Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.

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Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Upwork
Q3 Investor
Presentation
October 2021

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Safe
Harbor                                       This presentation and the accompanying oral commentary contain "forward-looking" statements based on the beliefs and assumptions of Upwork Inc.
                                             (the "Company") and on information currently available to the Company. Forward-looking statements include all statements other than statements of
                                             historical fact contained in this presentation, including information or predictions concerning the future of the Company's business, anticipated events and
                                             trends, potential growth opportunities, competitive position, technological and market trends, industry environment, potential market opportunities, the
                                             economy and other future conditions. Any forward-looking statements made herein or made elsewhere by the Company are made solely based on
                                             information available to the Company as of the date hereof and based only on the Company's current beliefs, expectations and assumptions. As such,
                                             they are subject to inherent uncertainties, known and unknown risks and changes in circumstances that are difficult to predict and in many cases outside
                                             the Company's control, and you should not rely on such forward-looking statements. The Company makes no representation that the projected results will
                                             be achieved, and actual results may differ materially from the Company's expectations. Furthermore, the Company does not undertake any obligation to
                                             update or revise any forward-looking statements, to conform these statements to actual results or to make changes in the Company's expectations,
                                             except as required by law. In addition, any statements regarding the current and future impacts of the COVID-19 pandemic on our business and current
                                             and future impacts of actions we have taken in response to the COVID-19 pandemic are forward-looking statements and related to matters that are
                                             beyond our control and changing rapidly. Additional information regarding these and other risks and uncertainties that could cause actual results to differ
                                             materially from the Company's expectations is included under the caption "Risk Factors" in the Company's Quarterly Report on Form 10-Q for the three
                                             months ended September 30, 2021 filed when filed and the Company's other SEC filings.

                                             This presentation also contains estimates, forecasts and other statistical data made by independent parties and by the Company relating to market size
                                             and growth and other data about the Company's industry. This data involves a number of assumptions and limitations, and you are cautioned not to give
                                             undue weight to such estimates. In addition, projections, assumptions and estimates of the Company's future performance and the future performance of
                                             the markets in which the Company operates are necessarily subject to a high degree of uncertainty and risk.

                                             Moreover, neither the Company nor any other person makes any representation or warranty as to the accuracy or completeness of the information herein.
                                             This presentation is made solely for informational purposes.

                                             All third-party trademarks, including names, logos and brands, referenced by the Company in this presentation are property of their respective owners.
                                             All references to third-party trademarks are for identification purposes only and shall be considered nominative fair use under trademark law.

                                             In addition to the GAAP financials, this presentation includes certain non-GAAP financial measures. The non-GAAP measures have limitations as analytical
                                             tools, and you should not consider them in isolation or as a substitute for the most directly comparable financial measures prepared in accordance with
                                             GAAP. There are a number of limitations related to the use of these non-GAAP financial measures versus their nearest GAAP equivalents. Other
                                             companies, including companies in the Company's industry, may calculate non-GAAP financial measures differently or may use other measures to
                                             evaluate their performance, all of which could reduce the usefulness of non-GAAP financial measures as tools for comparison. The Company urges you to
                                             review the reconciliation of non-GAAP financial measures to the most directly comparable GAAP financial measures set forth in the Appendix, and not rely
                                             on any single financial measure to evaluate the Company's business.

© 2021 Upwork Inc.   Q3’21 Investor Presentation       October 2021                                                                                                                                         2
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Non-GAAP
Financial
Measures
                                             To supplement our condensed consolidated financial statements, which are prepared in accordance with GAAP, we present non-GAAP cost of revenue
                                             (and as a percentage of revenue), non-GAAP marketplace cost of revenue, non-GAAP managed services cost of revenue, non-GAAP gross profit (and as a
                                             percentage of revenue), non-GAAP operating expenses (total and each line item, and total and each non-GAAP operating expense item as a percentage of
                                             revenue), non-GAAP income (loss) from operations (and as a percentage of revenue), non-GAAP net income (loss) (and as a percentage of revenue and on
                                             a per share basis), non-GAAP gross margin (total and for marketplace and managed services), and adjusted EBITDA in this presentation. Our use of
                                             non-GAAP financial measures has limitations as an analytical tool, and these measures should not be considered in isolation or as a substitute for analysis
                                             of financial results as reported under GAAP.

                                             We use these non-GAAP financial measures in conjunction with financial measures prepared in accordance with GAAP for planning purposes, including in
                                             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. These measures provide consistency and comparability with past financial performance, facilitate period-to-period comparisons
                                             of core operating results, and also facilitate comparisons with other peer companies, many of which use similar non-GAAP financial measures to
                                             supplement their GAAP results. In addition, adjusted EBITDA is widely used by investors and securities analysts to measure a company’s operating
                                             performance. We exclude the following items from one or more of our non-GAAP financial measures: stock-based compensation expense (non-cash
                                             expense calculated by companies using a variety of valuation methodologies and subjective assumptions), depreciation and amortization (non-cash
                                             expense), interest expense, other (income) expense, net, income tax (benefit) provision, and, if applicable, certain other non-cash transactions.

                                             Investors are cautioned that there are material limitations associated with the use of non-GAAP financial measures as an analytical tool. In particular,
                                             (1) stock-based compensation expense 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, (2) although depreciation and amortization expense are non-cash charges, the assets
                                             subject to depreciation and amortization 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, and (3) 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; (c) tax payments that may represent a reduction in cash available to us; or (d) expense from our common stock warrant
                                             issued to the Tides Foundation, which is recurring and will be reflected in our financial results for the foreseeable future. The non-GAAP measures we use
                                             may be different from non-GAAP financial measures used by other companies, limiting their usefulness for comparison purposes. We compensate for
                                             these limitations by providing specific information regarding the GAAP items excluded from these non-GAAP financial measures. A reconciliation of these
                                             non-GAAP measures has been provided in the financial statement tables included in this presentation and investors are encouraged to
                                             review the reconciliation.

© 2021 Upwork Inc.   Q3’21 Investor Presentation       October 2021                                                                                                                                         3
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Our Mission

Create
economic
opportunities
so people
have better
lives.
© 2021 Upwork Inc. Proprietary and
                                 Q3’21
                                   confidential.
                                       Investor Do
                                                Presentation
                                                   not distribute.   October
                                                                      Q2’21 2021
                                                                             Investor Presentation   July, 2021   © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Our Vision

Independent
talent at the
heart of every
business.

© 2021 Upwork Inc. Proprietary and
                                 Q3’21
                                   confidential.
                                       Investor Do
                                                Presentation
                                                   not distribute.   October
                                                                      Q2’21 2021
                                                                             Investor Presentation   July, 2021   © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Uniquely
Positioned to
Succeed

    Massive TAM with                                    Largest work                        Deep and expanding   Multiple growth   Proven and
    secular tailwinds                                   marketplace at scale1               competitive moats    opportunities     experienced
                                                                                                                                   management team

1
    As measured by gross services volume (GSV). See appendix for the definition of gross services volume.

© 2021 Upwork Inc.        Q3’21 Investor Presentation       October 2021                                                                             6
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Creating a Massive and
Growing Opportunity

                         ~225
                         Million                             x                 ~$5,850                =   $1.3T
                     Estimated number of                                   Average
                     global remote                                         freelancer GSV 2
                     knowledge workers 1

                                                                                                          Upwork Opportunity

1
    2021 estimate from Gartner - Forecast Analysis: Remote Workers Forecast, Worldwide August 2020.
2
    TTM as of Dec. 31, 2020.

© 2021 Upwork Inc.       Q3’21 Investor Presentation   October 2021                                                            7
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Upwork Is the                                                     Talent Marketplace TM
Most Comprehensive
Work Marketplace                                                     Enterprise Suite

Multiple ways to Upwork = the “always on”                         Bring Your Own Talent
solution for companies hiring and managing
freelancer programs at scale
                                                                         Payroll

                                                                    Direct Contracts

                                                                    Project Catalog TM

                                                                     Talent Scout TM

                                                                     ...What’s Next?

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                           8
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Featuring the Most
Robust Community of
Clients and Freelancers

10,000+ skills

    73% of talent have college degrees 1

50+ categories with $10M+ in GSV 2

~40% of clients hired in multiple categories 2

1
    February 2021 Upwork internally conducted survey.
2
    Based on the trailing 12-month period ending September 30, 2021.
© 2021 Upwork Inc.        Q3’21 Investor Presentation   October 2021
Upwork Q3 Investor Presentation - October 2021 - Investor Relations | Upwork Inc.
Freelancer Stages of Adoption

                                                                                                                4         Freelancer-First
                                                                                                                          Companies change view from “why
                                                                                                                          Upwork?” to “why not Upwork?”

                                                                                             3              Scaling
                                                                                                            Companies make investments to leverage
    Customer Value

                                                                                                            freelancers as core to the way they get work done

                                                                       2    Hybrid

                                     1                                      Freelancers complement FTEs and become
                                                                            an option for additional projects

                                Project
                                Freelancers evaluated and vetted on a
                                project-by-project basis to solve specific
                                needs on a one-off basis

                                                                            Freelancer Adoption Over Time

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                                 10
Our Goal: 100%
of businesses will
have freelancers
on their teams in
the future
© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021   11
Generating Abundant
Growth Opportunities
Expected horizon for significant value creation

   Near Term                                                      Mid Term                                Long Term
  Brand Awareness

   Acquisition / Retention

   Enterprise

   Share of Wallet

   Product Line Diversification

                                                                  Internationalization and Localization

                                                                  Talent Services

                                                                  Product Integrations

                                                                                                          Take Rate Expansion

  Opportunistic M&A

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                 12
The Race to Win the $1.3T
Work Marketplace Opportunity

Platform-first service model                                                     Hybrid service model                      Traditional staffing service model

                                                                                 Work Marketplace

                                                                   Vetting      Platform &   Shortlisting   Sales
                                                                   & talent     payments     & success
                                                                   management                management

                                                                   Match &      Payroll      B2B            Talent pool               Regional Staffing Cos
                                                                   reputation                marketing

                                                                                                                                       Local Staffing Cos

                                                                  “Platform when you want it – people when you don’t.”

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                             13
Three Talent Plans
  Freelancer                                                      Freelancer                                 Agency
  Basic                                                           Plus                                       Plus

  •   Access to quality projects                                  Includes all Freelancer Basic features +   Includes all Freelancer Plus features +

  •   Quickly apply and get hired                                 •   Customized profile URL                  •   Unlimited team members

  •   Get paid securely and on time                               •   Insight into competitor                •   Shared Connects functionality
                                                                      bid ranges

                                                                  •   Monthly Connects package*
                                                                      *not included in Agency Plus

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                        14
Four Client Plans
  Basic                                               Plus                            Enterprise:                      Enterprise:
                                                                                      Standard                         Compliance

  •   Access to a global                              Includes all Basic features +   Includes all Plus features +     Includes all Enterprise: Standard features +

      talent pool                                     •   Invites to talent           •   Custom reporting             •   Compliance services
  •   Safe and easy payments                          •   Featured Jobs upgrade       •   API access                   •   Worker classification
  •   Payment protection plan                         •   Connects package            •   Expert-vetted talent pools   •   Misclassification
  •   Customer support                                                                    and talent clouds                indemnification
                                                      •   Recruiting services
                                                                                      •   SSO / permissions            •   Work protection program

                                                                                      •   Purchase order
                                                                                          management

                                                                                      •   Consolidated invoicing
                                                                                          and billing

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                                       15
Creating a Virtuous Cycle
   Value for Freelancers                                          Value for Clients                                  Value for Upwork
   Find work quickly                                              Quality talent                                     This engine results in:
   Access to quality, flexible projects from                       Global access to a verified Virtual Talent Bench™   Highly sticky double opt-in platform with
   our global network                                             across categories and price points                 long-term relationships and recurring use, leading
                                                                                                                     to increasing scale and recurring revenue
   Get paid on time                                               Fast access to talent
   Receive security and peace of mind with                        Receive proposals within minutes;
   Upwork Payment Protection                                      3 days average time to contract
                                                                                                                             More                     More skills /
                                                                                                                       freelancers                    categories
   Build reputation                                               Cost-effective projects
   Establish long-term credibility and relationships              Take hiring budgets further with average 50%
   with roster of clients                                         savings vs. hiring locally                                                                          Cross-
                                                                                                                                                                      selling
   Growth opportunities                                           Work efficiently, effectively
                                                                                                                     Increased                             More
   Insights on in-demand skills and emerging areas                End-to-end suite of workflow tools                                                        clients
                                                                                                                          GSV

   Flexibility                                                    Flexibility
                                                                                                                                      More / bigger
   Expanding number of ways to Upwork                             Expanding number of ways to Upwork                                    projects

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                                                 16
Infinite Personas and Categories
                                                                                                                                     Growth through breadth
                                                                                                                                                              ∞

                                     Tech & Product Lead                    Marketing & Creative Lead            Operations Lead
                                     Example: VP, Engineering               Example: VP, Marketing               Example: COO

                                    • Build and maintain my website         • Augment my design staff             • Recruit and manage my customer
                                                                                                                   support operations
                                    • Build and maintain my mobile app      • Translate my marketing assets
                                                                                                                 • Recruit and manage a skilled tech
    Growth through depth

                                    • Do QA testing on my product           • Build my new landing page            support team

                                    • Augment or replace my internal        • Develop my campaign strategy       • Let me outsource my accounting to
                                      UI / UX team                                                                 a trusted accountant
                                                                            • Develop my social media strategy
                                    • Maintain a safe and secure dev                                             • Provide me project-based
                                      environment for me                    • Execute my social media strategy     accounting support

                                    •    ...                                •   ...                              •   ...
                           ∞

© 2021 Upwork Inc.             Q3’21 Investor Presentation   October 2021                                                                                         17
Key Marketing and
Acquisition Growth
Levers for 2021 and
Beyond

                                 1                                  2                               3                             4
                             Launched our work                    Expanding paid                 Improving conversion        Automating and scaling
                             marketplace marketing                acquisition reach by:          rates by:                   SEM and social through
                             efforts to build                                                                                 proprietary bidding tool:
                                                                  • Expanding SEM keywords       • Matching intent to best
                             awareness and                          and mobile SEM conversion      product lines             • Increasing registration-to-Start
                             drive demand                           optimizations                                              conversions through better
                                                                                                 • Improving CLTV model        client onboarding
                                                                  • Growing international          to optimize client
                                                                    presence ~30% YoY via          keyword bidding           • Aggressively supporting
                                                                    keyword expansion globally                                 Enterprise Sales land and
                                                                                                                               expand efforts
                                                                  • Shifting to new brand
                                                                    messaging across channels                                • Optimizing reactivation
                                                                    to improve CTRs                                            and retention efforts by moving
                                                                                                                               to more holistic marketing
                                                                                                                               automation

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                                   18
The
Enterprise                                                        + Many more globally
Opportunity
                                                                              250+ employee US-based companies

                                                                       51K    assigned to sales teams
                                                                              (both inbound and outbound)

                                                                         8K   Target ideal customer
                                                                              profile (ICP) accounts

                                                                              Target ICP customers

                                                                     1,600    with spend currently
                                                                              in the Marketplace

                                                                                                        1,000 accounts
                                                                                                        could deliver
                                                                      200+
                                                                              Current
                                                                              Enterprise
                                                                              clients
                                                                                                        $1-2B in GSV
© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                      19
Commitment
to Strong
ESG Practices
    Focus Area                               Initiatives                                                                        Achievements to Date

    Environment                             •   Reducing emissions by limiting our physical corporate                           ✓ Enabled team members to avoid over 1 million commuting
                                                office footprint through our remote-first working model                             miles in 2019
                                            •   Reducing unnecessary commuting and travel                                       ✓ Achieved carbon neutrality for 2019 and 2020
                                                                                                                                ✓ Committed to remaining carbon neutral going forward
                                            •   Purchasing carbon offsets that promote environmental
                                                sustainability

    Social                                  •   Building a more robust diversity, inclusion and belonging                       ✓ 50% of Board is female
                                                (DIBs) infrastructure                                                           ✓ 3 of our 8 directors are from underrepresented communities 1
                                            •   Leveraging data to inform strategic talent process decisions
                                            •   Preparing quantitative disclosures to demonstrate our progress on
                                                DIBs-related initiatives

    Governance                              •   Evolving Board and governance practices to reflect our                           ✓ Implemented majority-vote standard for director elections and
                                                maturation as a public company                                                   adopted proxy access
                                            •   Focusing on and responding to stockholder feedback                              ✓ The Board’s Nominating and Governance Committee oversees all
                                                                                                                                 ESG functions
                                            •   Acting to protect and grow long-term stockholder value

1
    As defined under California law AB 979, underrepresented communities includes certain racial, ethnic, and LGBT identities.

© 2021 Upwork Inc.        Q3’21 Investor Presentation      October 2021                                                                                                                           20
Our Winning
   Strategy                                                       1   Innovating the work marketplace

                                                                  2   Becoming a world-renowned brand

                                                                  3   Augment SMB by winning
                                                                      the enterprise

                                                                  4   Building an extraordinary hybrid
                                                                      team of employees and freelancers

                                                                  5   Investing aggressively for long-term
                                                                      value creation

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                              21
Financial
Highlights

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021
Upwork
at a Glance
 As of September 30, 2021

752K                              $4,375
 Active Clients                   GSV per Active Client

    Gross Services Volume (GSV) ($M)                                           Revenue ($M)                                              Adjusted EBITDA ($M)

                     21%↑                                     38%↑                      24%↑                              32%↑                     89%↑                 23%↑

                        $2,524                                                                 $374
                                                                                               $374

                                                                     $904
         $2,087                                                                  $301
                                                                                 $301                                                                 $14.0
                                                      $655                                                                       $128
                                                                                                                    $97                                                        $8.2
                                                                                                                                            $7.4                $6.7

          2019          2020                          Q3’20          Q3’21       2019          2020                Q3’20         Q3’21     2019       2020      Q3’20          Q3’21

Note: Adjusted EBITDA is a non-GAAP measure. See appendix for the definition of GSV, Active Clients, and GSV per Active Client.

© 2021 Upwork Inc.          Q3’21 Investor Presentation         October 2021                                                                                                           23
Strong Active
                                                                                                                                                        YoY Growth      TTM Active Clients

Client Growth
                            700k
                                                                                                                                                                           30%

                                                                                                                                                  27%
                            600k
                                                                                                                                                                           25%
                                                                                                                                        25%                      25%

                            500k
                                                                                                                                                                           20%
     TTM Active Clients 1

                                                                                                                                                                                     YoY Growth
                            400k                                                                                              17%
                                                                                                                                                                           15%

                            300k
                                                                                                                    12%
                                                                                                                                                                           10%
                                     10%                  10%         10%
                            200k                                                      9%                  9%

                                                                                                7%
                                                                                                                                                                           5%
                            100k

                                                                                                                                                                           0%
                            0k

                                   Q1-2019          Q2-2019         Q3-2019         Q4-2019   Q1-2020   Q2-2020   Q3-2020   Q4-2020   Q1-2021   Q2-2021       Q3-2021
1
    See appendix for the definition of Active Clients.

© 2021 Upwork Inc.                    Q3’21 Investor Presentation    October 2021                                                                                                                 24
GSV Per
                                                                                                                                             TTM Avg GSV per Active Client(1)         YoY Growth

Active Client
is Increasing
                               $4,000                                                                                                                                                    15%

                                          14%

                               $3,750                          12%                                                                                                              12%

                                                                           10%                                                                                                           10%
     GSV per Active Client 1

                                                                                          9%        9%

                                                                                                                                                                                                   YoY Growth
                                                                                                                                                            8%
                               $3,500

                                                                                                              6%
                                                                                                                                                                                         5%

                               $3,250
                                                                                                                        4%
                                                                                                                                  3%
                                                                                                                                            2%

                               $3,000                                                                                                                                                    0%

                                        Q1-2019           Q2-2019        Q3-2019        Q4-2019   Q1-2020   Q2-2020   Q3-2020   Q4-2020   Q1-2021       Q2-2021          Q3-2021
1
    See appendix for the definition of GSV per Active Client.

© 2021 Upwork Inc.                         Q3’21 Investor Presentation   October 2021
Our Compelling
Margin Structure                                                     % of Revenue      FY2018   FY2019   FY2020   YTD2021   LT Target

•   High and expanding gross margins
                                                                     Marketplace       75%      77%      78%      78%       80-85%
                                                                     Gross Margin 1
•   Industry-leading investment levels in R&D
    to extend competitive moats
                                                                     Managed           17%      17%      19%      20%       20%
•   Opportunities for leverage in R&D and G&A                        Services
                                                                     Gross Margin 2
•   Will invest aggressively in sales and marketing
    to drive growth and maximize economic                            Total Gross       68%      71%      72%      73%       80-85%
    value added                                                      Margin

                                                                     R&D               21%      19%      20%      20%       15-20%
Notes:
1
  Marketplace gross margin is defined as total gross                  S&M               28%      31%      34%      34%       20-25%
profit, excluding revenue from Managed Services and
cost of freelancer services to deliver Managed
Services, divided by Marketplace revenue.
                                                                     G&A               16%      18%      15%      14%       8-10%
2
 Managed Services gross margin is defined as
Managed Services revenue less cost of freelancer
services to deliver Managed Services, divided by                     Transaction       2%       1%       1%       1%        1-2%
Managed Services revenue.
                                                                     Losses
Numbers are non-GAAP. Non-GAAP here excludes
SBC, amortization, and non-cash charitable donations.
All numbers reflect depreciation expense, except for                  Adjusted EBITDA   1%       2%       4%       6%        30-35%
Adjusted EBITDA.

© 2021 Upwork Inc.     Q3’21 Investor Presentation    October 2021                                                                      26
GAAP to Non-GAAP                                                          $ and share counts in millions
Reconciliation                                                            Percentages and per share data as stated

                                                                          Q3 2021                             Q3 2020                             9 Months 2021   9 Months 2020
 GAAP Net Loss                                                           (9.3)                               (2.7)                               (33.7)           (23.8)

 Stock-based compensation expense                                        13.9                                6.9                                 38.7             19.5

 Depreciation and amortization                                           2.4                                 2.7                                 8.2              7.4

 Interest expense                                                        0.7                                 0.2                                 1.1              0.6

 Other (income) expense, net                                             0.2                                 (0.5)                               0.2              -

 Income tax provision                                                    -                                   -                                   0.1              0.1

 Tides Foundation common stock warrant expense                           0.2                                 0.2                                 0.6              0.6

 Impairment expense                                                      -                                   -                                   7.4              -

 Non-GAAP Adjusted EBITDA                                                8.2                                 6.7                                 22.4             4.5

 Marketplace cost of revenue, GAAP                                       26.7                                19.5                                75.3             54.2

 Stock-based compensation                                                (0.2)                               (0.2)                               (0.6)            (0.6)

 Marketplace cost of revenue, non-GAAP                                   26.5                                19.3                                74.7             53.6

 Marketplace gross margin, non-GAAP (%)                                  77%                                 78%                                 78%              78%

Note: Figures have been rounded. Marketplace gross margin is using Marketplace revenue and total cost of revenue less Managed Services cost of revenue.
Managed Services gross margin is using Managed Services revenue and Managed Services cost of revenue.                                                                             27
GAAP to Non-GAAP                                                          $ and share counts in millions
Reconciliation (Cont.)                                                    Percentages and per share data as stated

                                                                          Q3 2021                             Q3 2020                             9 Months 2021   9 Months 2020
 Managed Services cost of revenue, GAAP                                  8.2                                 7.1                                 23.2             21.3

 Managed Services cost of revenue, non-GAAP                              8.2                                 7.1                                 23.2             21.3

 Managed Services gross margin, non-GAAP (%)                             21%                                 19%                                 20%              19%

 Cost of revenue, GAAP                                                   34.9                                26.6                                98.5             75.5

 Stock-based compensation                                                (0.2)                               (0.2)                               (0.6)            (0.6)

 Total cost of revenue, non-GAAP                                         34.7                                26.4                                97.9             74.9

 Total gross margin, non-GAAP (%)                                        73%                                 73%                                 73%              72%

 Research and development, GAAP                                          30.9                                20.8                                85.6             60.7

 Stock-based compensation                                                (4.0)                               (2.6)                               (11.3)           (7.3)

 Research and development, non-GAAP                                      26.8                                18.3                                74.3             53.4

 Sales and marketing, GAAP                                               43.2                                33.6                                128.6            98.7

 Stock-based compensation                                                (1.5)                               (1.2)                               (4.4)            (3.5)

 Sales and Marketing, non-GAAP                                           41.7                                32.4                                124.3            95.2

Note: Figures have been rounded. Marketplace gross margin is using Marketplace revenue and total cost of revenue less Managed Services cost of revenue.
Managed Services gross margin is using Managed Services revenue and Managed Services cost of revenue.                                                                             28
GAAP to Non-GAAP                                                          $ and share counts in millions
Reconciliation (Cont.)                                                    Percentages and per share data as stated

                                                                          Q3 2021                             Q3 2020                             9 Months 2021   9 Months 2020
 General and administrative, GAAP                                        26.1                                18.0                                82.0             53.0

 Stock-based compensation                                                (8.2)                               (2.9)                               (22.4)           (8.2)

 Amortization of intangible assets                                       -                                   (0.7)                               (0.7)            (1.3)

 Tides Foundation common stock warrant expense                           (0.2)                               (0.2)                               (0.6)            (0.6)

 Impairment expense                                                      -                                   -                                   (7.4)            -

 General and administrative, non-GAAP                                    17.7                                14.3                                51.0             42.9

 Loss from operations, GAAP                                              (8.3)                               (3.0)                               (32.4)           (23.1)

 Stock-based compensation                                                13.9                                6.9                                 38.7             19.5

 Amortization of intangible assets                                       -                                   0.7                                 0.7              1.3

 Tides Foundation common stock warrant expense                           0.2                                 0.2                                 0.6              0.6

 Impairment expense                                                      -                                   -                                   7.4              -

 Income (loss) from operations, non-GAAP                                 5.8                                 4.7                                 14.9             (1.7)

 Net loss, GAAP                                                          (9.3)                               (2.7)                               (33.7)           (23.8)

 Stock-based compensation                                                13.9                                6.9                                 38.7             19.5

Note: Figures have been rounded. Marketplace gross margin is using Marketplace revenue and total cost of revenue less Managed Services cost of revenue.
Managed Services gross margin is using Managed Services revenue and Managed Services cost of revenue.                                                                             29
GAAP to Non-GAAP                                                          $ and share counts in millions
Reconciliation (Cont.)                                                    Percentages and per share data as stated

                                                                          Q3 2021                             Q3 2020                             9 Months 2021   9 Months 2020
 Amortization of intangible assets                                       -                                   0.7                                 0.7              1.3

 Tides Foundation common stock warrant expense                           0.2                                 0.2                                 0.6              0.6

 Impairment expense                                                      -                                   -                                   7.4              -

 Net Income (loss), non-GAAP                                             4.8                                 5.0                                 13.6             (2.4)

 Weighted-average shares outstanding used in computing loss per share, GAAP

 Basic                                                                   127.9                               120.7                               126.7            117.1

 Basic loss per share, GAAP                                              $(0.07)                             $(0.02)                             $(0.27)          $(0.20)

 Weighted-average shares outstanding used in computing earnings (loss) per share, non-GAAP

 Basic                                                                   127.9                               120.7                               126.7            117.1

 Diluted 1                                                               134.3                               129.7                               134.5            117.1

 Basic earnings (loss) per share, non-GAAP                               $0.04                               $0.04                               $0.11            $(0.02)

 Diluted earnings (loss) per share, non-GAAP                             $0.04                               $0.04                               $0.10            $(0.02)

Note: Figures have been rounded. Marketplace gross margin is using Marketplace revenue and total cost of revenue less Managed Services cost of revenue.
Managed Services gross margin is using Managed Services revenue and Managed Services cost of revenue.                                                                             30
Guidance
                                                                  Q4 2021                       FY 2021
  Revenue                                                         $130 million - $132 million   $496 million - $498 million

  Adjusted EBITDA                                                 $(2) million - $(4) million   $18 million - $20 million

  Basic weighted-average shares
                                                                  128 million - 130 million     N/A
  outstanding

  Diluted weighted-average shares
                                                                  N/A                           134 million - 136 million
  outstanding

  Non-GAAP basic loss per share                                   $(0.03) - $(0.05)             N/A

  Non-GAAP diluted EPS                                            N/A                           $0.05 - $0.07

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                               31
Upwork
Team

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021
Proven management team with decades
of experience at Upwork and other marketplace
and technology companies
                     Hayden Brown                                    Jeff McCombs
                     President & CEO                                 CFO
                     9 years                                         1 year

                     Zoe Harte                                       Sam Bright
                     Chief People Officer                              Chief Product &
                     8 years                                         Experience Officer
Appendix

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021
Our Business
Model
  Marketplace

  Upwork Basic                                                    Freelancers          $                Tiered service fees ( 5% / 10% / 20% ) and other

                                                                  Clients              $                Payment fee, FX, and other

  Upwork Plus                                                     Freelancers          $                Service fees (5% / 10% / 20%) and other

                                                                  Clients              $                Monthly subscription, payment fee, and other

  Upwork Enterprise & Other Premium Offerings                      Freelancers          $                Flat service fee

                                                                  Clients              $                Service fees, annual subscription, and other

  Managed Services

  •   Upwork is responsible for the deliverable
                                                                  Clients              $                Markup on pay rate to freelancers
  •   Engage freelancers on behalf of the client
  •   Directly invoice the client
                                                                                Gross Accounting Treatment
                                                                                GSV = Revenue

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                            35
Illustrative Revenue
Recognition and
Margin Profile
  Marketplace                                                                    Client Spend                                           Revenue                                     Revenue Less COR

  Upwork Basic and Plus                                                          $100                                                   ~$121               75-80%                  ~$93

                                                              Compliance         $100                                                   ~$302               75-80%                  ~$233

  Upwork Enterprise

                                                              Standard           $100                                                   ~$152               75-80%                  ~$113

  Managed Services

                                                                                 $100                                                   $100                 ~19%                   ~$194

Notes: 1 Revenue does not include FX, payments, and freelancer subscription fees. 2 Illustrative rate assuming enterprise customer pays list price for enterprise compliance and standard. 3 Marketplace COR based on
2020 COR minus costs of freelancer services to deliver Managed Services as a percentage of 2020 Marketplace revenue. 4 Cost of freelancer services to deliver Managed Services based on 2020 cost of freelancer
services to deliver Managed Services as a percentage of 2020 Managed Services Revenue.

© 2021 Upwork Inc.      Q3’21 Investor Presentation   October 2021                                                                                                                                                      36
Key Metric                                                        Gross Services Volume (GSV)
Definitions                                                        Gross services volume, or GSV, includes both client spend and additional fees
                                                                  charged for other services.

                                                                  Active Client
                                                                  A client who has had spend activity during the trailing 12-month period is
                                                                  considered active.

                                                                  GSV per Active Client
                                                                  GSV per active client is calculated by dividing total trailing 12-month GSV by
                                                                  the number of active clients at the date of measurement.

© 2021 Upwork Inc.   Q3’21 Investor Presentation   October 2021                                                                                    37
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