Q3' 26 Upwork Investor Presentation

Upwork Investor Presentation

NASDAQ:

UPWK

November 2026

The new Upwork

Fundamentally reinvented business for the next chapter

Clear traction with three massive growth opportunities

Strong profitability and free cash flow generation

The human and AI-powered work marketplace

Work delivery platform:

AI-powered & end-to-end

Business demand:

SMB through enterprise clients & AI agents

Proprietary work data

Category breadth:

High spend & retention

Talent supply:

Global & highly skilled talent pool & AI agents

A $1.3T market opportunity in 2028

SMBs

2028 global spend on contingent digital knowledge work in companies with <500 employees

Enterprise

2028 global spend on contingent digital knowledge work in companies with >500 employees

Agentic AI

Agentic AI work aligned with or enhancing digital knowledge work by 2028

Source: Upwork Market Study, a commissioned third-party study that estimates the flexible digital knowledge work market based on data from, among other sources, the Bureau of Labor Statistics, World Bank, and the International Labour Organization (October 2025).

1. Transforming human + AI work

2. Accelerating SMB growth

3. Unlocking Enterprise expansion

GSV Revenue GAAP Gross Margin

$914.1M $185.6M 76.1%

-10% year-over-year -8% year-over-year -115 bps year-over-year

Adjusted EBITDA

Free Cash Flow

Take Rate

$63.8M $53.9M 20.3%

34.4% adj. EBITDA margin

84.4% FCF/adj. EBITDA

+46 bps year-over-year

"GSV," "Adjusted EBITDA," "Free Cash Flow," and "Take Rate" are defined in the definitions section of this presentation. Adjusted EBITDA, adjusted EBITDA margin, free cash flow, and free cash flow conversion rate are non-GAAP financial measures and are presented for supplemental purposes only and should not be considered in isolation or as a substitute for financial information presented in accordance with GAAP. An explanation of non-GAAP financial measures and reconciliations to their most directly comparable GAAP financial measures can be found in the appendix of this presentation. For more information regarding our third quarter 2026 results, please refer to our press release dated November 2, 2026, and our Quarterly Report on Form 10-Q for the three months ended September 30, 2026, when filed.

Strategic growth pillars update

AI frontiers

The Upwork Model Context Protocol (MCP) server has seen rapid growth in adoption and usage among clients and freelancers. Weekly active users have increased 20x since the launch in August, while AI agents have made nearly 50 million requests.

MCP server usage is driving an estimated $3M in annualized Connects revenue.

Strong SMB traction with Business Plus

Q3 2026 GSV from Business Plus offering for SMBs increased 16% quarter-over-quarter and 132% year-over-year. Q3 2026 Business Plus active clients grew 9% quarter-over-quarter and 154% year-over-year.

40% of active clients on Business Plus in Q3 2026 had their first Upwork spend on Business Plus.

Doubling down on the Enterprise opportunity

Lifted acquired WorkMotion, a leading Employer of Record (EOR), enabling direct employment of contingent talent in 30+ countries. We continue to make strong progress on the migration of Enterprise customers to the Lifted platform.

human + AI work

GSV from freelancers with AI skills

~$450 million on an annualized basis in Q3 2026

Year-over-year growth in GSV from Talent with AI Skills

Year-over-year growth rates compare the third quarter of 2026 to the third quarter of 2025. Annualized GSV is GSV in the quarter multiplied by four.

Uniquely positioned to offer human-supervised agents at scale

AI

Agents

Clients

Human Experts

SMB Growth

Attract and convert more new SMB customers with tailored solutions, such as Business Plus, and value added services to unlock the SMB market opportunity

Q3 2026 highlights:

• Business Plus GSV increased 13%

  quarter-over-quarter and 132% year-over-year

• Business Plus represented 8% of Upwork's total GSV in Q3 2026

Business Plus GSV

~$72M

2025-Q2 2025-Q3 2025-Q4 2026-Q1 2026-Q2 2026-Q3

Upwork Now on-demand hiring built for the AI era

Strategic focus on high-value client acquisition driving GSV per Active Client and new expansion amid acquisition environment pressures

GSV per Active Client ($K)

Y/Y GSV per Active Client.

Appendix

+ Definitions

(1) See Key Definitions section in this earnings presentation.

(2) An explanation of non-GAAP financial measures and reconciliations to their most directly comparable GAAP financial measures can be found in the "Non-GAAP Financial Measures" section of this presentation.

AS SETS

Gurrenl asseis

UP'VORK IR C.

CONDENSED CONSOLIDATED BALAS CE 5HEET 8

5ept20 er 30, •' . .her3i,

s

UPWORK INC.

CONDENSED CONSOLIDATED STATEMENT S OF OPERATIONS

{In thousands, except for per share data) (Unaudited)

Revenue

Three Months Ended Nine Months Ended September 3D, September 3D,

2026 2025 2026 2025

CONDEN SED CON SDLIDATED STATEMENT S OF CASH FLOWS

C.4SH FLOWS FROM OPERATIN G ACTIVITIES:

Net inEome

Adjusbnenls to reconcile net income to net cash provided by operating zrctivities: Provision for Iransaclion losses

Degieciation and azriortizatior+ Amortization of debt issuance costs

Accrelion of disEounl on purchases of marketable securities. net Amortization of operating lease asset

Tides Foundation common stoch •/zzant expense Stock-based compensation expense

Deferred laxes

Losg on disposal of fixed assets

Changes in operaling assets and liabilities:

Toad e end client receivables Prepaid expenses and other assets Operating lense liability

Accounts payable

Accrued expe nses and oth er liabilities Deferred revenue

Net cash provided by operating acti'7ifies C.4SH FLOWS FROM INVESTING ACTIVITIES:

Purchases of marketable securities

Proceeds from matuñties ofmarkelable securities Proceeds from sale of marketable securities Purchase of equit'y inveslmenl

ñcquisili on of business, net of cash acquired

? 31,81 0 ? 29,335 ? 80, 675 ? 99, 791

876 2,113 4,995 5,707

11,353 7,946 29,23£ 1B,686

409 460 1,330 1,381

(238) {2,1951 (3,017 (5,699

444 179 1,280 564

188 1B8 'i63• 563

9,173 19,789 36,717 40,038

1,5SS {2,463) 3,19D (399

't1,352'I '{2,014"I {2,741 't1,654 5,827 3,378 192 40

{697'i '2081 ''1,255 600

2,311 4,571 1,466 (504

4,244 13,866 [27,820 16,777

44 134 855 667

65,947 75,079 135.840 184.558

- 1O6,791"i - '365,939 61,890 70,314 302.111 302.725

- 64 1,986 3,601

(2501 - {250 i

- '39, 436"i - '59,846'i

C.ASH, CASH EQUIVALENTS, .AND RESTRICTED CAS nd of qeriod ñ 396.392 ñ 476. 011 E 396.392 E 476.011

UPWORK INC.

CONSOLIDATED STATEMENTS OF CASH FLOWS

(In thousands)

(Unaudited)

The following tame reconEiies cash, cash equivalents, and restnEled cash as reported in the condensed consolidaled balance sheets to the tdal of the same amounis shoxzn in the condensed consolidated slalements of cash fIovrs as of the following (in thousands):

Cash and cash equivdents Restricted cash

Funds held in escrow, including funds in transit

September 30, December 31,

2026 20M

S 227,986 S 294,356 88OO 3,8OO

164,606 180,752

Tdal cash cash equivalenls and restricted cash as shown in the S 396,392 5 4T8,8O8

condensed consolidated sta&ment dEaWta•s

UPWORK INC.

RECONCILIATION OF CASH PROVIDED BY OPERATING ACTIVITIE 5 TO FREE CASH FLOW

(in thousands) Unaudited}

Threo Ionths Ended Nine Months Ended

September 30, September 30,

2026 2025 2026 2025

and cash outflows from intemaily developed

(1) For the three and nine months ended September 30, 2026, we incurred $4.3 million and $18.1 million in costs related to the restructuring announced in May 2026, respectively. Of these amounts, $2.7 million and $15.6 million, respectively, are included in Other, while the remaining amounts are allocated among "Stock-based compensation expense", "Depreciation and amortization", and "Other income, net".

(2) For each of the three months ended September 30, 2026 and 2025, we incurred $0.2 million of expense related to the warrant to purchase 500,000 shares of our common stock at an exercise price of $0.01 per share issued to the Tides Foundation in 2018, and for each of the nine months ended September 30, 2026 and 2025, we incurred $0.6 million of such expense.

(3) For each of the three and nine months ended September 30, 2026, we incurred transaction-related costs of $5.7 million in connection with WorkMotion Software GmbH acquisition. These costs primarily consisted of legal, accounting, and other professional fees, and were recorded in general and administrative expenses in the condensed consolidated statements of operations.

(4) For the three and nine months ended September 30, 2025, we incurred acquisition-related costs of $1.9 million and $4.4 million, respectively, in connection with our business combinations. These costs primarily consisted of legal, accounting, and other professional fees, and were recorded in general and administrative expenses in the condensed consolidated statements of operations.

To supplement our condensed consolidated financial statements, which are prepared in accordance with accounting principles generally accepted in the United States ("GAAP"), we present certain non-GAAP financial measures in this presentation, including adjusted EBITDA, adjusted EBITDA margin, free cash flow, and free cash flow conversion rate.

We use non-GAAP financial measures in conjunction with financial measures prepared in accordance with GAAP for planning purposes, including the preparation of our annual operating budget, as a measure of our core operating results and the effectiveness of our business strategy, and in evaluating our financial performance. These non-GAAP financial measures provide consistency and comparability with past financial performance, facilitate period-to-period comparisons of our 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 without regard to certain items that can vary substantially from company to company, and free cash flow allows investors to evaluate the cash generated from our underlying operations across periods.

Investors are cautioned that there are material limitations associated with the use of non-GAAP financial measures as analytical tools, and investors should not consider them in isolation or as a substitute for the most directly comparable financial measures prepared in accordance with GAAP. In particular, (1) adjusted EBITDA and certain of our other non-GAAP financial measures exclude stock-based compensation expense, which has recently been, and will continue to be for the foreseeable future, a significant recurring expense for our business and an important part of our compensation strategy, (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 and certain of our other non-GAAP financial measures do 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) material acquisition-related deal costs. In addition, the utility of free cash flow as a measure of our liquidity is limited as it does not represent the total increase or decrease in our cash balance for a given period. Moreover, the non-GAAP financial measures we use may be different from non-GAAP financial measures used by other companies, including companies in our industry, limiting their usefulness for comparison purposes. We compensate for these limitations by providing specific information regarding the GAAP items excluded from the non-GAAP financial measures that we present. Reconciliations of the non-GAAP financial measures presented in this presentation to their most directly comparable GAAP financial measures have been provided in the financial statement tables included in this presentation, and investors are encouraged to review the reconciliations and not rely on any single financial measure to evaluate our business.

Non-GAAP Financial Measures

Active Clients

We define an active client as a client that has had spend activity on any Upwork platform or other workforce solution during the 12 months preceding the date of measurement.

Adjusted EBITDA

We define adjusted EBITDA as net income adjusted for stock-based compensation expense; depreciation and amortization; other income (expense), net, which includes interest expense; income tax benefit (provision); and, if applicable, certain other gains, losses, benefits, or charges that are non-cash or are significant and the result of isolated events or transactions that have not occurred frequently in the past and are not expected to occur regularly in the future.

Connects

Virtual tokens that are required for talent to bid on projects and purchase ads products on the Upwork Marketplace.

Enterprise Revenue

We define Enterprise revenue as revenue from our Enterprise offerings, which primarily consist of Enterprise Solutions and Managed Services.

Free Cash Flow

We define free cash flow as cash provided by operations less purchases of property, plant and equipment and cash outflows from internally developed software.

Gross Services Volume (GSV)1

Gross services volume, or GSV, represents the total dollar value transacted through all Upwork platforms and other workforce solutions.

GSV per Active Client

GSV per active client is calculated by dividing total GSV during the

four quarters ended on the date of measurement by the number of active clients on the date of measurement.

1 GSV from freelancers with AI-skills for the three and twelve months ended September, 2026, reflects all GSV generated by freelancers whose profile lists at least one skill that overlaps with our internally maintained list of generative AI skills.

Key Definitions

Marketplace Revenue

Marketplace revenue represents the revenue derived from the Upwork Marketplace, including all offerings other than our Enterprise offerings.

Marketplace Take Rate

Marketplace take rate measures the correlation between Marketplace revenue and Marketplace GSV and is calculated by dividing Marketplace revenue by Marketplace GSV.

Take Rate

We define take rate as total revenue divided by total GSV.

Key Definitions

About Upwork

Upwork Inc.'s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent worker classification. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.

Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at upwork.com and follow on LinkedIn, Facebook,

Instagram, TikTok, and X; and learn more about Lifted at go-lifted.com and follow on LinkedIn.

Contact:

[email protected]

Disclosure Information

We use our Investor Relations website (investors.upwork.com), our Blog (upwork.com/blog), our X handle (twitter.com/Upwork), Hayden Brown's X handle (twitter.com/hydnbrwn) and LinkedIn profile (linkedin.com/in/haydenlbrown), and Erica Gessert's LinkedIn profile (linkedin.com/in/erica-gessert) as means of disseminating or providing notification of, among other things, news or announcements regarding our business or financial performance, investor events, press releases, and earnings releases, and as means of disclosing material nonpublic information and for complying with our disclosure obligations under Regulation FD.

About Upwork