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Upwork Investor Presentation August 2026 NASDAQ : UPWK upwork
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2 Safe Harbor Statement This presentation of Upwork Inc. (together with its wholly owned subsidiaries, the “Company,” “we,” “us,” or “our”) contains "forward-looking" statements within the meaning of the federal securities laws. Forward-looking statements include all statements other than statements of historical fact, including any statements regarding our future operating results and financial position, information or predictions concerning the future of our business or strategy, future market opportunity and market size, future products, features, or functionality, anticipated events and trends, potential growth or growth prospects, competitive position, technological and market trends, industry environment, the economy, our plans with respect to share repurchases, the expected impact and timing of strategic or cost-saving initiatives, and other future conditions. We have based these forward-looking statements largely on our current expectations and projections as of the date hereof about future events and trends that we believe may affect our financial condition, results of operations, business strategy, short- and long-term business operations and objectives, and financial needs. 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 our control, and you should not place undue reliance on such forward-looking statements. Moreover, we operate in a very competitive and rapidly changing environment, and new risks emerge from time to time. We make no representation that the plans, intentions, expectations, or results disclosed in these forward-looking statements will be achieved or that future events and circumstances will occur, and actual results or events may differ materially and adversely from our expectations. The forward-looking statements are made as of the date hereof, and we do not undertake, and expressly disclaim, any obligation to update or revise any forward-looking statements, conform these statements to actual results, or make changes in our expectations, except as required by law. Additional information regarding the risks and uncertainties that could cause actual results to differ materially from our expectations is included under the caption "Risk Factors" in our Quarterly Report on Form 10-Q for the three months ended March 31, 2026, filed with the SEC on May 7, 2026, and in our other SEC filings, which are available on our Investor Relations website at investors.upwork.com and on the SEC’s website at www.sec.gov. Additional information will also be set forth under the caption “Risk Factors” in our Quarterly Report on Form 10-Q for the three months ended June 30, 2026, when filed. Undue reliance should not be placed on the forward-looking statements in this presentation. Neither we 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. Upwork, the Upwork logo, Lifted, UmaTM, and other registered or common law trade names, trademarks, or service marks of Upwork appearing in this presentation are the property of Upwork. This presentation may also contain additional trade names, trademarks, and service marks of other companies, including names, logos, and brands. All third-party trademarks are property of their respective owners, and any references to third-party trademarks are for identification purposes only and shall be considered nominative fair use under trademark law.
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3© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Clear traction with three massive growth opportunities The new Upwork Strong profitability and free cash flow generation Fundamentally reinvented business for the next chapter
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4© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. The human and AI-powered work marketplace Work delivery platform: AI-powered & end-to-end Category breadth: High spend & retention Business demand: SMB through enterprise clients & AI agents Talent supply: Global & highly skilled talent pool & AI agents Proprietary work data
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5© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. A $1.3T market opportunity in 2028 SMBs Agentic AI $120B Enterprise $650B$530B 2028 global spend on contingent digital knowledge work in companies with <500 employees 2028 global spend on contingent digital knowledge work in companies with >500 employees 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).
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6© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Three growth pillars Transforming human + AI work1 Accelerating SMB growth2 Unlocking Enterprise expansion3
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7© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Second QuarterResults Take RateFree Cash Flow $64.1M $35.9M 19.8% Adjusted EBITDA 33.4% adj. EBITDA margin +40 bps year-over-year56.1% FCF/adj. EBITDA Q2’26 GSV Revenue GAAP Gross Margin $966.4M $191.7M 76.4% -3.6% year-over-year -2% 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 second quarter 2026 results, please refer to our press release dated August 10, 2026, and our Quarterly Report on Form 10-Q for the three months ended June 30, 2026, when filed. -135bps year-over-year
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8© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Green shoots that validate our strategy Growing Enterprise interest Lifted’s country and contract-agnostic value prop steadily gaining interest and exposure. Lifted migrated its first wave of enterprise customers onto its new platform at the end of June, and expanded the go-to-market team, including hiring a new head of sales. Strong SMB traction with Business Plus GSV per active client reached another record of $5,230—up 5% year-over-year—the 8th quarter of sequential growth. Business Plus 2.5x year-over-year revenue growth in Q2 as larger SMBs utilize Upwork for complex, recurring needs. AI opportunities Launched our Model Context Protocol (MCP), connecting AI tools to the Upwork marketplace. Customers can connect to it through Claude, ChatGPT, Cursor, and any MCP-compatible product.
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9© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. GSV from AI-related work ~$330 million on an annualized basis in Q2 2026 Transforming human + AI work Year-over-year growth rates compare the second quarter of 2026 to the second quarter of 2025. Annualized GSV is GSV in the quarter multiplied by four. Year-over-year GSV growth in AI Strategy & Consulting >50%22%+ Year-over-year GSV growth in Total AI Category Work
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10© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Uniquely positioned to offer human-supervised agents at scale AI Agents Human Experts Clients
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11© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Accelerating SMB GrowthQ2 2026 highlights: • Business Plus GSV increased 24% quarter-over-quarter and 174% year-over-year • Business Plus active clients increased 16% quarter-over-quarter and 219% year-over-year • 38% of active clients on Business Plus in Q2 2026 had their first Upwork spend on Business Plus Attract and convert more new SMB customers with tailored solutions, such as Business Plus, and value added services to unlock the SMB market opportunity 2025-Q1 2025-Q2 2025-Q3 2025-Q4 2026-Q1 2026-Q2 ~$64M Business Plus GSV Plan
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12© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Upwork has a key role to play as the AI diffusion layer for SMBs AI Capabilities AI Adoption Diffusion The application layer opportunity Upwork is uniquely positioned to provide the critical talent SMBs need to take advantage of AI SMBs are helping drive ~$330M in annual GSV on Upwork for AI-related work and skills Our human- supervised agent product, launched in August 2026, goes even further in directly helping SMBs close this AI adoption gap Image from Sequoia AI Ascent keynote, 2026. Annual GSV represents annualized Q2 2026 GSV from AI-related work.
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13© 2026 Upwork Inc. Proprietary and confidential. Do not distribute. Strategic focus on high-value client acquisition driving GSV per Active Client and new expansion amid acquisition environment pressures GSV per Active Client ($K) Y/Y GSV per Active Client.
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14 Appendix + Definitions
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15 (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.
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21 (1) During the three and six months ended June 30, 2026, we incurred $13.8 million in costs related to the execution of the restructuring announced in May 2026. Of this amount, $12.8 million is included in Other, while the remaining amount is allocated between stock-based compensation and Other income, net. (2) For each of the three months ended June 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 six months ended June 30, 2026 and 2025, we incurred $0.4 million of such expense. (3) During the three and six months ended June 30, 2025, we incurred acquisition-related costs of $2.5 million in connection with our business combinations. These costs primarily consist of legal, accounting, and other professional fees, and are recorded in general and administrative expenses in the condensed consolidated statements of operations.
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22 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
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23 Key Definitions 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. Gross Services Volume (GSV) 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. 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. Connects Virtual tokens that are required for talent to bid on projects and purchase ads products on the Upwork Marketplace.
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24 Marketplace take rate measures the correlation between Marketplace revenue and Marketplace GSV and is calculated by dividing Marketplace revenue by Marketplace GSV. Marketplace Revenue Marketplace revenue represents the revenue derived from the Upwork Marketplace, including all offerings other than our Enterprise offerings. Marketplace Take Rate Take Rate We define take rate as total revenue divided by total GSV. Key Definitions
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25 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. About Upwork Contact: investor@upwork.com 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.