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August 2021 © 2021 Upwork Inc. Q2’21 Investor Presentation Upwork Q2 Investor Presentation August 16, 2021

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Page 1: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Upwork Q2 Investor PresentationAugust 16, 2021

Page 2: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 2

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 June 30, 2021 filed with the Securities and Exchange Commission (the "SEC") on July 29, 2021 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 U.S. 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 U.S. 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 U.S. GAAP financial measures set forth in the Appendix, and not rely on any single financial measure to evaluate the Company's business.

Safe Harbor

Page 3: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 3

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 shareholder letter. 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, other non-cash transactions. For the three and six months ended June 30, 2021, other non-cash transactions included an impairment charge of $7.4 million.

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 shareholder letter and investors are encouraged to review the reconciliation.

Page 4: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation© 2021 Upwork Inc. Proprietary and confidential. Do not distribute. July, 2021Q2’21 Investor Presentation

Our Mission

Create economic opportunities so people have better lives.

© 2021 Upwork Inc. Proprietary and confidential. Do not distribute.August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Page 5: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation© 2021 Upwork Inc. Proprietary and confidential. Do not distribute. July, 2021Q2’21 Investor Presentation

Our Vision

Independent talent at the heart of every business.

© 2021 Upwork Inc. Proprietary and confidential. Do not distribute.August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Page 6: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Uniquely Positioned to Succeed

Massive TAM with secular tailwinds

Deep and expanding competitive moats

Proven and experienced management team

Multiple growth opportunities

Largest work marketplace at scale

1

6

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

Page 7: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

~225 Million

Estimated number of global remote knowledge workers

1

Upwork Opportunity

$1.3T

7

Creating a Massive and Growing Opportunity

~$5,850

Average freelancer GSV 2

x =

1 2021 estimate from Gartner - Forecast Analysis: Remote Workers Forecast, Worldwide August 2020.2 TTM as of Dec. 31, 2020.

Page 8: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Upwork Is the Most Comprehensive Work Marketplace

8

Direct Contracts

Payroll

Talent Marketplace TM

Bring Your Own Talent

Project Catalog TM

Talent Scout TM

...What’s Next?

Enterprise Suite

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

Page 9: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

~50% of Fortune 500 companies are clients 2

Featuring the Most Robust Community of Clients and Freelancers

~40% of clients hired in multiple categories 2

73% of talent have college degrees 1

50+ categories with $10M+ in GSV 2

10,000+ skills

1 February 2021 Upwork internally conducted survey.2 Based on the trailing 12-month period ending March 31, 2021.

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Page 10: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Freelancer Stages of Adoption

10

Cus

tom

er V

alue

Freelancer Adoption Over Time

4

3

2

Freelancer-First

Companies change view from “why Upwork?” to “why not Upwork?”

Companies make investments to leverage freelancers as core to the way they get work done

Freelancers complement FTEs and become an option for additional projects

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

1Project

Hybrid

Scaling

Page 11: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Our Goal: 100% of businesses will have freelancers on their teams in the future

11

Page 12: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Brand Awareness

Acquisition / Retention

Generating Abundant Growth Opportunities

Enterprise

Product Line Diversification

Share of Wallet

Long TermMid TermNear Term

Opportunistic M&A

Expected horizon for significant value creation

Internationalization and Localization

Talent Services

Product Integrations

Take Rate Expansion

12

Page 13: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Local Staffing Cos

Regional Staffing Cos

Platform-first service model Traditional staffing service model

The Race to Win the $1.3T Work Marketplace Opportunity

13

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

Talent pool

Vetting & talent management

Match & reputation

Platform & payments

SalesShortlisting & success management

B2Bmarketing

Payroll

Hybrid service model

Work Marketplace

Page 14: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Freelancer Basic

Freelancer Plus

Agency Plus

• Access to quality projects

• Quickly apply and get hired

• Get paid securely and on time

Includes all Freelancer Basic features +

• Customized profile URL

• Insight into competitorbid ranges

• Monthly Connects package* *not included in Agency Plus

Includes all Freelancer Plus features +

• Unlimited team members

• Shared Connects functionality

14

Three Talent Plans

Page 15: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Basic Plus Enterprise:Standard

Enterprise:Compliance

• Access to a globaltalent pool

• Safe and easy payments

• Payment protection plan

• Customer support

Includes all Basic features +

• Invites to talent

• Featured Jobs upgrade

• Connects package

• Recruiting services

Includes all Plus features +

• Custom reporting

• API access

• Expert-vetted talent poolsand talent clouds

• SSO / permissions

• Purchase order management

• Consolidated invoicing and billing

Includes all Enterprise: Standard features +

• Compliance services

• Worker classification

• Misclassification indemnification

• Work protection program

15

Four Client Plans

Page 16: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Find work quicklyAccess to quality, flexible projects from our global network

Get paid on timeReceive security and peace of mind with Upwork Payment Protection

Build reputationEstablish long-term credibility and relationships with roster of clients

Growth opportunitiesInsights on in-demand skills and emerging areas

FlexibilityExpanding number of ways to Upwork

Value for Freelancers

Quality talentGlobal access to a verified Virtual Talent Bench™ across categories and price points

Fast access to talentReceive proposals within minutes; 3 days average time to contract

Cost-effective projectsTake hiring budgets further with average 50% savings vs. hiring locally

Work efficiently, effectivelyEnd-to-end suite of workflow tools

FlexibilityExpanding number of ways to Upwork

Value for Clients

Creating a Virtuous Cycle

This engine results in:Highly sticky double opt-in platform with long-term relationships and recurring use, leading to increasing scale and recurring revenue

Value for Upwork

Cross-selling

More freelancers

More skills / categories

More clients

Increased GSV

More / bigger projects

16

Page 17: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 17

Infinite Personas and Categories

• Build and maintain my website

• Build and maintain my mobile app

• Do QA testing on my product

• Augment or replace my internal UI / UX team

• Maintain a safe and secure dev environment for me

• ...

• Augment my design staff

• Translate my marketing assets

• Build my new landing page

• Develop my campaign strategy

• Develop my social media strategy

• Execute my social media strategy

• ...

• Recruit and manage my customer support operations

• Recruit and manage a skilled tech support team

• Let me outsource my accounting to a trusted accountant

• Provide me project-based accounting support

• ...

Tech & Product LeadExample: VP, Engineering

Marketing & Creative LeadExample: VP, Marketing

Operations LeadExample: COO

Growth through breadth

Gro

wth

thro

ugh

dept

h∞

Page 18: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

1 2 3 4Launched our work marketplace marketing efforts to build awareness and drive demand

Expanding paid acquisition reach by:

Improving conversion rates by:

Automating and scaling SEM and social through proprietary bidding tool:

Key Marketing and Acquisition Growth Levers for 2021 and Beyond

• Expanding SEM keywords and mobile SEM conversion optimizations

• Growing international presence +40% YoY via keyword expansion globally

• Shifting to new brand messaging across channels to improve CTRs

18

• Matching intent to best product lines

• Improving CLTV model to optimize client keyword bidding

• Increasing registration-to-Start conversions through better client onboarding

• Aggressively supporting Enterprise Sales land and expand efforts

• Optimizing reactivation and retention efforts by moving to more holistic marketing automation

Page 19: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

The Enterprise Opportunity

19

1,600

8K

200+

Target ideal customer profile (ICP) accounts

Target ICP customers with spend currently in the Marketplace

Current Enterprise clients

250+ employee US-based companies assigned to sales teams (both inbound and outbound)51K

1,000 accounts could deliver $1-2B in GSV

+ Many more globally

© 2021 Upwork Inc. Q2’21 Investor Presentation August 2021

Page 20: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 20

Focus Area Initiatives Achievements to Date

Environment • Reducing emissions by limiting our physical corporateoffice footprint through our remote-first working model

• Reducing unnecessary commuting and travel• Purchasing carbon offsets that promote environmental

sustainability

✓ Enabled team members to avoid over 1 million commuting miles in 2019✓ Achieved carbon neutrality for 2019 and 2020✓ Committed to remaining carbon neutral going forward

Social • Building a more robust diversity, inclusion and belonging(DIBs) infrastructure

• Leveraging data to inform strategic talent process decisions• Preparing quantitative disclosures to demonstrate our progress on

DIBs-related initiatives

✓ 50% of Board is female✓ 3 of our 8 directors are from underrepresented communities

1

Governance • Evolving Board and governance practices to reflect our maturation as a public company

• Focusing on and responding to stockholder feedback• Acting to protect and grow long-term stockholder value

✓ Implemented majority-vote standard for director elections and adopted proxy access

✓ The Board’s Nominating and Governance Committee oversees all ESG functions

Commitmentto StrongESG Practices

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

Page 21: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Innovating the work marketplace1

21

Our Winning Strategy

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

Page 22: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Financial Highlights

Page 23: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

2019

$7.4

2020 Q2’21

$14.0

-$1.2

$7.3

Q2’20

$301

$374

Upwork at a Glance

Client Spend Retention

114%Active Clients

725kGSV per Active Client

$4,198

As of June 30, 2021

162kCore Clients

Gross Services Volume (GSV) ($M)

$2,087

2019 2020 Q2’20 Q2’21

$2,524

$582

$876

50%↑21%↑

Revenue ($M)

$301

2019 2020 Q2’20 Q2’21

$374

$88

$124

42%↑24%↑

Adjusted EBITDA ($M)

714%↑89%↑

Note: Adjusted EBITDA is a non-GAAP measure.

23

Page 24: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 24

TTM Active ClientsYoY Growth

Note: 1 See appendix for the definition of active clients.

0k 0%

5%

10%

15%

20%

25%

100k

200k

300k

400k

500k

600k

700k

Active client count growth hasaccelerated for 5 consecutive quarters

17%

12%

9%

7%

9%

10%10%10%

TTM

Act

ive

Clie

nts 1

YoY

Gro

wth

Q4-2019 Q2-2020 Q4-2020Q3-2020Q1-2020Q2-2019Q1-2019 Q3-2019 Q1-2021

30%

Q2-2021

27%

25%

Strong Active Client Growth

24

Page 25: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

GSV PerActive ClientIs Increasing

$3,000 0%

5%

15%

10%

$3,250

$4,000

$3,500

$3,750

GS

V 1

YoY

Gro

wth

14%

12%

10%

9% 9%

6%

4%3%

YoY GrowthTTM Avg GSV / Active Client(1)

8%

2%

Note: 1 See appendix for the definition of GSV per active client.

Q4-2019 Q2-2020 Q4-2020Q3-2020Q1-2020Q2-2019Q1-2019 Q3-2019 Q1-2021 Q2-2021

Page 26: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

% of Revenue FY2018 FY2019 FY2020 YTD2021 LT Target

Marketplace Gross Margin

175% 77% 78% 78% 80-85%

Managed Services Gross Margin

2

17% 17% 19% 20% 20%

Total Gross Margin

68% 71% 72% 73% 80-85%

R&D 21% 19% 20% 20% 15-20%

S&M 28% 31% 34% 35% 20-25%

G&A 16% 18% 15% 14% 8-10%

Transaction Losses

2% 1% 1% 1% 1-2%

Adjusted EBITDA 1% 2% 4% 6% 30-35%

26

Our Compelling Margin Structure• High and expanding gross margins

• Industry-leading investment levels in R&Dto extend competitive moats

• Opportunities for leverage in R&D and G&A

• Will invest aggressively in sales and marketingto drive growth and maximize economicvalue added

Notes: 1 Marketplace gross margin is defined as total gross profit, excluding revenue from Managed Services and cost of freelancer services to deliver Managed Services, divided by Marketplace revenue.

2 Managed Services gross margin is defined as Managed Services revenue less cost of freelancer services to deliver Managed Services, divided by Managed Services revenue.

Numbers are non-GAAP. Non-GAAP here excludes SBC, amortization, and non-cash charitable donations. All numbers reflect depreciation expense, except for Adjusted EBITDA.

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Page 27: Upwork Q2 Investor Presentation

$ and share counts in millionsPercentages and per share data as stated

Q2 2021 Q2 2020 6M 2021 6M 2020

GAAP Net Loss (16.5) (11.0) (24.4) (21.0)

Stock-based compensation expense 13.5 7.1 24.8 12.7

Depreciation and amortization 2.6 2.5 5.7 4.8

Interest expense 0.1 0.3 0.3 0.5

Other (income) expense, net - (0.3) (0.1) 0.5

Income tax provision - - - -

Tides Foundation common stock warrant expense 0.2 0.2 0.4 0.4

Impairment expense 7.4 - 7.4 -

Non-GAAP Adjusted EBITDA 7.3 (1.2) 14.2 (2.2)

Marketplace cost of revenue, GAAP 25.3 18.1 48.5 34.7

Stock-based compensation (0.2) (0.2) (0.4) (0.4)

Marketplace cost of revenue, non-GAAP 25.1 17.9 48.1 34.3

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

2727

GAAP to Non-GAAP Reconciliation

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.

Page 28: Upwork Q2 Investor Presentation

$ and share counts in millionsPercentages and per share data as stated

Q2 2021 Q2 2020 6M 2021 6M 2020

Managed Services cost of revenue, GAAP 7.8 7.3 15.0 14.2

Managed Services cost of revenue, Non-GAAP 7.8 7.3 15.0 14.2

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

Cost of revenue, GAAP 33.1 25.4 63.5 48.9

Stock-based compensation (0.2) (0.2) (0.4) (0.4)

Total cost of revenue, non-GAAP 32.9 25.2 63.1 48.5

Total gross margin, non-GAAP (%) 26% 29% 27% 28%

Research and development, GAAP 28.1 20.5 54.7 39.9

Stock-based compensation (4.0) (2.8) (7.3) (4.7)

Research and development, non-GAAP 24.1 17.8 47.5 35.2

Sales and marketing, GAAP 45.8 34.4 85.4 65.1

Stock-based compensation (1.6) (1.3) (2.9) (2.2)

Sales and Marketing, non-GAAP 44.2 33.1 82.5 62.9

2828

GAAP to Non-GAAP Reconciliation (Cont.)

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.

Page 29: Upwork Q2 Investor Presentation

$ and share counts in millionsPercentages and per share data as stated

Q2 2021 Q2 2020 6M 2021 6M 2020

General and administrative, GAAP 32.4 17.1 55.9 34.9

Stock-based compensation (7.8) (2.9) (14.2) (5.3)

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

Tides Foundation common stock warrant expense (0.2) (0.2) (0.4) (0.4)

Impairment expense (7.4) - (7.4) -

General and administrative, non-GAAP 17.0 13.4 33.3 27.9

Loss from operations, GAAP (16.4) (11.0) (24.1) (20.0)

Stock-based compensation 13.5 7.1 24.8 12.7

Amortization of intangible assets - 0.7 0.7 1.3

Tides Foundation common stock warrant expense 0.2 0.2 0.4 0.4

Impairment expense 7.4 - 7.4 -

Income (loss) from operations, non-GAAP 4.7 (3.0) 9.1 (5.7)

Net loss, GAAP (16.5) (11.0) (24.4) (21.0)

Stock-based compensation 13.5 7.1 24.8 12.7

2929

GAAP to Non-GAAP Reconciliation (Cont.)

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.

Page 30: Upwork Q2 Investor Presentation

$ and share counts in millionsPercentages and per share data as stated

Q2 2021 Q2 2020 6M 2021 6M 2020

Amortization of intangible assets - 0.7 0.7 1.3

Tides Foundation common stock warrant expense 0.2 0.2 0.4 0.4

Impairment expense 7.4 - 7.4 -

Net Income (loss), non-GAAP 4.6 (3.0) 8.8 (6.7)

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

Basic 126.7 116.5 126.0 115.3

Basic loss per share, GAAP $(0.13) $(0.09) $(0.19) $(0.18)

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

Basic 126.7 116.5 126.0 115.3

Diluted 1 134.0 - 134.2 -

Basic loss per share, GAAP $(0.13) $(0.09) $(0.19) $(0.18)

Diluted income per share, non-GAAP 1 $0.03 - $0.07 -

3030

GAAP to Non-GAAP Reconciliation (Cont.)

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. 1 Not applicable when in a net loss position.

Page 31: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 31

Q3 2021 FY 2021

Revenue $125 million - $127million $490 million - $494 million

Adjusted EBITDA $4 million - $5 million $16 million - $20 million

Diluted Weighted-Average Shares Outstanding

134 million - 136 million 133 million - 137 million

Non-GAAP Diluted EPS $0.01 - $0.03 per diluted share $0.05 - $0.07 per diluted share

Guidance

Page 32: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Upwork Team

Page 33: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 33

Proven management team with decades of experience at Upwork and other marketplace and technology companies

Saty BahadurChief Technology Officer<1 year

Hayden BrownPresident & CEO9 years

Sam BrightChief Product & Experience Officer<1 year

Eric GilpinSenior Vice PresidentSales5 years

Brian LeveyChief Business Affairs& Legal Officer8 years

Zoe HarteChief People Officer8 years

Jeff McCombsCFO<1 year

Page 34: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Appendix

Page 35: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

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• Engage freelancers on behalf of the client• Directly invoice the client

35

Our Business Model

Clients Markup on pay rate to freelancers

Gross Accounting TreatmentGSV = Revenue

$

$

$

$

$

$

$

Page 36: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation 36

Illustrative Revenue Recognition and Margin Profile

Marketplace Client Spend Revenue Revenue Less COR

Upwork Basic and Plus $100 ~$121 ~$9

3

Upwork Enterprise

Compliance $100 ~$30

2 ~$23

3

Standard $100 ~$15

2 ~$113

Managed Services

$100 $100 ~$19

4

75-80%

75-80%

75-80%

~19%

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.

Page 37: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Metric Timing

Client spend retention Deprecating after Q2-2021

Core clients Deprecating after Q2-2021

TTM active clients Quarterly disclosure starting Q2-2021

TTM GSV per active client Quarterly disclosure starting Q2-2021

Summary of Changes to Our Publicly Disclosed Metrics

37August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Page 38: Upwork Q2 Investor Presentation

August 2021© 2021 Upwork Inc. Q2’21 Investor Presentation

Key Metric Definitions

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Active Client

Gross Services Volume (GSV)

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

Gross services volume, or GSV, includes both client spend and additional fees charged for other services.

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.

Core Clients

A core client is defined as a client that has spent in the aggregate at least $5,000 since beginning to use our platform and also had spend activity during the 12 months preceding the date of measurement.

Client spend retention is calculated by dividing our recurring client spend by our base client spend. We define base client spend as the aggregate client spend from all clients during the four quarters ended one year prior to the date of measurement. We define our recurring client spend as the aggregate client spend during the four quarters ended on the date of measurement from the same clients included in our measure of base client spend.

Client Spend Retention