8 million as of December 31, 2021 and 2020, respectively.

The allowance for doubtful accounts is the Company’s estimate of the probable credit losses on accounts receivable. The Company periodically assesses the collectability of the
accounts  and  determines  the  allowance  recognized  by  taking  into  consideration  the  aging  of  its  receivable  balances,  historical  write-off  experience,  probability  of  collection,  and
other  relevant  data.  Trade  and  client  receivables  are  written  off  against  the  allowance  when  management  determines  a  balance  is  uncollectible  and  no  longer  actively  pursues
collection of the receivable.

79

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

The following table presents the changes in the allowance for doubtful accounts as of December 31, 2021, 2020, and 2019:

(In thousands)
Allowance for doubtful accounts, beginning balance
Provision for doubtful accounts
Amounts written off

Allowance for doubtful accounts, ending balance

Derivative Instruments

2021

2020

2019

$

$

1,661  $
4,803 
(3,054)
3,410  $

2,215  $
3,143 
(3,697)
1,661  $

2,832 
3,193 
(3,810)
2,215 

The Company uses derivative financial instruments not designated as hedges, such as foreign currency forward contracts, to minimize the short-term impact of foreign currency
exchange rate fluctuations on certain foreign currency denominated assets and liabilities, as well as certain foreign currency denominated expenses, hedging the gains or losses
generated  by  the  re-measurement  of  significant  foreign  currency  denominated  monetary  assets  and  liabilities.  The  Company  does  not  enter  into  derivative  instruments  for
speculative or trading purposes and these instruments generally have maturities within 12 months.

The foreign currency forward contracts are recorded at fair value and, when in gain positions, are reported within prepaid expenses and other current assets. When in loss positions,
the foreign currency forward contracts are recorded within accrued expenses and other current liabilities in the consolidated balance sheets. Gains or losses from changes in the fair
value of these foreign currency forward contracts not designated as hedging instruments are recorded in other income, net to offset the changes in the fair value of the underlying
assets or liabilities being hedged.

The notional amounts associated with the Company’s foreign currency forward contracts at December 31, 2021 and 2020 were $7.2 million and $7.6 million, respectively, none of
which were designated as cash flow hedges. The carrying values of the foreign currency forward contracts approximated their fair values due to their relatively short settlement
durations. The fair values of the Company’s outstanding foreign currency forward contracts not designated as hedging instruments as of December 31, 2021 and 2020 were not
material. Losses on foreign currency forward contracts not designated as hedging instruments were $0.5 million for the year ended December 31, 2021. Losses on foreign currency
forward contracts not designated as hedging instruments were $0.6 million for the year ended December 31, 2020. Gains on foreign currency forward contracts not designated as
hedging instruments were $0.9 million for the year ended December 31, 2019.

Leases

The Company accounts for leases in accordance with Financial Accounting Standards Board, which is referred to as the FASB, Accounting Standards Update, which is referred to
as ASU, No. 2016-02, Leases (Topic 842), which the Company adopted on December 31, 2019 effective as of January 1, 2019 using the effective date method.

Property and Equipment

Property and equipment are stated at cost, net of accumulated depreciation and amortization. Depreciation is calculated using the straight-line method over the estimated useful
lives of the related assets, which are generally two to five years. Leasehold improvements are amortized on a straight-line basis over the shorter of the remaining lease term or their
estimated useful lives. Repair and maintenance costs are charged to expense as incurred.

Internal-Use Software and Platform Development Costs

The  Company’s  policy  is  to  capitalize  certain  costs  to  develop  its  internal-use  software  and  platform  when  (i)  preliminary  project  planning  is  completed,  (ii)  the  Company  has
committed project resourcing, and (iii) it is probable that the project will be completed and the software will be used as intended. Costs incurred for enhancements that are expected
to  result  in  additional  significant  functionality  are  also  capitalized.  Such  costs  are  generally  amortized  on  a  straight-line  basis  over  their  estimated  useful  lives  determined  on  a
project-by-project basis, which historically has ranged between two to three years, beginning when the asset is ready for its intended use. Costs incurred prior to meeting these
criteria, together with costs incurred for training and maintenance, are expensed as incurred. Amortization of capitalized internal-use software and platform development costs is
allocated to functional expense categories based on headcount and the nature and intended use of the project.

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UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Segment Information

The Company has one reportable segment. The Company’s chief operating decision maker is its President and Chief Executive Officer, who reviews financial information presented
on a consolidated basis for purposes of allocating resources and evaluating financial performance.

Goodwill, Acquired Intangible Assets, and Other Long-Lived Assets

Goodwill represents the excess of the aggregate fair value of the consideration transferred over the fair value of the net tangible and identifiable intangible assets acquired in the
Elance-oDesk Combination. Goodwill is not amortized, but rather is assessed for impairment at least annually, or more frequently if events and changes in circumstances indicate
that  its  carrying  amount  may  not  be  recoverable.  The  Company  performs  its  annual  impairment  assessment  during  the  fourth  quarter  of  each  calendar  year  based  on  a  single
reporting unit structure by comparing the carrying value of the reporting unit to its fair value. An impairment would occur if the carrying amount of a reporting unit exceeded the fair
value of that reporting unit. There has been no impairment of goodwill for any of the periods presented.

The Company’s long-lived assets consist of property and equipment and acquired identifiable, finite-lived intangible assets, namely developed technology, user relationships, trade
names, and domain names. The finite-lived intangible assets are carried at cost, less accumulated amortization. The Company amortizes the finite-lived intangible assets over their
estimated useful lives ranging from two to seven years based on the pattern in which the economic benefits of the intangible assets are consumed, or the straight-line method when
the pattern cannot be reliably determined. The Company periodically reviews the remaining estimated useful lives of its long-lived tangible and amortizable intangible assets. If the
estimated  useful  life  assumption  for  any  asset  is  changed,  the  remaining  unamortized  balance  would  be  depreciated  or  amortized  over  the  revised  estimated  useful  life,  on  a
prospective basis. Intangible amortization expense related to developed technology and trade names is recorded as cost of revenue. Intangible amortization expense related to user
relationships and domain names is included in operating expenses.

The Company evaluates the recoverability of its long-lived assets, including finite-lived intangible assets, for possible impairment whenever events or circumstances indicate that the
carrying amount of such assets may not be recoverable. Recoverability of these assets is measured by comparing the carrying amounts to the future undiscounted cash flows the
assets are expected to generate. If it is determined that the asset group is not recoverable, an impairment loss is recorded in the amount by which the carrying amount of the asset
group exceeds the aggregate future undiscounted cash flows. When an impairment loss is recognized, the carrying amount of such assets is reduced to fair value.

For 2021, the Company conducted its goodwill impairment testing by performing the first step of the two-step impairment model. The fair value was determined by the Company
using  quoted  market  prices  of  the  Company’s  common  stock.  The  Company  determined  that  the  fair  value  of  its  reporting  unit  exceeded  the  carrying  value,  and,  as  such,  the
Company concluded that there was no impairment of goodwill at the impairment testing date.

There was no impairment of long-lived assets in any of the periods presented.

Convertible Senior Notes

The Company accounts for its convertible senior notes, which are referred to as the Notes, as a single liability measured at amortized cost. The carrying value of the liability equals
the proceeds received from the issuance of the Notes less debt issuance costs. See “Note 7—Debt” for additional information.

Debt Issuance Costs

Debt  issuance  costs  incurred  in  connection  with  securing  the  Company’s  financing  arrangements  are  capitalized  and  amortized  over  the  term  of  the  respective  financing
arrangement  under  the  straight-line  method  as  the  results  obtained  are  not  materially  different  from  those  that  would  result  from  the  use  of  the  effective  interest  method.  Debt
issuance costs are generally presented in the Company’s consolidated balance sheets as a reduction to the carrying amount of the outstanding borrowings.

Revenue Recognition

The  Company  primarily  generates  revenue  from  clients  from  its  marketplace  and  managed  service  offerings  and  from  talent  from  its  marketplace.  The  Company  accounts  for
revenue  in  accordance  with  FASB  ASU  No.  2014-09,  Revenue  from  Contracts  with  Customers (Topic  606),  which  the  Company  adopted  on  December  31,  2019  effective  as  of
January 1, 2019 using the modified retrospective method. Revenue is recognized upon transfer of control of

81

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

promised services to users in an amount that reflects the consideration the Company expects to receive in exchange for those services.

In the ordinary course of business, the Company makes payments to users when those users provide services in their capacity as vendors. These payments are for distinct services
and  are  at  fair  value.  These  transactions  are  primarily  with  certain  financial  institutions  that  the  Company  uses  as  payment  processors  on  the  work  marketplace.  The  Company
accounts for the consideration payable to these users in their capacity as vendors as a purchase of services from a vendor and records such payments in either cost of revenue or
sales and marketing within the consolidated statements of operations.

Marketplace Offerings

The Company’s marketplace revenue, which represents the majority of its revenue, consists primarily of revenue derived from Upwork Basic, Plus, and Enterprise offerings. The
Company generates marketplace revenue from both talent and clients. Revenue from the Company’s Upwork Basic and Plus offerings are primarily comprised of talent service fees,
and to a lesser extent, payment processing and administration fees charged to clients. Revenue from the Company’s Upwork Enterprise offering, which is referred to as Enterprise
Revenue,  includes  all  client  fees,  subscriptions,  and  talent  service  fees.  The  Company  also  generates  marketplace  revenue  from  fees  for  premium  offerings  associated  with  its
Upwork Basic, Plus, and Enterprise offerings, including talent memberships, purchases of Connects, and other services, such as foreign currency exchange when clients choose to
pay in currencies other than the U.S. dollar, and the Company’s Upwork Payroll offering.

Upwork Basic, Plus, and Other Premium Offerings

The Company earns fees from talent under the Upwork Basic, Plus, and associated premium offerings, which represent a single promise to provide continuous access (i.e. stand-
ready performance obligation) to the Company’s work marketplace and site services. As each day of providing access to the work marketplace and site services (including, but not
limited to, communication, invoicing, reporting, dispute resolution, and payment services) is substantially the same and talent simultaneously receive and consume the benefits as
access is provided, the Company’s single promise under its Upwork Basic and Plus offerings is comprised of a series of distinct service periods. The Company allocates variable
consideration  to  each  distinct  service  period  in  which  it  has  the  contractual  right  to  bill.  The  Company’s  Upwork  Basic  and  Plus  arrangements  may  include  fixed  and  variable
consideration, or a combination of the two, comprised of the following:

Service  fees.  Talent  are  provided  access  to  the  Upwork  work  marketplace  to  market  their  businesses,  send  proposals  to  and  communicate  with  prospective  clients,  and,  if
engaged by a client, to perform specified services agreed between talent and clients, which are referred to as talent services. Talent charge clients on an hourly or a milestone
basis for services rendered to clients through the Upwork work marketplace, which are referred to as talent billings. The Company charges talent a service fee as a percentage
of talent billings primarily using a tiered service fee model based on cumulative lifetime billings by talent to each client. The arrangements subject to tiered service fees also
include  contract  renewal  options  that  represent  a  material  right.  The  Company  takes  no  responsibility  for  talent  services,  and  therefore,  does  not  control  talent  services.
Additionally,  talent  and  clients  negotiate  and  agree  upon  the  scope  and  the  price  for  talent  services  directly  with  each  other,  and  the  Company  is  not  a  party  to  those
agreements. Accordingly, for these tiered service fee arrangements, the Company presents revenue on a net basis, as an agent. The Company recognizes the service fees for
each distinct service period when it has the contractual right to bill for the services.

Withdrawal  fees.  The  Company  charges  withdrawal  fees  to  talent  when  talent  withdraw  their  escrow  funds  held  by  the  Company.  A  withdrawal  fee  is  charged  for  each
withdrawal transaction, which represents variable consideration. The Company presents revenue from withdrawal fees on a gross basis as a principal and not net of the third-
party payment processing costs incurred because the Company controls the payment processing services prior to providing to the Company's talent. The Company recognizes
the withdrawal fees when transactions are processed, which is when it has the contractual right to bill for the services.

Membership fees. The Company charges membership fees to talent. These fees are fixed consideration and are charged monthly. The Company recognizes the revenue over
the period of the membership, which is generally monthly, consistent with the common measure of progress for the entire performance obligation.

Connects fees. The Company charges fees to talent for the purchase of Connects, which are virtual tokens that are required for talent to bid on projects on the Company’s work
marketplace. These fees represent variable consideration and are allocated to and recognized in the distinct service period in which the Connects are used.

82

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

The Company earns fees from clients under the Upwork Basic and Plus offerings, which represent a single promise to provide continuous access (i.e. stand-ready performance
obligation) to the Company’s work marketplace and site services. As each day of providing access to the work marketplace and site services is substantially the same and the client
simultaneously receives and consumes the benefits as access is provided, the Company’s single promise under its Upwork Basic and Plus offerings is comprised of a series of
distinct service periods. The Company allocates variable consideration to each distinct service period in which it has the contractual right to bill. The Company’s Upwork Basic and
Plus arrangements may include fixed and variable consideration, or a combination of the two, comprised of the following:

Client payment processing and administration fees. The Company charges clients for payment processing services at the time the client is charged for the amounts due from
the client. This fee is charged on a per-transaction basis and is variable consideration. Per-transaction payment processing fees are recognized when the client is charged for
the amount due and fees charged on a monthly basis are recognized over the month that payment processing services are provided. For client payment processing fees, the
Company  presents  revenue  on  a  gross  basis  as  a  principal  and  not  net  of  the  third-party  payment  processing  costs  incurred  because  the  Company  controls  the  payment
processing and administration services prior to providing to the Company’s clients. The Company recognizes the revenue when a payment from a client is processed, which is
when it has the contractual right to bill for the services.

Foreign currency exchange fees. The Company charges clients a fixed mark-up above foreign currency exchange rates that are charged to the Company when the Company
collects  amounts  denominated  in  foreign  currency.  Foreign  currency  exchange  fees  are  variable  consideration  and  recognized  as  they  are  earned  for  each  transaction
processed, which is when the Company has the contractual right to bill for the services.

Membership fees.  The  Company  charges  membership  fees  to  clients.  These  fees  are  charged  monthly,  are  fixed  consideration,  and  are  recognized  over  the  period  of  the
membership, which is generally monthly consistent with the common measure of progress for the entire performance obligation.

Upwork Payroll service fees. The Company charges clients using the Upwork Payroll offering when their talent are classified as employees for engagements on the Upwork
work  marketplace.  The  client  enters  into  an  Upwork  Payroll  agreement  with  the  Company,  and  Upwork  separately  contracts  with  unrelated  third-party  staffing  providers  that
provide  employment  services  to  such  clients.  In  such  arrangements,  talent  providing  talent  services  to  clients  become  employees  of  third-party  staffing  providers.  In
arrangements where clients enter into Upwork Payroll agreements, the Company charges Upwork Payroll service fees to clients and does not charge service fees to talent who
are employees of the third-party staffing providers. Such service fees are variable consideration and charged as a fixed percentage of the total talent billings. Under an Upwork
Payroll agreement, the Company provides the client access to the Upwork work marketplace to procure and manage talent services, as well as access to employment services
provided  by  the  third-party  staffing  providers.  The  Company  presents  Upwork  Payroll  service  fees  revenue  on  a  net  basis  as  an  agent  of  the  client  for  providing  access  to
employment  services  provided  by  the  third-party  staffing  providers.  The  Company  does  not  control  these  employment  services  performed  by  the  third-party  on  behalf  of  the
client or for the services performed by talent that are employed by the third-party staffing providers. Therefore, the Company is not considered the principal for these services.
The Company recognizes the service fees for each distinct service period when it has the contractual right to bill for the services.

Upwork Enterprise and Other Premium Offerings

The Company earns fees from talent under Upwork Enterprise and other associated premium offerings, each of which represent a single promise to provide continuous access (i.e.
stand-ready  performance  obligation)  to  the  Company’s  work  marketplace  and  site  services.  As  each  day  of  providing  access  to  the  work  marketplace  and  site  services  is
substantially the same and talent simultaneously receive and consume the benefits as access is provided, the Company’s single promise under its Upwork Enterprise and other
premium offerings is comprised of a series of distinct service periods. The Company allocates variable consideration to each distinct service period in which it has the contractual
right to bill. These arrangements include variable consideration as follows:

Service fees.  The  Company  provides  talent  access  to  the  Upwork  work  marketplace  to  perform  talent  services  for  clients.  The  Company  charges  talent  a  service  fee  as  a
percentage of talent billings. The Company earns service fees based on a fixed percentage of talent billings. For service fees charged to talent, the Company presents revenue
on a net basis, as an agent, for providing access to the Upwork work marketplace as it does not control talent services provided to clients, and therefore the Company is not
considered the principal for talent services. Additionally, talent and clients negotiate and agree upon the scope and the price for talent

83

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

services directly with each other, and the Company is not a party to their agreement. The Company recognizes the service fees for each distinct service period in which it has
the contractual right to bill for the services.

The Company earns fees from clients under Upwork Enterprise and other premium offerings, each of which represent a single promise to provide continuous access (i.e. stand-
ready performance obligation) to the Company’s work marketplace and site services. As each day of providing access to the work marketplace and site services is substantially the
same  and  the  client  simultaneously  receives  and  consumes  the  benefits  as  access  is  provided,  the  Company’s  single  promise  under  its  Upwork  Enterprise  and  other  premium
offerings is comprised of a series of distinct service periods. The Company allocates variable consideration to each distinct service period in which it has the contractual right to bill.
These arrangements may include fixed and variable consideration, or a combination of the two, comprised of the following:

Client service fees. The Company offers clients access to the Company’s work marketplace to source talent in exchange for a client service fee calculated as a percentage of
talent billings; these fees represent variable consideration. The Company recognizes the service fees for each distinct service period in which it has the contractual right to bill
for the services.

Enterprise compliance service fees. The Company charges fees to its enterprise compliance service clients that engage the Company to provide services to determine whether
talent  should  be  classified  as  an  employee  or  an  independent  contractor  based  on  the  scope  of  talent  services  agreed  between  the  client  and  talent  and  other  factors.  The
Company charges enterprise compliance service fees as a percentage of talent billings; these fees represent variable consideration. The Company recognizes the service fees
for each distinct service period in which it has the contractual right to bill for the services.

Subscription fees.  The  Company  charges  monthly  or  annual  subscription  fees  to  clients  for  subscription  services.  These  subscription  fees  are  fixed  consideration  and  are
recognized over the period of the subscription consistent with the common measure of progress for the entire performance obligation.

Upwork  Payroll  service  fees.  Upwork  Payroll  service  fees  are  recognized  on  the  same  basis  as  described  under  the  Upwork  Basic  and  Plus  offerings  and  are  variable
consideration.

Revenue sharing arrangements

Certain of the Company’s offerings include revenue sharing arrangements under which the Company generates a revenue share as a percentage of the fees charged by certain
financial institutions to talent for payment withdrawals. These arrangements are considered a single performance obligation comprised of variable consideration and are recognized
over time based on transactions processed.

Managed Services

Under a managed services arrangement, the Company is responsible for providing services and engaging talent directly or as employees of third-party staffing providers to perform
the services for clients on the Company’s behalf. These arrangements are generally time- and materials-based, and are invoiced on a monthly basis. These fees represent variable
consideration. The Company controls and directs the services performed on behalf of talent and presents revenue on a gross basis as principal. As each day of providing managed
services is substantially the same and the client simultaneously receives and consumes the benefits as services are provided, the Company’s single promise under its managed
services is comprised of a series of distinct service periods. For managed services arrangements with clients, the Company allocates the variable amounts to each distinct service
period within the series in which it has the contractual right to bill and recognizes revenue as each distinct service period is performed.

Arrangements with Multiple Performance Obligations

Certain of the Company’s contracts with talent contain multiple performance obligations in the event the Company determines a material right exists. Specifically, the arrangements
with  talent  subject  to  tiered  service  fees  include  contract  renewal  options  that  represent  a  material  right.  For  such  arrangements,  the  Company  allocates  revenue  to  each
performance obligation based on its relative standalone selling price by applying the portfolio approach practical expedient under Topic 606. Standalone selling prices for offerings
subject to tiered service fees are estimated based on observable transactions when these services are sold on a standalone basis. Standalone selling price for a material right is
estimated by determining the discount that talent would obtain when exercising the option, adjusted for the likelihood that the option will be exercised. Significant judgment is applied
in the application of the portfolio approach practical expedient, which includes estimating the standalone selling price of the material rights and the period of time over which to defer
and recognize the consideration allocated to the material rights. Specifically, management applied significant judgment in assessing the appropriateness of the

84

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

model for the estimates, which include assessing the appropriateness of the methodology and relevant data inputs to (i) estimate the standalone selling price of the material rights,
which includes the standalone selling price of the services when sold separately and the likelihood of exercise of the material rights; and (ii) estimate the period of time over which to
defer and recognize the consideration allocated to the material rights. The Company utilized historical user transaction data in developing the estimates. The Company recognizes
revenue related to the material rights based on the Company’s estimate of when the material rights are exercised and adjusts revenue for changes in estimates in the period of
change on a cumulative catch-up basis.

Deferred Revenue

Deferred  revenue  consists  of  subscription,  membership,  and  Connects  fees  collected  in  advance  of  performing  the  service.  The  Company  also  recognizes  deferred  revenue  for
amounts attributable to unexercised material rights related to arrangements with talent that are subject to tiered service fees.

Cost of Revenue

Cost of revenue consists primarily of the cost of payment processing fees, costs of talent to deliver services under the Company’s managed services offering, personnel-related
costs  for  the  Company’s  services  and  support  personnel,  third-party  hosting  fees,  and  amortization  expense  associated  with  acquired  intangibles  and  capitalized  internal-use
software.  The  Company  defines  personnel-related  costs  as  salaries,  bonuses,  benefits,  and  stock-based  compensation  costs  for  employees,  and  costs  related  to  other  service
providers the Company engages to provide internal services to the Company.

Research and Development

Research and development expense primarily consists of personnel-related costs. Research and development costs are expensed as incurred, except to the extent that such costs
are associated with internal-use software and platform development that qualify for capitalization.

Advertising Expense

The  Company  expenses  advertising  costs  as  incurred.  The  Company  incurred  $90.8  million,  $51.4  million,  and  $37.4  million  in  advertising  expenses  during  the  years  ended
December 31, 2021, 2020, and 2019, respectively.

Provision for Transaction Losses

Provision for transaction losses consists primarily of losses resulting from fraud on the work marketplace and bad debt expense associated with the Company’s trade and client
receivables  balance  and  transaction  losses  expense  related  to  chargebacks.  Provision  for  these  items  represents  estimates  of  losses  based  on  the  Company’s  actual  historical
incurred losses and other factors.

Stock-Based Compensation

The  Company  accounts  for  stock  options  with  service-  and  market-based  conditions,  restricted  stock  units,  which  are  referred  to  as  RSUs,  performance  stock  units,  which  are
referred to as PSUs, and purchase rights granted under the 2018 Employee Stock Purchase Plan, which is referred to as the 2018 ESPP, to employees and directors based on their
estimated  fair  value  on  the  date  of  grant.  The  fair  value  and  derived  service  period  of  stock  options  with  market-based  conditions  is  estimated  using  the  Monte  Carlo  valuation
model. The Company evaluates the assumptions used to value option awards upon each grant of stock options. The fair value of RSUs awarded to employees is based on the
closing price of the Company’s common stock, as reported on The Nasdaq Global Select Market on the date of grant. The grant date fair value of PSUs is determined using the
Company’s closing common stock price on the grant date multiplied by the number of PSUs that are probable of being earned as of the grant date. The fair value of purchase rights
granted under the 2018 ESPP is estimated using the Black-Scholes valuation model. The model requires the Company to make a number of assumptions, including the value of the
Company’s common stock, expected volatility, expected term, risk-free interest rate, and expected dividends.

Stock-based compensation expense associated with service- and market-based stock options will be recognized over the longer of the expected achievement period for the service
condition  and  market  condition.  The  Company  generally  recognizes  stock-based  compensation  expense  for  RSUs  on  a  straight-line  basis  over  the  vesting  term.  Stock-based
compensation expense associated with PSUs is recognized over the longer of the expected achievement period for the performance condition and the service condition. Stock-
based compensation for purchase rights granted under the 2018 ESPP is recognized over the offering period. The Company accounts for forfeitures as they occur.

85

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Foreign Currency

The functional currency of the Company and its subsidiaries is the U.S. dollar. Transactions with users denominated in currencies other than the U.S. dollar are remeasured at the
exchange rate in effect on the date of the transaction. At the end of each reporting period, monetary assets and liabilities are remeasured using exchange rates in effect at the
balance  sheet  date.  Foreign  currency  transaction  gains  and  losses  are  included  in  other  income,  net  in  the  consolidated  statements  of  operations.  The  Company  recorded  net
foreign currency transaction losses of $0.5 million for the year ended December 31, 2021, net foreign currency transaction losses of $0.6 million for the year ended December 31,
2020, and net foreign currency transaction gains of $0.9 million for the year ended December 31, 2019.

Comprehensive Loss

For the years ended December 31, 2021, 2020, and 2019, net unrealized losses from the Company’s marketable securities were immaterial. Comprehensive loss approximates net
loss for all periods presented. Accordingly, the consolidated statements of comprehensive loss have been omitted from the consolidated financial statements.

Income Taxes

The Company accounts for income taxes in accordance with the asset and liability method. Under the asset and liability method, deferred assets and liabilities are recognized based
upon  anticipated  future  tax  consequences  attributable  to  differences  between  financial  statement  carrying  amounts  of  assets  and  liabilities  and  their  respective  tax  bases.  The
provision for income taxes is comprised of the current tax liability and the change in deferred tax assets and liabilities. The Company establishes a valuation allowance to the extent
that it is more likely than not that deferred tax assets will not be recoverable against future taxable income.

Deferred tax assets and liabilities are measured using the enacted tax rates that will be in effect for the years in which those tax assets are expected to be realized or settled. The
Company  regularly  assesses  the  likelihood  that  its  deferred  tax  assets  will  be  realized  from  recoverable  income  taxes  or  recovered  from  future  taxable  income  based  on  the
realization criteria set forth in the relevant authoritative guidance. To the extent that the Company believes any amounts are not more likely than not to be realized, the Company
records a valuation allowance to reduce its deferred tax assets. The realization of deferred tax assets is dependent upon future earnings, if any, the timing and amount of which are
uncertain. Accordingly, the net deferred tax assets have been fully offset by a valuation allowance. If the Company subsequently realizes deferred tax assets that were previously
determined to be unrealizable, the respective valuation allowance would be reversed, resulting in an adjustment to earnings in the period such determination is made.

In addition, the calculation of tax liabilities involved dealing with uncertainties in the application of complex tax regulations. The Company recognized potential liabilities based on its
estimate  of  whether,  and  the  extent  to  which,  additional  taxes  will  be  due.  The  Company  accounts  for  uncertain  tax  positions  in  accordance  with  the  relevant  guidance,  which
prescribes  a  recognition  threshold  and  measurement  approach  for  uncertain  tax  positions  taken  or  expected  to  be  taken  in  a  company’s  income  tax  return,  and  also  provides
guidance  on  recognition,  classification,  interest  and  penalties,  accounting  in  interim  periods,  disclosure,  and  transition.  The  guidance  utilized  a  two-step  approach  for  evaluation
uncertain tax positions. Step one, Recognition, requires a company to determine if the weight of available evidence indicates a tax position is more likely than not to be sustained
upon  audit.  Step  two,  Measurement,  is  based  on  the  largest  amount  of  benefit,  which  is  more  likely  than  not  to  be  realized  on  ultimate  settlement.  A  liability  is  reported  for
unrecognized tax benefits resulting from uncertain tax positions taken or expected to be taken in a tax return. Any interest and penalties related to unrecognized tax benefits are
recorded as income tax expense.

Net Loss per Share

Basic  net  loss  per  share  is  computed  by  dividing  the  net  loss  by  the  weighted-average  number  of  common  shares  outstanding  for  the  period.  Diluted  net  loss  is  computed  by
adjusting net loss to reallocate undistributed earnings based on the potential impact of dilutive securities, including outstanding common stock options, RSUs, PSUs, warrants to
purchase common stock, common stock issuable in connection with the 2018 ESPP, and common stock issuable in connection with the Notes. For periods in which the Company
has reported net losses, diluted net loss per share is the same as basic net loss per share because dilutive common shares are not assumed to have been issued if their effect is
anti-dilutive.

Recent Accounting Pronouncements Not Yet Adopted

The  Company  has  reviewed  all  recently  issued  accounting  pronouncements  and  concluded  they  were  either  not  applicable  or  not  expected  to  have  a  material  impact  on  the
Company’s consolidated financial statements.

86

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Recently Adopted Accounting Pronouncements

In  December  2019,  the  FASB  issued  ASU  No.  2019—12  (Topic  740),  Simplifying  the  Accounting  for  Income  Taxes.  This  guidance  simplifies  accounting  for  income  taxes  by
removing certain exceptions to the general principles and amending existing guidance to improve consistent application. The Company is required to adopt this guidance in the year
ended December 31, 2021. The Company concluded that there was not a material impact to its consolidated financial statements as a result of the adoption.

In August 2020, the FASB issued ASU No. 2020—06, Debt—Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging—Contracts in Entity’s Own
Equity (Subtopic 815-40): Accounting for Convertible Instruments and Contracts in an Entity’s Own Equity, which simplifies the accounting for convertible instruments by reducing
the  number  of  accounting  models  available  for  convertible  instruments.  This  guidance  also  eliminates  the  treasury  stock  method  to  calculate  diluted  earnings  per  share  for
convertible instruments and requires the use of the if-converted method. For public companies, this guidance is effective for fiscal years beginning after December 15, 2021 and
interim periods within those fiscal years. Early adoption is permitted. The Company early adopted the standard as of January 1, 2021 and applied this guidance to the Notes issued
in August 2021. Refer to “Note 7—Debt” for additional information.

Note 3—Revenue

Disaggregation of Revenue

See Note 12 for the Company’s revenue disaggregated by type of service and geographic area.

Remaining Performance Obligations

As  of  December  31,  2021,  the  Company  had  approximately  $28.4  million  of  remaining  performance  obligations.  The  Company’s  remaining  performance  obligations  consist  of
transaction  price  that  has  been  allocated  to  unexercised  material  rights  related  to  the  Company’s  arrangements  with  talent  subject  to  tiered  service  fees,  subscriptions,
memberships,  and  Connects.  As  of  December  31,  2021,  the  Company  expects  to  recognize  approximately  $22.1  million  over  the  next  12  months,  with  the  remaining  balance
recognized thereafter.

The Company has applied the practical expedients and exemptions and does not disclose the value of remaining performance obligations for (i) contracts with an original expected
length of one year or less; and (ii) contracts for which the variable consideration is allocated entirely to a wholly unsatisfied promise to transfer a distinct service that forms part of a
single performance obligation under the series guidance.

Contract Balances

The following table provides information about the balances of the Company’s trade and client receivables, net of allowance and contract liabilities included in deferred revenue and
other liabilities, noncurrent as of December 31, 2021 and 2020:

(In thousands)
Trade and client receivables, net of allowance
Contract liabilities

Deferred revenue
Deferred revenue (component of other liabilities, noncurrent)

$

2021

2020

66,826  $

22,083 
6,349 

47,018 

16,801 
4,177 

During 2021, changes in the contract liabilities balances were a result of normal business activity and deferral, and subsequent recognition, of revenue related to arrangements with
talent subject to tiered service fees and related allocation of transaction price to material rights.

Revenue recognized during the year ended December 31, 2021 that was included in deferred revenue as of December 31, 2020 was $15.5 million. Revenue recognized during the
year ended December 31, 2020 that was included in deferred revenue as of December 31, 2019 was $13.0 million.

Note 4—Fair Value Measurements and Marketable Securities

The Company defines fair value as the exchange price that would be received from the sale of an asset or paid to transfer a liability in the principal or most advantageous market for
the asset or liability in an orderly transaction between market participants on the measurement date. Valuation techniques used to measure fair value must

87

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

maximize the use of observable inputs and minimize the use of unobservable inputs. The authoritative guidance describes three levels of inputs that may be used to measure fair
value:

•

•

•

Level I—Observable inputs that reflect unadjusted quoted prices for identical assets or liabilities in active markets;

Level  II—Observable  inputs  other  than  Level  I  prices,  such  as  unadjusted  quoted  prices  for  similar  assets  or  liabilities  in  active  markets,  unadjusted  quoted  prices  for
identical or similar assets or liabilities in markets that are not active, or other inputs that are observable or can be corroborated by observable market data for substantially
the full term of the assets or liabilities; and

Level III—Unobservable inputs that are supported by little or no market activity and that are significant to the fair value of the assets or liabilities. These inputs are based on
the Company’s own assumptions used to measure assets and liabilities at fair value and require significant management judgment or estimation.

The categorization of a financial instrument within the fair value hierarchy is based upon the lowest level of input that is significant to its fair value measurement. The Company’s
assessment of the significance of a particular input to the fair value measurement in its entirety requires management to make judgments and consider factors specific to the assets
or liabilities.

The Company’s financial instruments that are carried at fair value consist of Level I and Level II assets as of December 31, 2021 and 2020. The following tables summarize the
Company’s  cash  and  available-for-sale  marketable  securities’  amortized  cost,  gross  unrealized  gains,  gross  unrealized  losses,  and  fair  value  by  significant  investment  category
reported as cash and cash equivalents or marketable securities as of December 31, 2021 and 2020:

(In thousands)

December 31, 2021

Cash
Level I

Money market funds
Treasury bills
U.S. government securities

Total Level I

Level II

Commercial paper
Corporate bonds
Asset-backed securities
Yankee bonds
Total Level II

Total

Amortized
Cost

Unrealized
Gain

Unrealized
Loss

Fair
Value

Cash and
Cash Equivalents

Marketable
Securities

$

16,596  $

—  $

—  $

16,596  $

16,596  $

— 

108,204 
89,992 
94,839 
293,035 

171,918 
183,303 
13,749 
6,693 
375,663 
685,294  $

$

— 
1 
— 
1 

— 
1 
— 
— 
1 
2  $

88

— 
— 
(285)
(285)

— 
(217)
(11)
(12)
(240)
(525) $

108,204 
89,993 
94,554 
292,751 

171,918 
183,087 
13,738 
6,681 
375,424 
684,771  $

108,204 
15,000 
— 
123,204 

29,544 
17,861 
— 
— 
47,405 
187,205  $

— 
74,993 
94,554 
169,547 

142,374 
165,226 
13,738 
6,681 
328,019 
497,566 

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

(In thousands)

December 31, 2020

Cash
Level I

Money market funds
Treasury bills
U.S. government securities

Total Level I

Level II

Commercial paper

Total Level II

Total

Amortized
Cost

Unrealized
Gain

Unrealized
Loss

Fair
Value

Cash and
Cash Equivalents

Marketable
Securities

$

22,359  $

—  $

—  $

22,359  $

22,359  $

— 

65,723 
4,498 
20,082 
90,303 

56,964 
56,964 
169,626  $

$

— 
1 
24 
25 

— 
— 
25  $

— 
— 
— 
— 

— 
— 
—  $

65,723 
4,499 
20,106 
90,328 

56,964 
56,964 
169,651  $

65,723 
— 
— 
65,723 

5,999 
5,999 
94,081  $

— 
4,499 
20,106 
24,605 

50,965 
50,965 
75,570 

The Company did not record any impairment charges with respect to its marketable securities during the years ended December 31, 2021, 2020, and 2019.

As of December 31, 2020, the Company had debt obligations outstanding of $10.8 million under the Company’s Loan and Security Agreement, as amended, which is referred to as
the  Loan  Agreement.  As  of  December  31,  2020,  the  carrying  value  approximated  fair  value  as  borrowings  under  the  Loan  Agreement  bore  interest  at  variable  rates,  and  the
Company believes its credit risk quality is consistent with when the debt was originated. The Company considered the balances outstanding under the Loan Agreement to be Level
II liabilities as of December 31, 2020. As of December 31, 2021, the Loan Agreement had been terminated and no amounts thereunder were outstanding. See “Note 7—Debt.”

Note 5—Balance Sheet Components

Property and Equipment, Net

Property and equipment, net consisted of the following as of December 31, 2021 and 2020:

(In thousands)
Computer equipment and software
Internal-use software and platform development costs
Leasehold improvements
Office furniture and fixtures

Total property and equipment
Less: accumulated depreciation

Property and equipment, net

2021

2020

5,493  $

25,738 
11,644 
3,365 
46,240 
(24,911)
21,329  $

4,819 
20,727 
14,613 
3,354 
43,513 
(15,374)
28,139 

$

$

Depreciation expense related to property and equipment was $3.7 million, $3.6 million, and $2.8 million for the years ended December 31, 2021, 2020, and 2019, respectively.

The Company capitalized $5.0 million, $8.0 million, and $6.4 million of internal-use software and platform development costs during the years ended December 31, 2021, 2020, and
2019, respectively.

Amortization expense related to the capitalized internal-use software and platform development costs was $5.9 million for the year ended December 31, 2021, of which $3.8 million
was included in cost of revenue related to developed technology used on the work marketplace. Amortization expense related to the capitalized internal-use software and platform
development costs was $3.9 million for the year ended December 31, 2020, of which $2.9 million was included in cost of revenue related to developed technology used on the work
marketplace.  Amortization  expense  related  to  the  capitalized  internal-use  software  and  platform  development  costs  was  $1.2  million  for  the  year  ended  December  31,  2019,  of
which $0.9 million was included in cost of revenue related to developed technology used on the work marketplace.

89

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Intangible Assets, Net

All of the Company’s identifiable intangible assets were fully amortized as of December 31, 2021. Total amortization expense of intangible assets was $0.7 million for the year ended
December 31, 2021. Total amortization expense of intangible assets was $2.7 million for each of the years ended December 31, 2020 and 2019. Amortization expense is included in
general and administrative expenses. As of December 31, 2020, intangible assets, net consisted of the following:

(In thousands)
Trade names
User relationships
Developed technology
Domain names

Total

Gross Carrying
Amount

As of December 31, 2020
Accumulated
Amortization

Net Carrying
Amount

$

$

2,293  $

18,678 
10,356 
529 
31,856  $

2,293  $

18,011 
10,356 
529 
31,189  $

Accrued Expenses and Other Current Liabilities

Accrued expenses and other current liabilities consisted of the following as of December 31, 2021 and 2020:

(In thousands)
Accrued compensation and related benefits
Accrued vendor expenses
Operating lease liability, current
Accrued indirect taxes
Accrued payment processing fees
Accrued talent costs
Other

Total accrued expenses and other current liabilities

Operating Leases

2021

2020

$

$

23,047  $
7,728 
6,315 
4,137 
2,085 
1,417 
1,013 
45,742  $

The Company leases office space and certain equipment under various operating leases, with the vast majority of its lease portfolio consisting of operating leases for office space.
The Company has also entered into arrangements where it acts as a sublessor in its leases of office space. The Company has not entered into any significant finance, sales-type, or
direct financing leases.

The Company’s significant judgments include determining whether an arrangement is or contains a lease, the determination of the discount rate used to calculate the lease liability,
and whether or not lease incentives are reasonably certain to occur in the initial measurement of the lease liability. Operating lease assets and lease liabilities are recognized at
commencement date and initially measured based on the present value of lease payments over the defined lease term. Lease expense is recognized on a straight-line basis over
the lease term.

A contract is or contains an embedded lease if the contract meets all of the below criteria:

•

•

•

There is an identified asset;

The Company has the right to obtain substantially all of the economic benefit of the asset; and

The Company has the right to direct the use of the asset.

For initial measurement of the present value of lease payments and for subsequent measurement of lease modifications, the Company is required to use the rate implicit in the
lease. Since the majority of the Company’s leases do not provide an implicit rate, the Company uses its incremental borrowing rate, which is a collateralized rate. The application of
the incremental borrowing rate is performed on a lease-by-lease basis and approximates the rate at which the Company could borrow, on a secured basis for a similar term, an
amount equal to its lease payments in a similar economic environment.

The  Company’s  leases  have  remaining  lease  terms  of  approximately  one  year  to  eight  years,  which  may  include  the  option  to  extend  the  lease.  The  Company  includes  lease
payments associated with renewal options in its operating

90

— 
667 
— 
— 
667 

14,007 
8,662 
3,725 
3,818 
1,219 
1,235 
202 
32,868 

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

lease  asset  and  liability  only  when  it  becomes  reasonably  certain  the  company  will  exercise  the  renewal  option.  The  Company  has  not  included  renewal  options  for  any  of  its
operating leases in its determination of lease liabilities. The Company does not have lease agreements with residual value guarantees, sale leaseback terms, or material restrictive
covenants. Leases with an initial term of 12 months or less are not recognized on the consolidated balance sheet. The Company recognizes lease expense for these leases on a
straight-line basis over the lease term.

The following table summarizes the Company’s operating lease assets and lease liabilities as of December 31, 2021 and 2020:

(In thousands)
Balance Sheet Classification
Assets

Operating—noncurrent

Operating lease asset

Liabilities

Operating—current
Operating—noncurrent

Total lease liabilities

Accrued expenses and other current liabilities
Operating lease liability, noncurrent

2021

2020

$

$

10,682  $

6,315 
16,753 
23,068  $

19,729 

3,725 
20,506 
24,231 

For the years ended December 31, 2021, 2020, and 2019, operating lease cost, inclusive of variable lease charges, was $6.0 million, $6.0 million, and $5.9 million, respectively, and
sublease income recognized was approximately $0.5 million, $0.3 million, and $0.4 million, respectively. For the years ended December 31, 2021, 2020, and 2019, charges related
to operating leases that are variable, and therefore not included in the measurement of the lease liabilities, were $1.2 million, $0.7 million, and $0.6 million, respectively. For the
years ended December 31, 2021, 2020, and 2019, the Company made lease payments of $6.4 million, $3.3 million, and $3.3 million, respectively.

San Francisco Sublease

In  December  2021,  the  Company  executed  a  sublease  agreement  to  sublease  one  of  the  two  suites  the  Company  is  currently  leasing  as  its  headquarters  in  San  Francisco,
California. The suite that was not subleased will continue to be utilized by the Company as it was prior to entering into the sublease agreement. The sublease agreement became
effective in December 2021 upon receipt of the consent of the Company’s landlord. The term of the sublease commences on February 1, 2022 and expires on August 31, 2024,
unless terminated earlier in accordance therewith. Rent payments begin on March 1, 2022 and approximate $0.1 million per month. Rent payments will be recorded within general
and administrative expenses within the Company’s consolidated statements of operations. Neither party has the option to renew or extend the sublease agreement.

Under  the  sublease  agreement,  the  Company  is  not  relieved  of  its  original  obligation  with  the  master  lessor,  which  expires  on  August  31,  2024.  The  Company  determined  the
sublease  agreement  is  an  operating  lease,  which  is  consistent  with  the  classification  of  the  original  sublease  with  the  landlord.  As  a  result  of  the  execution  of  the  sublease
agreement,  the  Company  determined  that  indicators  of  impairment  existed  with  respect  to  the  asset  group  that  consisted  of  the  operating  lease  asset  and  related  leasehold
improvements associated with the suite being subleased. Accordingly, the Company conducted an impairment test to assess whether the fair value of the asset group was lower
than its carrying value. The results of the impairment test indicated that the fair value of the asset group was lower than its carrying value. The Company determined the fair value of
the asset group using the discounted cash flow method. The assumptions used in the discounted cash flow analysis included projected sublease income over the remaining term of
the  original  lease  with  the  landlord  and  a  discount  rate  the  Company  believes  reflects  the  level  of  risk  associated  with  these  future  cash  flows.  The  Company  considers  these
assumptions to be Level III inputs in accordance with the fair value hierarchy described in “Note 4—Fair Value Measurements and Marketable Securities.”

As a result of the partial sublease of its San Francisco office, during the year ended December 31, 2021, the Company recorded an impairment charge of $1.4 million, of which
$1.2 million was allocated to the operating lease asset and $0.2 million was allocated to the associated leasehold improvements. The Company recorded this impairment charge
within general and administrative expenses within its consolidated statement of operations for the year ended December 31, 2021.

91

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Santa Clara Sub-Sublease

In April 2021, the Company executed a sub-sublease agreement to sublease the entirety of its former headquarters in Santa Clara, California. The sub-sublease agreement became
effective in May 2021 upon receipt of the consent of the Company’s landlord and master lessor. The term of the sub-sublease commenced on June 1, 2021 and expires on May 31,
2024, unless terminated earlier in accordance therewith. Rent payments begin on January 1, 2022 and approximate $0.1 million per month. Rent payments will be recorded within
general and administrative expenses within the Company’s consolidated statements of operations. Neither party has the option to renew or extend the sub-sublease agreement.

Under the sub-sublease agreement, the Company is not relieved of its original obligation with the master lessor that expires on October 15, 2028. The Company determined the
sub-sublease agreement is an operating lease, which is consistent with the classification of the original sublease with the master lessor. As a result of the execution of the sub-
sublease agreement, the Company determined that indicators of impairment existed with respect to the asset group that consisted of the Santa Clara office operating lease asset
and associated leasehold improvements, furniture and fixtures, and hardware. Accordingly, the Company conducted an impairment test to assess whether the fair value of the asset
group  was  lower  than  its  carrying  value.  The  results  of  the  impairment  test  indicated  that  the  fair  value  of  the  asset  group  was  lower  than  its  carrying  value.  The  Company
determined  the  fair  value  of  the  asset  group  using  the  discounted  cash  flow  method.  The  assumptions  used  in  the  discounted  cash  flow  analysis  included  projected  sublease
income  over  the  remaining  term  of  the  original  sublease  with  the  master  lessor,  expected  downtime  prior  to  the  commencement  of  future  subleases,  and  a  discount  rate  the
Company believes reflects the level of risk associated with these future cash flows. The Company considers these assumptions to be Level III inputs in accordance with the fair
value hierarchy described in “Note 4—Fair Value Measurements and Marketable Securities.”

As a result of the sublease of its Santa Clara office, during the year ended December 31, 2021, the Company recorded an impairment charge of $7.4 million, of which $4.3 million
was allocated to the Santa Clara office operating lease asset, $2.9 million was allocated to the associated leasehold improvements, and $0.2 million was allocated to the associated
furniture and fixtures and hardware. The Company recorded this impairment charge within general and administrative expenses within its consolidated statement of operations for
the year ended December 31, 2021.

Chicago Lease

On January 1, 2020, the Company commenced an operating lease of one additional floor in its Chicago, Illinois office. As a result, the Company recognized a $1.7 million operating
lease asset and $1.7 million operating lease liability on January 1, 2020, which are included in operating lease asset and operating lease liability, noncurrent, respectively, on the
Company’s consolidated balance sheet as of December 31, 2020. The lease has an initial term of five years with the option to renew for an additional five years at the end of the
initial lease term. Total minimum lease payments under the initial term are $2.1 million. For the initial measurement of the present value of the lease payments associated with this
lease, the Company used its incremental borrowing rate, which is a collateralized rate and approximates the rate at which the Company could borrow, on a secured basis for a
similar term, an amount equal to its lease payments in a similar economic environment.

As of December 31, 2021 and 2020, the Company had no material finance leases.

92

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

The following table shows the Company’s future lease commitments due in each of the next five years and thereafter for operating leases, which excludes amounts received in the
form of sublease income discussed above:

(In thousands)
Year Ended December 31,
2022
2023
2024
2025
2026
Thereafter

Total lease payments

Adjustment for discount to present value

Total

Leases

6,588 
6,776 
5,843 
2,356 
1,729 
3,208 
26,500 
(3,432)
23,068 

$

$

As of and for the year ended December 31, 2021, the weighted-average remaining lease term is 4.6 years, and the weighted-average discount rate is 5.80%.

Note 6—Commitments and Contingencies

Letters of Credit

In  conjunction  with  the  Company’s  operating  lease  agreements,  as  of  December  31,  2021  and  2020,  the  Company  had  three  irrevocable  letters  of  credit  outstanding  in  the
aggregate amounts of $0.8 million and $1.0 million, respectively. The letters of credit are collateralized by restricted cash in the same amount. No amounts had been drawn against
these letters of credit as of December 31, 2021 and 2020.

Contingencies

The Company accrues contingent liabilities when it is probable that future expenditures will be made and such expenditures can be reasonably estimated. Potential contingencies
may  include  various  claims  and  litigation  or  non-income  tax  matters  that  arise  from  time  to  time  in  the  normal  course  of  business.  Due  to  uncertainties  inherent  in  such
contingencies, the Company can give no assurance that it will prevail in any such matters, which could subject the Company to significant liability or damages. Any claims, litigation,
or other contingencies could have an adverse effect on the Company’s business, financial position, results of operations or cash flows in or following the period that claims, litigation
or other contingencies are resolved.

As of December 31, 2021 and 2020, the Company was not a party to any material legal proceedings or claims, nor is the Company aware of any pending or threatened litigation or
claims, including non-income tax matters, that could reasonably be expected to have a material adverse effect on its business, operating results, cash flows, or financial condition.
Accordingly, the amounts accrued for contingencies for which the Company believes a loss is probable were not material as of and for the years ended December 31, 2021 and
2020.

Indemnification

The  Company  has  indemnification  agreements  with  its  officers,  directors,  and  certain  key  employees  to  indemnify  them  while  they  are  serving  in  good  faith  in  their  respective
positions. In the ordinary course of business, the Company enters into contractual arrangements under which it agrees to provide indemnification of varying scope and terms to
clients, business partners, vendors, and other parties, including, but not limited to, losses arising out of the Company’s breach of such agreements, claims related to potential data
or information security breaches, intellectual property infringement claims made by third parties, and other liabilities relating to or arising from the Company’s offerings and services
or  its  acts  or  omissions.  In  addition,  subject  to  the  terms  of  the  applicable  agreement,  as  part  of  the  Company’s  Upwork  Enterprise  and  certain  other  premium  offerings,  the
Company indemnifies clients that subscribe to worker classification services for losses arising from worker misclassification. It is not possible to determine the maximum potential
loss  under  these  indemnification  provisions  due  to  the  Company’s  limited  history  of  prior  indemnification  claims  and  the  facts  and  circumstances  involved  in  each  particular
provision.

93

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Note 7—Debt

The following table presents the carrying value of the Company’s debt obligations as of December 31, 2021 and 2020:

(In thousands)
Convertible  senior  notes—interest  accrues  from  August  2021  and  will  be  payable  semiannually  in  arrears  on  February  15  and
August 15 of each year, beginning February 2022, maturing August 2026; interest at 0.25% per annum

$

2021

2020

575,000 

$

— 

First term loan—18 months of interest-only payments ended in March 2019 followed by 36 equal monthly installments of principal
plus interest, maturing March 2022; interest at prime plus 0.25% per annum
Second  term  loan—17  months  of  interest-only  payments  ended  in  March  2019  followed  by  42  equal  monthly  installments  of
principal plus interest, maturing September 2022; interest at prime plus 0.25% per annum

Total debt

Less: Unamortized debt issuance costs

Balance

Debt, current

Debt, noncurrent

Weighted-average interest rate

Term and Revolving Loans

— 

— 

575,000 

(13,701)

561,299 

— 

$

561,299 

$

6,250 

4,500 

10,750 

(27)

10,723 

(7,581)

3,142 

0.76 %

5.64 %

The  Loan  Agreement,  which  was  subsequently  amended  in  November  2017,  September  2018,  March  2019,  and  August  2020,  was  terminated  in  August  2021.  Under  the  Loan
Agreement, the aggregate amount of the facility was up to $49.0 million, consisting of a term loan in the original principal amount of $15.0 million, which is referred to as the First
Term Loan, a term loan in the original principal amount of $9.0 million, which is referred to as the Second Term Loan and, together with the First Term Loan, as the Term Loans, and
a revolving line of credit, which permitted borrowings of up to $25.0 million subject to customary conditions.

In August 2021, the Company entered into an agreement, which is referred to as the Payoff Agreement, with its lender to fully repay the remaining outstanding principal amounts
plus accrued and unpaid interest outstanding under its Term Loans and terminate the Loan Agreement. There were no amounts outstanding under the Company’s revolving line of
credit  as  of  the  date  of  termination.  Pursuant  to  the  Payoff  Agreement,  the  full  repayment  of  the  Term  Loans  amounted  to  $5.8  million,  and  as  of  August  5,  2021,  the  Loan
Agreement, including the Term Loans and revolving line of credit, was terminated. As of December 31, 2021, no amounts remained outstanding under the Loan Agreement. The
Company was in compliance with its covenants under the Loan Agreement as of August 5, 2021 and December 31, 2020.

During the year ended December 31, 2021, the Company repaid $6.3 million and $4.5 million related to the First Term Loan and the Second Term Loan, respectively. During the
year ended December 31, 2020, the Company repaid $5.0 million and $2.6 million related to the First Term Loan and the Second Term Loan, respectively. Amortization expense
related to the debt discount was immaterial for the years ended December 31, 2021, 2020, and 2019.

Convertible Senior Notes Due 2026

On  August  10,  2021,  the  Company  issued,  at  par  value,  $575.0  million  aggregate  principal  amount  of  0.25%  convertible  senior  notes  due  2026.  The  issuance  included  the  full
exercise of an option granted by the Company to the initial purchasers of the Notes to purchase an additional $75.0 million aggregate principal amount of Notes. The Notes were
issued  pursuant  to  and  are  subject  to  the  terms  and  conditions  of  an  indenture,  which  is  referred  to  as  the  Indenture,  between  the  Company  and  Wells  Fargo  Bank,  National
Association, as trustee. The Notes were offered and sold in a private offering to qualified institutional buyers pursuant to Rule 144A under the Securities Act of 1933, as amended.

The  Notes  are  senior,  unsecured  obligations  of  the  Company  and  will  bear  interest  at  a  rate  of  0.25%  per  year.  Interest  will  accrue  from  August  10,  2021  and  will  be  payable
semiannually in arrears on February 15 and August 15 of each year, beginning on February 15, 2022, and the principal amount of the Notes will not accrete. The Notes will mature
on August 15, 2026, unless earlier redeemed, repurchased, or converted in accordance with the terms of the Notes.

94

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Holders  may  convert  all  or  any  portion  of  their  Notes,  in  multiples  of  $1,000  principal  amount  at  the  option  of  the  holder  (i)  prior  to  the  close  of  business  on  the  business  day
immediately preceding May 15, 2026, only upon satisfaction of certain conditions and during certain periods specified below, and (ii) on or after May 15, 2026, at any time until the
close of business on the second scheduled trading day immediately preceding the maturity date:

•

•

•

•

during any calendar quarter commencing after the calendar quarter ending on December 31, 2021, if the last reported sale price of the Company’s common stock is greater
than  or  equal  to  130%  of  the  conversion  price  for  at  least  20  trading  days  (whether  or  not  consecutive)  during  a  period  of  30  consecutive  trading  days  ending  on,  and
including, the last trading day of the immediately preceding calendar quarter of the conversion price on each applicable trading day;

during the five consecutive business day period after any five consecutive trading day period, which is referred to as the Measurement Period, in which the trading price (as
defined in the Indenture) per $1,000 principal amount of Notes for each trading day of the Measurement Period was less than 98% of the product of the last reported sale
price per share of the Company’s common stock on such trading day and the conversion rate on such trading day;

if the Company calls such Notes for redemption, at any time prior to the close of business on the second scheduled trading day immediately preceding the redemption date;
and

upon the occurrence of specified corporate events described in the Indenture.

Upon  conversion,  the  Notes  may  be  settled  in  shares  of  the  Company’s  common  stock,  cash  or  a  combination  of  cash  and  shares  of  the  common  stock,  at  the  election  of  the
Company.  The  Notes  have  an  initial  conversion  rate  of  15.1338  shares  of  common  stock  per  $1,000  principal  amount  of  Notes,  which  is  subject  to  adjustment  in  certain
circumstances. This is equivalent to an initial conversion price of approximately $66.08 per share of the Company’s common stock. The conversion rate is subject to customary
adjustments under certain circumstances in accordance with the terms of the Indenture. In addition, if certain corporate events that constitute a make-whole fundamental change (as
defined  in  the  Indenture)  occur  or  if  the  Company  issues  a  notice  of  redemption  with  respect  to  the  Notes  prior  to  the  maturity  date,  then  the  conversion  rate  will,  in  certain
circumstances, be increased for a specified period of time.

The  Company  may  redeem  for  cash  all  or  any  portion  of  the  Notes  (subject  to  a  partial  redemption  limitation),  at  the  Company’s  option,  on  or  after  August  20,  2024,  if  the  last
reported sale price per share of the Company’s common stock has been at least 130% of the conversion price then in effect for at least 20 trading days (whether or not consecutive)
during any 30 consecutive trading day period (including the last trading day of such period) ending on, and including, the trading day immediately preceding the date on which the
Company provides notice of redemption at a redemption price equal to 100% of the principal amount of the Notes to be redeemed, plus any accrued and unpaid interest, if any, to,
but excluding, the redemption date. No sinking fund is provided for the Notes, which means that the Company is not required to redeem or retire the Notes periodically.

Upon the occurrence of a fundamental change (as defined in the Indenture), subject to certain conditions, holders have the right to require the Company to repurchase for cash all
or a portion of their Notes at a price equal to 100% of the principal amount of the Notes to be repurchased, plus any accrued and unpaid interest thereon, if any, until, but excluding,
the fundamental change repurchase date.

The  Notes  are  the  Company’s  senior  unsecured  obligations  and  rank  senior  in  right  of  payment  to  any  of  the  Company’s  existing  and  future  indebtedness  that  is  expressly
subordinated in right of payment to the Notes; equal in right of payment to any of the Company’s existing and future unsecured indebtedness that is not so subordinated; effectively
junior in right of payment to any of the Company’s existing and future secured indebtedness to the extent of the value of the assets securing such indebtedness; and structurally
junior to all existing and future indebtedness and other liabilities (including trade payables) of the Company’s subsidiaries.

The net proceeds from the issuance of the Notes were approximately $560.1 million, after deducting debt issuance costs. The total debt issuance costs incurred and recorded by
the Company amounted to $14.9 million, which were recorded as a reduction to the face amount of the Notes and will be amortized to interest expense on a straight-line basis,
which produces a materially consistent amount as the effective interest method over the contractual term of the Notes.

For the year ended December 31, 2021, interest expense was $0.6 million and amortization of the issuance costs was $1.1 million related to the Notes. As of December 31, 2021,
the if-converted value of the Notes did not exceed the outstanding principal amount. As of December 31, 2021, the total estimated fair value of the Notes was $538.3 million and
was determined based on a market approach using actual bids and offers of the Notes in an

95

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

over-the-counter market on the last trading day of the period. The Company considers these assumptions to be Level II inputs in accordance with the fair value hierarchy described
in “Note 4—Fair Value Measurements and Marketable Securities.”

Capped Calls

In  connection  with  the  pricing  of  the  Notes  on  August  5,  2021  and  in  connection  with  the  full  exercise  by  the  initial  purchasers  on  August  9,  2021  of  their  option  to  purchase
additional  Notes,  the  Company  used  approximately  $49.4  million  of  the  net  proceeds  from  the  issuance  of  the  Notes  to  enter  into  privately  negotiated  capped  call  transactions,
which are referred to as the Capped Calls, with various financial institutions.

Subject to customary anti-dilution adjustments substantially similar to those applicable to the Notes, the Capped Calls cover the number of shares of the Company’s common stock
initially underlying the Notes. By entering into the Capped Calls, the Company expects to reduce the potential dilution to its common stock (or, in the event a conversion of the Notes
is settled in cash, to reduce its cash payment obligation) in the event that at the time of conversion of the Notes its common stock price per share exceeds the conversion price of
the Notes, with such reduction subject to a cap based on the cap price. If, however, the market price per share of common stock, as measured under the terms of the Capped Calls,
exceeds the cap price of the Capped Calls, there would be dilution and/or there would not be an offset of such potential cash payments, in each case, to the extent that the then-
market  price  per  share  of  common  stock  exceeds  the  cap  price  of  the  Capped  Calls.  The  initial  cap  price  of  the  Capped  Calls  is  $92.74  per  share  of  common  stock,  which
represents a premium of 100% over the last reported sale price of the common stock of $46.37 per share on August 5, 2021, and is subject to certain customary adjustments under
the terms of the Capped Calls; provided that the cap price will not be reduced to an amount less than the strike price of $66.08 per share.

The  Capped  Calls  are  separate  transactions  and  are  not  part  of  the  terms  of  the  Notes.  The  Capped  Calls  meet  the  criteria  for  classification  as  equity  and,  as  such,  are  not
remeasured each reporting period and are included as a reduction to additional paid-in-capital within stockholders’ equity.

Note 8—Preferred and Common Stock

Preferred Stock

As of December 31, 2021 and 2020, the Company was authorized to issue up to 10,000,000 shares of undesignated preferred stock, $0.0001 par value per share. The Company
did not have any outstanding shares of preferred stock as of December 31, 2021 and 2020.

Common Stock

Holders of common stock are entitled to one vote per share and are entitled to receive dividends, if any, on a pro rata basis whenever funds are legally available and when, as, and
if declared by the Company’s board of directors.

96

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

As of December 31, 2021 and 2020, the Company was authorized to issue 490,000,000 shares of common stock. As of December 31, 2021 and 2020, the Company had reserved
shares of common stock for future issuance as follows:

Options issued and outstanding
RSUs and PSUs issued and outstanding
Warrant to purchase common stock
Remaining shares reserved for future issuances under 2018 Equity Incentive Plan
Remaining shares reserved for future issuances under 2018 Employee Stock Purchase Plan
Common stock issuable in connection with convertible senior notes

Total

Common Stock Warrant

2021

2020

4,264,068 
4,583,823 
350,000 
22,250,297 
3,033,401 
8,701,935 
43,183,524 

4,858,590 
5,568,225 
400,000 
18,332,765 
2,419,154 
— 
31,578,734 

In  2018,  the  Company  established  The  Upwork  Foundation  initiative.  The  program  includes  a  donor-advised  fund  created  through  the  Tides  Foundation.  In  2018,  the  Company
issued a warrant to purchase 500,000 shares of its common stock at an exercise price of $0.01 per share to the Tides Foundation. The vesting and exercisability provisions of the
warrant became effective upon the Company’s initial public offering, which is referred to as the IPO, in October 2018. This warrant is exercisable as to 1/10th of the shares on each
anniversary of the IPO, with proceeds from the sale of such shares to be donated in accordance with the Company’s directive.

In  each  of  2019,  2020,  and  2021  this  warrant  was  exercised  as  to  all  50,000  of  the  then-vested  and  exercisable  shares.  In  lieu  of  a  cash  payment,  the  holder  of  the  warrant
surrendered shares of common stock to cover the exercise price. For the years ended December 31, 2021, 2020, and 2019, the Company recorded $0.8 million, $0.8 million, and
$0.7 million, respectively, of expense related to this warrant, which is included in general and administrative expense in the Company’s consolidated statement of operations.

Note 9—Stock-Based Compensation

Equity Incentive Plans

2014 Equity Incentive Plan

In  2014,  the  Company’s  board  of  directors  and  stockholders  each  adopted  the  2014  Equity  Incentive  Plan,  which  is  referred  to  as  the  2014  EIP.  The  total  number  of  shares  of
common stock reserved and available for grant and issuance pursuant to such plan was originally 12,462,985 plus (i) shares that were then subject to outstanding option grants
under the oDesk Corporation 2004 Stock Plan, the Elance 1999 Stock Option Plan, and the Elance 2009 Stock Option Plan, which are referred to collectively as the Prior Plans, but
subsequently ceased to be subject to an award for any reason other than exercise of a stock option, (ii) shares that had been reserved but not subject to any outstanding awards
under the Prior Plans and (iii) shares issued under the Prior Plans that were repurchased, forfeited, or used to pay employee withholding or exercise price obligations. Under the
terms of the 2014 EIP, incentive stock options may be granted at prices not less than 100% of the fair value of the Company’s common stock on the date of grant unless determined
in writing by the Company’s board of directors. The options granted under the 2014 EIP generally vest over a four-year period from the original date of grant and expire ten years
from the original grant date.

2018 Equity Incentive Plan

In 2018, the Company’s board of directors and stockholders each adopted the 2018 Equity Incentive Plan, which is referred to as the 2018 EIP, which became effective on the date
immediately  prior  to  the  date  of  the  IPO.  A  total  of  10,701,505  shares  of  common  stock  were  initially  reserved  for  issuance  pursuant  to  future  awards  under  the  2018  EIP.  On
January 1 of each year, shares available for issuance are increased based on the provisions of the 2018 EIP. Any shares subject to outstanding awards under the 2014 EIP that are
canceled or repurchased subsequent to the 2018 EIP’s effective date are returned to the pool of shares reserved for issuance under the 2018 EIP. Awards granted under the 2018
EIP may be (i) incentive stock options, (ii) nonqualified stock options, (iii) RSUs, (iv) restricted stock awards, or (v) stock appreciation rights, as determined by the Company’s board
of directors or compensation committee at the time of grant.

97

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Pursuant to the terms of the 2018 EIP, the number of shares available for grant was increased by 6,239,761 shares in January 2021.

Option Awards

The  fair  value  of  options  with  service-  and  performance-based  conditions  is  determined  using  the  Black-Scholes  valuation  model  as  of  the  grant  date  using  the  following
assumptions:

Dividend Yield—The dividend yield is assumed to be zero as the Company has never paid dividends and has no current plans to do so.

Expected Term—The expected term represents the period that the Company’s stock-based awards are expected to be outstanding. For awards containing only service conditions,
the Company determines the expected term using the simplified method as the Company did not have sufficient historical information to develop reasonable expectations about
future exercise patterns and post-vesting employment termination behavior at the time of grant. The simplified method deems the term to be the average of the time-to-vesting and
the contractual life of the options. For performance-based awards, the Company uses relevant data, including past exercise patterns, if available, to determine the expected term.

Risk-Free  Interest  Rate—The  risk-free  interest  rate  is  based  on  the  United  States  Treasury  yield  curve  in  effect  at  the  time  of  grant  for  zero-coupon  U.S.  Treasury  notes  with
maturities approximately equal to the option’s expected term.

Expected Volatility—Since the Company did not have a sufficient trading history of its common stock at the time of grant, the expected volatility is derived from the average historical
stock volatilities of several unrelated public companies within the Company’s industry that the Company considers to be comparable to its business over a period equivalent to the
expected term of the stock option grants.

Fair  Value  of  Common  Stock—Given  the  absence  of  a  public  trading  market  prior  to  the  IPO,  the  Company’s  board  of  directors  considered  numerous  objective  and  subjective
factors to determine the fair value of its common stock at each grant date. These factors included, but were not limited to: (i) independent contemporaneous third-party valuations of
common stock; (ii) the prices for the Company’s redeemable convertible preferred stock sold to outside investors; (iii) the rights and preferences of redeemable convertible preferred
stock relative to common stock; (iv) the lack of marketability of its common stock; (v) developments in the business; and (vi) the likelihood of achieving a liquidity event, such as an
initial  public  offering  or  sale  of  the  Company,  given  prevailing  market  conditions.  Subsequent  to  the  IPO,  the  fair  value  of  common  stock  is  based  on  the  closing  price  of  the
Company’s common stock, as reported on The Nasdaq Global Select Market on the date of grant.

The following table summarizes activity under the Company’s stock option plans:

Balances at December 31, 2020

Granted
Exercised
Forfeited and canceled

Balances at December 31, 2021
Vested and exercisable as of December 31, 2021
Vested and expected to vest as of December 31, 2021

Number of Shares
Underlying
Outstanding Options

Weighted-
Average
Exercise Price

Weighted-Average
Remaining Contractual
Term (Years)

Aggregate
Intrinsic Value
(in thousands)

4,858,590  $
1,500,000 
(2,035,709)
(58,813)
4,264,068 

2,542,329 
4,264,068 

3.83 
38.80 
3.53 
4.42 

16.29 
4.02 
16.29 

5.80 $

149,046 

6.37
4.80
6.37

76,025 
76,626 
76,025 

98

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

In 2021, the compensation committee of the Company’s board of directors approved a stock option grant, which is referred to as the CEO Award, exercisable for up to 1,500,000
shares of the Company’s common stock to Hayden Brown, the Company’s President and Chief Executive Officer, under the 2018 EIP. The CEO Award is subject to a service-based
vesting requirement, which is referred to as the Service Condition, and a performance-based vesting requirement, which is referred to as the Market Condition. In order for any
shares subject to the CEO Award to be exercisable, both the Service Condition and the Market Condition must be satisfied with respect to such shares. The CEO Award vests with
respect  to  the  Service  Condition  in  sixteen  equal  quarterly  installments  following  the  grant  date,  subject  to  Ms.  Brown’s  continuous  service  to  the  Company  as  Chief  Executive
Officer,  Executive  Chairperson,  or  any  C-level  officer  position.  The  CEO  Award  vests  with  respect  to  the  Market  Condition  upon  the  achievement  of  certain  volume  weighted-
average  common  stock  price  targets  measured  over  any  consecutive  90-day  period  between  the  grant  date  and  April  18,  2026.  The  90-day  volume  weighted-average  common
stock price targets, and the number of shares of the CEO Award that become vested with respect to the Market Condition upon the achievement of each such target, are reflected in
the following table:

Stock Price
$60
$70
$80
$90
$100

Number of Shares Vested
100,000
200,000
300,000
400,000
500,000

Stock-based  compensation  expense  associated  with  the  CEO  Award  will  be  recognized  over  the  longer  of  the  expected  achievement  period  for  the  Market  Condition  and  the
Service  Condition.  The  Market  Condition  period  and  the  valuation  of  each  tranche  of  the  CEO  Award  were  determined  using  a  Monte  Carlo  simulation.  In  the  event  the  Market
Condition  is  met  prior  to  the  expected  achievement  period,  any  then-unrecognized  compensation  expense  associated  with  the  shares  that  have  vested  with  respect  to  both  the
Market Condition and the Service Condition will be recognized immediately in the Company’s consolidated statements of operations. For the year ended December 31, 2021, the
Company  recorded  stock-based  compensation  expense  of  $11.3  million  related  to  the  CEO  Award.  Stock-based  compensation  expense  for  the  CEO  Award  is  recorded  as  a
component of general and administrative expense in the Company’s consolidated statement of operations.

The Company estimated the fair value of the CEO Award using a Monte Carlo simulation. The Company estimates the expected term based on a future exercise assumption. The
weighted-average derived service period for the CEO Award is 2.1 years. The risk-free interest rate is based on the United States Treasury yield curve in effect at the time of grant
for zero-coupon U.S. Treasury notes. The expected volatility is derived from the average historical stock volatility of the Company over a period equivalent to the expected term of
the CEO Award. The following assumptions were used to estimate the fair value of the CEO Award:

Dividend yield

Risk-free interest rates

Expected volatility

— %

1.7 %

65 %

In  2019,  the  Company  entered  into  a  transition  agreement,  which  is  referred  to  as  the  Transition  Agreement,  with  Stephane  Kasriel  pursuant  to  which  Mr.  Kasriel  tendered  his
resignation as the Company’s President and Chief Executive Officer effective as of December 31, 2019. As a result, for the year ended December 31, 2019, the Company recorded
$3.5 million of additional stock-based compensation expense related to the Transition Agreement.

The fair values of the awards modified by the Transition Agreement were estimated using the Black-Scholes valuation model with the following assumptions:

Dividend yield

Expected term (in years)

Risk-free interest rates

Expected volatility

— %

0.3 - 1.3

1.5% - 1.6%

38% - 39%

For the years ended December 31, 2021, 2020, and 2019, the intrinsic value of options exercised was $88.9 million, $124.1 million, and $73.0 million, respectively. The aggregate
intrinsic value represents the difference between the

99

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

exercise price of the options and the closing price of the Company’s common stock on The Nasdaq Global Select Market on the day prior to the date of exercise.

For the year ended December 31, 2021, the weighted-average grant-date fair value of options granted was $19.19. The Company did not grant any stock option awards during the
years  ended  December  31,  2020  and  2019.  As  of  December  31,  2021,  total  unrecognized  stock-based  compensation  cost  was  $17.9  million,  which  is  expected  to  be  generally
recognized on a straight-line basis over a weighted-average period of 1.8 years.

RSU and PSU Awards

The fair value of RSUs awarded to employees is based on the closing price of the Company’s common stock, as reported on The Nasdaq Global Select Market on the date of grant.

The following table summarizes the RSU and PSU activity and related information under the 2018 EIP:

Unvested balance - January 1, 2021
Granted
Vested
Forfeited/canceled

Unvested balance - December 31, 2021

Number
Outstanding

Weighted-Average
Grant Date Fair Value

5,568,225  $
2,075,311 
(1,865,444)
(1,194,269)
4,583,823  $

12.20 
51.53 
16.37 
16.42 
26.86 

In 2021, the compensation committee of the Company’s board of directors approved PSU grants to certain members of the Company’s leadership team under the 2018 EIP. The
number of PSUs that were earned by the recipients, which are referred to as Earned PSUs, was determined based on the Company’s revenue achievement during the year ended
December 31, 2021, which is referred to as the PSU Performance Condition. The Earned PSUs are subject to a time-based vesting requirement conditioned on the recipient of the
PSU Award continuing to provide service to the Company for four years from the PSU Grant Date, which is referred to as the PSU Service Condition. The Earned PSUs will vest
with respect to 25% of the Earned PSUs on the one-year anniversary of the PSU Grant Date and 1/16th of the Earned PSUs on a quarterly basis thereafter.

Stock-based compensation expense associated with the PSU Awards is a component of operating expenses in the Company’s consolidated statements of operations and will be
recognized over the longer of the expected achievement period for the PSU Performance Condition and the PSU Service Condition. The grant date fair value of the PSU Awards
was determined using the Company’s closing common stock price on the PSU Grant Date multiplied by the number of PSUs that were probable of being earned on the PSU Grant
Date.  At  each  interim  reporting  date  prior  to  the  date  on  which  the  compensation  committee  of  the  Company’s  board  of  directors  certifies  the  PSU  Performance  Condition,  the
number of PSUs that are probable of being earned is reassessed and any changes are reflected in the total stock-based compensation expense associated with the PSU Awards.

For  the  year  ended  December  31,  2021,  the  weighted-average  grant-date  fair  value  of  PSUs  granted  was  $56.42.  During  the  year  ended  December  31,  2021,  the  Company
recorded stock-based compensation expense of $3.4 million related to the PSUs. As of December 31, 2021, unrecognized stock-based compensation cost was $3.4 million, which
is expected to be recognized over a weighted-average period of 1.8 years.

For the years ended December 31, 2021, 2020, and 2019, the weighted-average grant-date fair value of RSUs granted was $51.37, $10.96, and $16.15, respectively. For the years
ended December 31, 2021, 2020, and 2019, the fair value of RSUs vested was $30.5 million, $20.3 million, and $2.6 million, respectively. As of December 31, 2021, there was
$108.1 million of unrecognized stock-based compensation expense related to outstanding RSUs to employees that is expected to be recognized over a weighted-average period of
3.1 years.

2018 Employee Stock Purchase Plan

In 2018, the Company’s board of directors and stockholders each adopted the 2018 ESPP. A total of 1,700,000 shares of common stock was initially reserved for issuance under
the 2018 ESPP. On January 1 of each year, shares available for issuance are increased based on the provisions of the 2018 ESPP. The 2018 ESPP allows eligible employees to
purchase shares of the Company’s common stock at a discount of up to 15% through payroll deductions of their eligible compensation, subject to any plan limitations. Except for the
initial offering period, the 2018 ESPP provides for 24-month offering periods beginning November 15 and May 15 of each year, and each

100

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

offering period consists of four 6-month purchase periods. Pursuant to the terms of the 2018 ESPP, in January 2021, the number of shares of common stock available for issuance
was increased by 998,361 shares.

For the years ended December 31, 2021, 2020, and 2019, the assumptions used to determine the fair value of the shares to be awarded was estimated on the grant date using the
Black-Scholes valuation model with the following assumptions:

Dividend yield

Expected term (in years)

Risk-free interest rates

Expected volatility

2021

2020

2019

— %

0.5 - 2.0

—% - 0.5%

60% - 76%

— %

0.5 - 2.0

0.1% - 0.2%

50% - 82%

— %

0.5 - 2.0

1.5% - 2.4%
38%

On  each  purchase  date,  eligible  employees  may  purchase  the  Company’s  common  stock  at  a  price  per  share  equal  to  85%  of  the  lesser  of  (1)  the  fair  market  value  of  the
Company’s common stock on the offering date or (2) the fair market value of the Company’s common stock on the purchase date. In the event the price is lower on the last day of
any purchase period, that price is used as the purchase price for that purchase period.

Additionally, in the event the fair market value of the Company’s common stock on the first day of a subsequent offering period is less than the fair market value of the Company’s
common stock on the offering date of the current offering period, the offering period resets, and the new lower price becomes the new offering price for a new 24 month offering
period. During the year ended December 31, 2021, the Company issued 384,114 shares of common stock under the 2018 ESPP.

As of December 31, 2021, there was $5.8 million of unrecognized stock-based compensation expense that is expected to be recognized over the remaining term of the respective
offering periods.

Stock-Based Compensation

The following table summarizes the components of stock-based compensation expense recognized in the consolidated statements of operations for the years ended December 31,
2021, 2020, and 2019:

(In thousands)
Cost of revenue
Research and development
Sales and marketing
General and administrative

Total

Stock-Based Compensation to Employees

2021

2020

2019

$

$

794  $

16,232 
5,923 
30,643 
53,592  $

779  $

9,783 
4,440 
10,506 
25,508  $

456 
6,471 
2,609 
9,262 
18,798 

Stock-based compensation expense related to employees for the year ended December 31, 2021 was $12.7 million, $38.8 million, and $2.2 million related to stock option grants,
RSU  and  PSU  grants,  and  the  2018  ESPP,  respectively.  Stock-based  compensation  expense  related  to  employees  for  the  year  ended  December  31,  2020  was  $2.5  million,
$20.0 million, and $3.2 million related to stock option grants, RSU grants, and the 2018 ESPP, respectively. Stock-based compensation expense related to employees for the year
ended December 31, 2019 was $8.5 million, $7.9 million, and $2.6 million related to stock option grants, RSUs, and the 2018 ESPP, respectively.

101

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Note 10—Net Loss per Share

The following table sets forth the computation of the Company’s basic and diluted net loss per share for the years ended December 31, 2021, 2020, and 2019:

 (In thousands, except share and per share data)
Numerator:
Net loss
Denominator:

Weighted-average shares used to compute net loss per share, basic and diluted

Net loss per share, basic and diluted

2021

2020

2019

$

$

(56,240) $

(22,867) $

(16,659)

127,163,591 

118,698,567 

(0.44) $

(0.19) $

109,814,604 
(0.15)

For  the  years  ended  December  31,  2021,  2020,  and  2019,  the  following  potentially  dilutive  shares  were  excluded  from  the  computation  of  diluted  net  loss  per  share  because
including them would have been anti-dilutive:

Options to purchase common stock
Common stock issuable upon exercise of common stock warrants
Common stock issuable upon vesting of RSUs and PSUs
Common stock issuable in connection with employee stock purchase plan
Common stock issuable in connection with convertible senior notes

Total

Note 11—Income Taxes

2021

2020

2019

4,264,068 
350,000 
4,583,823 
329,650 
8,701,935 
18,229,476 

4,858,590 
400,000 
5,568,225 
540,580 
— 
11,367,395 

15,140,579 
450,000 
2,503,182 
1,651,263 
— 
19,745,024 

For the years ended December 31, 2021, 2020, and 2019, the loss before income taxes consisted of the following:

(In thousands)
Domestic
Foreign

Total loss before income taxes

2021

2020

2019

$

$

(56,165) $
47 
(56,118) $

(22,748) $
31 
(22,717) $

(16,658)
27 
(16,631)

For the years ended December 31, 2021, 2020, and 2019, the components of the income tax provision were as follows:

(In thousands)
Current:

Federal
State
Foreign

Total current

Deferred:
Federal
State
Foreign

Total deferred

Total income tax benefit (provision)

2021

2020

2019

$

$

$

$
$

—  $

(120)
(2)
(122) $

—  $
— 
— 
—  $
(122) $

(19) $

(127)
(4)
(150) $

—  $
— 
— 
—  $
(150) $

— 
(26)
(2)
(28)

— 
— 
— 
— 
(28)

The Company had an effective tax rate of (0.21)%, (0.66)%, and (0.17)% for the years ended December 31, 2021, 2020, and 2019, respectively. The reconciliation of the statutory
federal income tax rate to the Company’s effective tax rate for the years ended December 31, 2021, 2020, and 2019 were as follows:

102

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

Tax at federal statutory rate
State tax, net of federal benefit
Stock-based compensation
Other items
Research and development credits
Net operating loss expiration
Change in valuation allowance

Effective tax rate

2021

2020

2019

21.00  %
(0.19)
44.13 
(0.16)
7.04 
(8.08)
(63.95)

(0.21) %

21.00  %
(0.49)
94.02 
(0.59)
9.74 
(14.00)
(110.34)

(0.66) %

21.00  %
(0.27)
51.45 
(4.34)
13.74 
(18.33)
(63.42)

(0.17) %

Deferred income taxes reflect the tax effects of temporary differences between the carrying amounts of assets and liabilities for financial reporting purposes and the amounts used
for income tax purposes. As of December 31, 2021 and 2020, the significant components of the Company’s deferred tax assets and liabilities were as follows:

(In thousands)
Deferred tax assets:

Net operating loss carryforwards
Stock-based compensation
Operating lease liability
Non-deductible accrued expenses, reserves and other
Research and development credits

Gross deferred tax assets
Valuation allowance
Total deferred tax assets

Deferred tax liabilities:

Acquired intangible assets
Operating lease asset
Debt issuance cost
Depreciation and amortization
Total deferred tax liabilities

Net deferred tax assets

2021

2020

$

100,836  $
5,617 
5,296 
7,259 
17,044 
136,052 
(132,162)
3,890 

— 
(2,452)
(75)
(1,363)
(3,890)

$

—  $

77,230 
230 
5,555 
4,903 
11,352 
99,270 
(92,390)
6,880 

(89)
(4,523)
— 
(2,268)
(6,880)
— 

The change in valuation allowance for deferred tax assets was as follows for the periods presented:

(In thousands)

Year Ended December 31,

2021
2020
2019

Balance at
Beginning of Year

Additions Charged to
Costs & Expenses

Additions Charged to
Other Accounts

Deductions

$

92,390  $
63,542 
49,439 

39,772  $
28,848 
14,103 

—  $
— 
— 

Balance at End of Year
132,162 
92,390 
63,542 

—  $
— 
— 

The  Company  records  a  full  valuation  allowance  of  $132.2  million  and  $92.4  million  as  of  December  31,  2021  and  2020,  respectively,  against  its  net  deferred  tax  assets.  The
Company determines its valuation allowance on deferred tax assets by considering both positive and negative evidence in order to ascertain whether it is more likely than not that
deferred  tax  assets  will  be  realized.  Realization  of  deferred  tax  assets  is  dependent  upon  the  generation  of  future  taxable  income,  if  any,  the  timing  and  amount  of  which  are
uncertain. Due to the history of losses the Company has generated in the past, the Company believes that it is not more likely than not that all of the deferred tax assets can be
realized as of December 31, 2021. Accordingly, the Company has recorded a full valuation allowance on its deferred tax assets.

The Company has federal net operating loss, which is referred to as NOL, carryforwards of approximately $444.6 million and $343.1 million as of December 31, 2021 and 2020,
respectively. The federal NOLs generated in the

103

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

years ended December 31, 2001 through 2017 began to expire in 2021, including $21.6 million that expired in 2021 and $23.0 million that will expire in 2022. NOLs originating
before January 1, 2018, are eligible to offset taxable income, if not otherwise limited under Internal Revenue Code, which is referred to as IRC, §382 limitations. NOLs generated
after December 31, 2017, have an infinite carryforward period and subject to 80% deduction limitation based upon pre-NOL deduction taxable income. The Company has California
NOL carryforwards of approximately $90.4 million and $72.9 million as of December 31, 2021 and 2020, respectively. California NOLs generated in the years ended December 31,
2008 through 2018 will begin to expire in 2028. California NOLs generated before 2008 have expired in accordance the California Revenue Taxation Code and related regulations.

The Company has federal research and development credits, which are referred to as Credits, of approximately $19.1 million and $12.0 million as of December 31, 2021 and 2020,
respectively.  In  2021,  $0.1  million  of  federal  research  and  development  credits  expired  and  the  remaining  carryforward  is  subject  to  expiration  through  2041.  The  Company  has
California Credits of approximately $13.6 million and $13.1 million as of December 31, 2021 and 2020, respectively. California Credits have an infinite carryforward period.

Utilization of the NOL and Credit carryforwards that were generated prior to January 1, 2018 may be subject to a substantial annual limitation due to ownership changes that may
have occurred or that could occur in the future, as required by IRC §382 and §383, as well as similar state provisions.

Uncertain Tax Positions

As of December 31, 2021, the Company’s total amount of unrecognized tax benefits was $15.4 million, none of which would impact the Company’s effective tax rate, if recognized.

For the years ended December 31, 2021, 2020, and 2019, the activity related to the unrecognized tax benefits were as follows:

(In thousands)
Gross unrecognized tax benefits—beginning balance
Increase related to tax positions taken during prior year
Decrease related to tax positions taken during prior year
Increase related to tax positions taken during current year
Decrease related to expiration of unrecognized tax benefit

Gross unrecognized tax benefits—ending balance

2021

2020

2019

$

$

13,338  $
697 
(148)
1,635 
(131)
15,391  $

12,782  $
131 
— 
608 
(183)
13,338  $

10,973 
— 
(164)
1,973 
— 
12,782 

The Company recognizes interest and penalties related to uncertain tax positions in income tax expense. To the extent accrued interest and penalties do not ultimately become
payable, amounts accrued will be reduced and reflected as a reduction of the provision for income taxes in the period that such determination is made. As of December 31, 2021,
the Company did not currently recognize any penalties or interest charges relating to uncertain tax positions. The Company does not anticipate the recorded reserves to change
significantly in the next 12 months.

The  Company  is  subject  to  taxation  in  the  United  States  and  various  other  state  and  foreign  jurisdictions.  Due  to  certain  tax  attribute  carryforwards,  the  tax  years  2001  to  2021
remain open to examination by the major taxing jurisdictions in which the Company is subject to tax. As of December 31, 2021, the Company was not under examination by the
Internal Revenue Service or any state or foreign tax jurisdiction.

Note 12—Segment and Geographical Information

The Company operates as one operating and reportable segment for purposes of allocating resources and evaluating financial performance.

The following table sets forth total revenue by type of service for the years ended December 31, 2021, 2020, and 2019:

(In thousands)
Marketplace

Basic, Plus, and other
Enterprise

Managed services

Total

2021

2020

2019

$

$

427,476  $
34,864 
40,457 
502,797  $

317,942  $
20,210 
35,476 
373,628  $

253,099 
15,185 
32,278 
300,562 

104

UPWORK INC.
Notes to Consolidated Financial Statements—Continued

The Company generates its revenue from talent and clients. The following table sets forth total revenue by geographic area based on the billing address of its talent and clients for
the years ended December 31, 2021, 2020, and 2019:

(In thousands)
Talent:

United States
India
Philippines
Rest of world
Total talent

Clients:

United States
Rest of world

Total clients

Total

2021

2020

2019

$

$

74,890  $
42,277 
32,918 
146,894 
296,979 

153,003 
52,815 
205,818 
502,797  $

60,861  $
33,109 
22,924 
109,805 
226,699 

107,359 
39,570 
146,929 
373,628  $

50,154 
27,369 
19,660 
90,259 
187,442 

87,241 
25,879 
113,120 
300,562 

Substantially all of the Company’s long-lived assets were located in the United States as of December 31, 2021 and 2020.

Note 13—401(k) Plan

The Company offers the Upwork Retirement Savings Plan, which is referred to as the Retirement Plan, a defined contribution plan that allows employees to contribute a portion of
their  salary,  subject  to  the  annual  limits.  Under  the  Retirement  Plan,  eligible  employees  may  defer  a  portion  of  their  pretax  salaries,  but  not  more  than  the  statutory  limits.  The
Retirement  Plan  provides  for  a  discretionary  employer  cash  matching  contribution.  The  Company  makes  matching  cash  contributions  equal  to  50%  of  each  dollar  contributed,
subject to a maximum contribution of $5,000 annually per participant. The Company’s total expense for the matching contributions was $2.5 million, $2.5 million, and $2.0 million for
the years ended December 31, 2021, 2020, and 2019, respectively.

105

Item 9. Changes In and Disagreements With Accountants on Accounting and Financial Disclosure.

None.

Item 9A. Controls and Procedures.

Evaluation of Disclosure Controls and Procedures

Our management, with the participation of our Chief Executive Officer and Chief Financial Officer, evaluated the effectiveness of our disclosure controls and procedures as defined
in Rules 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended, which we refer to as the Exchange Act, as of December 31, 2021. Our Chief Executive
Officer and Chief Financial Officer concluded that, as of December 31, 2021, our disclosure controls and procedures were effective to provide reasonable assurance that information
we are required to disclose in the reports we file or submit under the Exchange Act is accumulated and communicated to our management, including our Chief Executive Officer and
Chief  Financial  Officer,  as  appropriate  to  allow  timely  decisions  regarding  required  disclosures,  and  is  recorded,  processed,  summarized,  and  reported  within  the  time  periods
specified in the rules and forms of the SEC.

Management’s Report on Internal Control Over Financial Reporting

Our management, including our Chief Executive Officer and Chief Financial Officer, is responsible for establishing and maintaining adequate internal control over financial reporting
(as  defined  in  Rule  13a-15(f)  under  the  Exchange  Act).  Our  management  conducted  an  assessment  of  the  effectiveness  of  our  internal  control  over  financial  reporting  as  of
December  31,  2021  based  on  the  criteria  set  forth  in  Internal  Control—Integrated  Framework  (2013)  issued  by  the  Committee  of  Sponsoring  Organizations  of  the  Treadway
Commission (2013 framework). Based on that assessment, our management concluded that our internal control over financial reporting was effective as of December 31, 2021.

PricewaterhouseCoopers LLP, our independent registered public accounting firm, has audited the effectiveness of our internal control over financial reporting as of December 31,
2021. This report appears on page 70.

Changes in Internal Control over Financial Reporting

There were no changes to our internal control over financial reporting that occurred during the quarter ended December 31, 2021 that have materially affected, or are reasonably
likely to materially affect, our internal control over financial reporting.

Inherent Limitations on Effectiveness of Internal Controls

An  effective  internal  control  system,  no  matter  how  well  designed,  has  inherent  limitations,  including  the  possibility  of  human  error  or  overriding  of  controls,  and  therefore  can
provide  only  reasonable  assurance  with  respect  to  reliable  financial  reporting.  Because  of  its  inherent  limitations,  our  internal  control  over  financial  reporting  may  not  prevent  or
detect  all  misstatements,  including  the  possibility  of  human  error,  the  circumvention  or  overriding  of  controls,  or  fraud.  Effective  internal  controls  can  provide  only  reasonable
assurance with respect to the preparation and fair presentation of financial statements.

Item 9B. Other Information.

None.

Item 9C. Disclosure Regarding Foreign Jurisdictions that Prevent Inspections.

None.

PART III

Item 10. Directors, Executive Officers and Corporate Governance.

The information required by this item will be included in our Proxy Statement for the 2022 Annual Meeting of Stockholders, which we refer to as the Proxy Statement, to be filed with
the SEC within 120 days of the fiscal year ended December 31, 2021, and is incorporated herein by reference.

Item 11. Executive Compensation.

The information required by this item will be included in our Proxy Statement to be filed with the SEC, within 120 days of the year ended December 31, 2021, and is incorporated
herein by reference.

106

Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters.

The information required by this item will be included in our Proxy Statement to be filed with the SEC, within 120 days of the year ended December 31, 2021, and is incorporated
herein by reference.

Item 13. Certain Relationships and Related Transactions, and Director Independence.

The information required by this item will be included in our Proxy Statement to be filed with the SEC, within 120 days of the year ended December 31, 2021, and is incorporated
herein by reference.

Item 14. Principal Accountant Fees and Services.

The information required by this item will be included in our Proxy Statement to be filed with the SEC, within 120 days of the year ended December 31, 2021, and is incorporated
herein by reference.

107

PART IV

Item 15. Exhibits and Financial Statement Schedules.

(a) The following documents are filed as part of this report:

(1) Financial Statements.

Our consolidated financial statements are listed in the “Index to Consolidated Financial Statements” under Part II, Item 8 of this Annual Report on Form 10-K.

(2) Financial Statement Schedules.

All schedules are omitted because they are not applicable or because the required information is shown in the consolidated financial statements and notes.

(3) Exhibits.

Exhibit Index

Exhibit

Number

3.1

3.2

4.1

4.2

4.3

4.4

4.5

4.6

10.1*

10.2*

10.3*

10.4*

10.5*

10.6*

10.7*

10.8*

10.9*

10.10*

10.11*

10.12*

10.13*

10.14*

10.15*

Exhibit Title
Restated Certificate of Incorporation.

Amended and Restated Bylaws.

Form of Common Stock Certificate.

Amended and Restated Investors’ Rights Agreement, dated August 19, 2014, by and among Upwork and
certain security holders of Upwork, as amended.

Warrant, dated May 1, 2018, by and between Upwork and Tides Foundation.

Description of Securities Registered Under Section 12 of the Exchange Act.

Indenture, dated as of August 10, 2021, between Upwork Inc. and Wells Fargo Bank, National Association,
as trustee.

Form of 0.25% Convertible Senior Notes due 2026 (included in Exhibit 4.5).

Form of Indemnification Agreement by and between Upwork and each of its directors and executive
officers.

oDesk 2004 Stock Plan, as amended, and forms of equity agreements thereunder.

2014 Equity Incentive Plan, as amended, and forms of equity agreements thereunder.

2018 Equity Incentive Plan and forms of award agreements thereunder.

2018 Employee Stock Purchase Plan and enrollment forms thereunder.

Offer Letter, dated February 25, 2015, by and between Upwork and Elizabeth Nelson.

Offer Letter, dated August 3, 2018, by and between Upwork and Gary Steele.

Upwork Performance Bonus Plan.

Offer Letter, dated June 17, 2019 by and between Upwork and Leela Srinivasan.

Change in Control and Severance Agreement, dated December 8, 2019, by and between Upwork and
Hayden Brown.

Amended and Restated Offer Letter, dated December 8, 2019, by and between Upwork and Hayden
Brown.

Change in Control and Severance Agreement, dated May 29, 2018, by and between Upwork and Randoll
Eric Gilpin.

Amended and Restated Offer Letter, dated May 29, 2018, by and between Upwork and Randoll Eric Gilpin.

Offer Letter, dated July 10, 2020, by and between Upwork Inc. and Jeff McCombs.

Change in Control and Severance Agreement, dated August 4, 2020, by and between Upwork Inc. and
Jeff McCombs.

108

Incorporated by Reference

File No.

Exhibit

Filing Date

Filed Herewith

Form

10-Q

8-K

S-1

S-1

S-1

8-K

8-K

S-1

S-1

S-1

S-1

S-1

S-1

S-1

10-Q

10-Q

001-38678

001-38678

333-227207

333-227207

333-227207

001-38678

001-38678

333-227207

333-227207

333-227207

333-227207

333-227207

333-227207

333-227207

001-38678

001-38678

X

3.1

3.1

4.1

4.2

4.4

4.1

4.2

10.1

10.2

10.3

10.4

10.5

10.13

10.16

10.2

10.2

10.8

November 8, 2018

December 22, 2020

September 6, 2018

September 6, 2018

September 6, 2018

August 10, 2021

August 10, 2021

September 6, 2018

September 6, 2018

September 6, 2018

September 6, 2018

September 6, 2018

September 6, 2018

September 6, 2018

May 8, 2019

August 7, 2019

March 2, 2020

10-K

001-38678

10-K

001-38678

10.11

March 2, 2020

10-Q

10-Q

10-Q

001-38678

001-38678

001-38678

10-Q

001-38678

10.1

10.2

10.1

10.2

August 4, 2020

August 4, 2020

November 4, 2020

November 4, 2020

10-K

10-Q

8-K

001-38678

    001-38678

001-38678

10.21

10.1

10.1

February 24, 2021

May 4, 2021

August 10, 2021

10.16*

10.17*

10.18

10.19

21.1

23.1

24.1

31.1

31.2

32.1#

32.2#

101.INS

101.SCH
101.CAL
101.DEF
101.LAB
101.PRE
104

Offer Letter, dated October 13, 2020, by and between Upwork Inc. and Anilu Vazquez-Ubarri.

Stock Option Agreement, dated January 18, 2021, by and between Upwork Inc. and Hayden Brown.

Form of Capped Call Transaction Confirmation.

Lease Agreement, dated May 14, 2014, by and between Upwork and CLPF, as amended.

List of Subsidiaries.

Consent of PricewaterhouseCoopers LLP, independent registered public accounting firm.

Power of Attorney (included on signature page to Annual Report).

Certification of Principal Executive Officer Pursuant to Rules 13a-14(a) and 15d-14(a) under the Securities
Exchange Act of 1934, as Adopted Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.

Certification of Principal Financial Officer Pursuant to Rules 13a-14(a) and 15d-14(a) under the Securities
Exchange Act of 1934, as Adopted Pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.

Certification of Principal Executive Officer Pursuant to 18 U.S.C. Section 1350, as Adopted Pursuant to
Section 906 of the Sarbanes-Oxley Act of 2002.

Certification of Principal Financial Officer Pursuant to 18 U.S.C. Section 1350, as Adopted Pursuant to
Section 906 of the Sarbanes-Oxley Act of 2002.

Inline XBRL Instance Document - the instance document does not appear in the interactive data file
because its XBRL tags are embedded within the inline XBRL document.
Inline XBRL Taxonomy Extension Schema Document.
Inline XBRL Taxonomy Extension Calculation Linkbase Document.
Inline XBRL Taxonomy Extension Definition Linkbase Document.
Inline XBRL Taxonomy Extension Label Linkbase Document.
Inline XBRL Taxonomy Extension Presentation Linkbase Document.
Cover Page Interactive Data File - the cover page from the Registrant’s Annual Report on Form 10-K for
the year ended December 31, 2021 is formatted in Inline XBRL.

*    Indicates a management contract or compensatory plan.

X

X

X

X

X

X

X

X

X
X
X
X
X
X

X

#    This certification is deemed not filed for purposes of Section 18 of the Exchange Act, or otherwise subject to the liability of that section, nor shall it be deemed incorporated by reference into any filing under the Securities

Act or the Exchange Act.

109

Item 16. Form 10-K Summary.

None.

110

Pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this Annual Report on Form 10-K to be
signed on its behalf by the undersigned, thereunto duly authorized.

SIGNATURES

Date: February 15, 2022

Upwork Inc.
By:

POWER OF ATTORNEY

/s/ Hayden Brown
Hayden Brown
President and Chief Executive Officer

KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature appears below hereby constitutes and appoints Hayden Brown and Jeff McCombs, and each of
them, as his or her true and lawful attorneys-in-fact, proxies, and agents, each with full power of substitution, for him or her in any and all capacities, to sign any and all amendments
to this Annual Report on Form 10-K, and to file the same, with all exhibits thereto and other documents in connection therewith, with the Securities and Exchange Commission,
granting unto said attorneys-in-fact, proxies, and agents full power and authority to do and perform each and every act and thing requisite and necessary to be done in connection
therewith, as fully for all intents and purposes as he might or could do in person, hereby ratifying and confirming all that said attorneys-in-fact, proxies, and agents, or their or his or
her substitute or substitutes, may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, this Annual Report on Form 10-K has been signed below by the following persons on behalf of
the Registrant in the capacities and on the dates indicated.

Signature

/s/ Hayden Brown
Hayden Brown

/s/ Jeff McCombs
Jeff McCombs

/s/ Gregory C. Gretsch
Gregory C. Gretsch

/s/ Kevin Harvey
Kevin Harvey

/s/ Thomas Layton
Thomas Layton

/s/ Elizabeth Nelson
Elizabeth Nelson

/s/ Leela Srinivasan
Leela Srinivasan

/s/ Gary Steele
Gary Steele

/s/ Anilu Vazquez-Ubarri
Anilu Vazquez-Ubarri

Title

President, Chief Executive Officer, and Director
(Principal Executive Officer)

Chief Financial Officer
(Principal Financial and Accounting Officer)

Director

Director

Director

Director

Director

Director

Director

111

Date

February 15, 2022

February 15, 2022

February 15, 2022

February 15, 2022

February 15, 2022

February 15, 2022

February 15, 2022

February 15, 2022

February 15, 2022