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Investor Day November 18, 2025
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Safe Harbor Statement This presentation and accompanying webcast of Upwork Inc. (together with its wholly owned subsidiaries, the “Company,” “we,” “us,” or “our”) contain "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, including financial outlook and future growth targets, information or predictions concerning the future of our business or strategy, market opportunity and market size, future products, features, or functionality, anticipated events and trends, potential growth or growth prospects, our competitive position, technological and market trends, industry environment, the economy, our plans with respect to share repurchases, the expected impact and timing of strategic initiatives, including the launch of Lifted, our enterprise-focused subsidiary, and its acquisitions of Bubty B.V. and Ascen Inc., and other future conditions. We have based these forward-looking statements largely on our current expectations and projections as of November 18, 2025 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, assumptions, 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 November 18, 2025, 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 September 30, 2025, filed with the SEC on November 4, 2025, 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. The information in this presentation on new products, features, and functionality is intended to outline our general product direction and should not be relied upon in making a purchasing or investment decision. The information on new products, features, and functionality is for informational purposes only and shall not be incorporated into any contract. The information on new products, features, and functionality is not a commitment, promise, or legal obligation to deliver any material, code or functionality. The development, release, and timing of any product, features or functionality described for our products remain at our sole discretion. Upwork, the Upwork logo, “Uma™, Upwork’s Mindful AI,” Lifted, 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. Non-GAAP Financial Measures 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 substitutes for the most directly comparable financial measures prepared in accordance with GAAP. In particular, (1) adjusted EBITDA excludes stock-based compensation expense, which has recently been, and will continue to be for the foreseeable future, a significant recurring expense for our business and an important part of our compensation strategy, (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) material acquisition-related deal costs. In addition, 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 Appendix to this presentation, and investors are encouraged to review the reconciliations and not rely on any single financial measure to evaluate our business. We have not reconciled our adjusted EBITDA targets to GAAP net income, adjusted EBITDA margin targets to GAAP profit margin, or free cash flow targets to GAAP cash provided by operating activities because certain items that impact GAAP net income, GAAP profit margin, and GAAP cash provided by operating activities are uncertain or out of our control and cannot be reasonably predicted. In particular, stock-based compensation expense is impacted by the future fair market value of our common stock and other factors, all of which are difficult to predict, subject to frequent change, or not within our control. The actual amount of these expenses during the periods presented will have a significant impact on our future GAAP financial results. Accordingly, a reconciliation of adjusted EBITDA targets to GAAP net income, adjusted EBITDA margin targets to GAAP profit margin, and free cash flow targets to GAAP cash provided by operating activities is not available without unreasonable effort.
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Today’s Agenda THE NEW UPWORK Hayden Brown, President & Chief Executive Officer ACCELERATING SMB GROWTH ON AN AI-POWERED MARKETPLACE Dave Bottoms, General Manager, Marketplace CUSTOMER PANEL Moderated by Peter Sanborn, VP, Strategy, Corporate Development & Partnerships BREAK UPWORK’S AI ADVANTAGE Andrew Rabinovich, Chief Technology Officer, Head of AI & ML UNLOCKING ENTERPRISE EXPANSION Ernesto Lamaina, General Manager, Lifted A FOUNDATION FOR ACCELERATING GROWTH Erica Gessert, Chief Financial Officer Q & A 3 | Investor Day 2025
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The new Upwork Hayden Brown President & Chief Executive Officer 44 | Investor Day 2025
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We are at a turning point for work. We’ve reinvented Upwork to lead the AI era of work. 5 | Investor Day 2025
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A new growth era for Upwork $202M +4% YoY $60M$1,018M +2% YoY Revenue Adjusted EBITDAGSV 30% adjusted EBITDA margin Q3 2025 Note: Adjusted EBITDA and adjusted EBITDA margin are non-GAAP financial measures. 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. GSV and Adjusted EBITDA are defined in the appendix of this presentation. 6 | Investor Day 2025
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The new Upwork Clear traction with three massive growth opportunities Fundamentally reinvented business for the next chapter Accelerating growth and exceptional profitability 7 | Investor Day 2025
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Headlines diverge AI is already taking white-collar jobs. Economists warn there’s ‘much more in the tank.’ “ Will AI improve or eliminate jobs? It depends on who you ask. “ AI is not yet replacing workers in the US, researchers find. “ 8 | Investor Day 2025
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9 | Investor Day 2025 INVESTOR DAY 2025 Net-new AI work Fractionalization of full-time jobs AI is a strong tailwind 9 | Investor Day 2025
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relies on New needs for writers and editors Upwork talent works alongside AI tools 10 | Investor Day 2025
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INVESTOR DAY 2025 AI driving business results +12% YoY project size +5% YoY GSV/active client +50% YoY AI clients Note: As of or for the three months ended September 30, 2025. 11 | Investor Day 2025
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Indicate adoption of AI tools will likely increase demand for fractional or flexible labor Source: Upwork B2B Workforce Marketplace Survey, based on responses from U.S.-based hiring decision-makers (October 2025). 77% 12 | Investor Day 2025
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13 | Investor Day 2025 The human and AI-powered work marketplace Proprietary work data Work delivery platform: AI-powered & end-to-end Category breadth: High spend & retention Business demand: SMB through enterprise clients Talent supply: Global & highly skilled talent pool
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14 | Investor Day 2025 Built for long-term relationships and complex work AI-native platform 70% of new job posts touched by Uma Work delivery platform
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15 | Investor Day 2025 ~800K high-quality active clients +7% YoY new client spend +11% YoY growth in new clients with >$1K spend in first quarter SMB and enterprise business demand Note: As of or for the three months ended September 30, 2025.
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16 | Investor Day 2025 18M active talent ~2M with advanced degrees 10K skills Global, skilled talent supply
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17 | Investor Day 2025 The human and AI-powered work marketplace Proprietary work data Work delivery platform: AI-powered & end-to-end Category breadth: High spend & retention Business demand: SMB through enterprise clients and agents Talent supply: Global & highly skilled talent pool and agents
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18 | Investor Day 2025 >130 categories ~40% of clients are multi-category Drives superior economics Category breadth Note: Multi-category clients for trailing four quarters ended September 30, 2025.
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19 | Investor Day 2025 10+ petabytes of data Growing daily Powering AI-enhanced work delivery Proprietary work data
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20 | Investor Day 2025 Pg. 20Pg. 20 20 | Investor Day 2025
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relies on Enables critical workforce agility Powers product and services growth 21 | Investor Day 2025
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relies on SMB client in marketplace Built extensive CX and fraud operations team on Upwork 22 | Investor Day 2025
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Upwork reinvented Product Marketplace built on AI-native platform Customers Tailored solutions for SMB and enterprise: Business Plus + Lifted Operations Smaller, more nimble and AI-powered team 23 | Investor Day 2025
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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 24 | Investor Day 2025 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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Unlocking Enterprise expansion Accelerating SMB growth Transforming human + AI workThree growth building blocks 1 2 3 25 | Investor Day 2025
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Transforming human + AI work Expanding AI-powered workflows Accelerating AI category growth Integrating AI agents 26 | Investor Day 2025 1
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Driving $100M increase in GSV in 2025 Uma™, Upwork’s Mindful AI Expanding AI-powered workflows 27 27 | Investor Day 2025 1
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Accelerating AI category growth $300M Annualized GSV from AI-related work Q3 rise in GSV from AI-related work +50% 28 | Investor Day 2025 1
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29 | Investor Day 2025 INVESTOR DAY 2025 Integrating AI agents AI Agents Human Experts Clients 1
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Accelerating SMB growth 30 | Investor Day 2025 2
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INVESTOR DAY 2025 Infrastructure + solutions that power enterprise contingent work programs Unlocking Enterprise expansion 31 | Investor Day 2025 3
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7- 9% CAGR 13 -15% CAGR ~20% CAGR GSV Revenue Adjusted EBITDA Targeting accelerating growth CAGR across GSV, revenue and adjusted EBITDA Our 3-year outlook 3232 | Investor Day 2025
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Amplifying AI tailwinds Driving SMB and enterprise growth Growing top and bottom line results The new Upwork 33 | Investor Day 2025
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INVESTOR DAY 2025 Accelerating SMB growth on an AI-powered marketplace Dave Bottoms General Manager, Marketplace 34 | Investor Day 2025
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World’s largest and highest-quality platform for flexible knowledge workers 10K skills 18M active professionals 250K AI experts 130+ categories Note: Largest as measured by GSV. 35 | Investor Day 2025
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Uma powers our AI-nativeMarketplace 36
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37 | Investor Day 2025 Uma helps clients post jobs and talent write proposals 37 37 | Investor Day 2025
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38 | Investor Day 2025 Uma assists with messaging and relevant work summaries 38 | Investor Day 2025
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Uma conducts candidate interviews and summarizes work delivery
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40 | Investor Day 2025 INVESTOR DAY 2025 Net-new AI work Fractionalization of full-time jobs AI is a strong tailwind 40 | Investor Day 2025
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Demand for net-new AI work is accelerating AI Apps & Integration AI & Machine Learning Digital Marketing Virtual AssistanceMobile Development E-commerce Data Extraction Data Mining & Management ERP / CRM Software Community Management Blockchain & Crypto 400 10 20 30 Quarters since category emerged Annual GSV 41 | Investor Day 2025
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AI is fractionalizing work and expanding demand for flexible expertise Traditional organizational structures Organizations seek fractional expertise to drive AI value Existing full-time roles augmented by fractional talent 42 | Investor Day 2025
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Accelerating SMB growth 43 | Investor Day 2025
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44 | Investor Day 2025 44 2028 global market size $530BSMBs are the backbone of the global economy 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). 44 | Investor Day 2025
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SMB is our most valuable segment Greater share of wallet Hire more for complex jobs More satisfied with Upwork 45 | Investor Day 2025
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“ Growing SMBs need tailored experiences We need to find quality talent quickly for complex projects. Access to top 1% talent “We need to hire a team and across multiple roles. Uma Recruiter “We need different people involved in hiring decisions. Team-based hiring “We need flexibility on payment options to better manage budgets. Net-30 payment terms 46 | Investor Day 2025
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47 | Investor Day 2025 Business Plus Instant access to top 1% talent on Upwork 47 | Investor Day 2025
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48 | Investor Day 2025 Uma-powered recruiter helps SMBs hire teams rapidly Business Plus 48 | Investor Day 2025
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Team-based features help SMBs collaborate on hiring Business Plus 49 | Investor Day 2025
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50 | Investor Day 2025 Net-30 terms give SMBs financial flexibility, boosting spend and retention Business Plus
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INVESTOR DAY 2025 Business Plus sees strong organic growth 36% QoQ active client growth 33% QoQ GSV growth 2.5x GSV per active client vs. Marketplace avg Note: As of or for the three months ended September 30, 2025. 51 | Investor Day 2025
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INVESTOR DAY 2025 INVESTOR DAY 2025 Activating demand for Business Plus
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53 | Investor Day 2025 Clear path to scale SMB growth 53 Now: 2025 - Q126 Introduce AI-native marketplace Complete AI-native end-to-end journey Strengthen Business Plus for growing AI categories Next: 2026 Develop new value-added services for SMBs Orchestrate full work delivery across Uma, agents, and talent Future: 2027+
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AI-native marketplace transformation drives GSV growth Capturing net-new AI demand and fractionalized work adoption Business Plus powering SMBs’ growth and AI transformation 54 | Investor Day 2025 Accelerating SMB growth on an AI-powered marketplace
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55 | Investor Day 2025 INVESTOR DAY 2025 Customer panel 55 | Investor Day 2025
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Hearing directly from our customers Gabe Richman Founder & CEO Peter Sanborn VP, Strategy, Corporate Development & Partnerships Cory Hymel VP, Product and Research Moderator Phil Rasori COO 56 | Investor Day 2025
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57 | Investor Day 2025 INVESTOR DAY 2025 Upwork’s AIadvantage Andrew Rabinovich CTO, Head of AI & Machine Learning 57 | Investor Day 2025
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A foundational layer behind the new Upwork 58 | Investor Day 2025
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59 | Investor Day 2025 State-of-the-art search and recommendation platform ~5% Higher conversionQuery understanding Retrieval Ranking Ads & monetization Literal keyword matching Keyword lookups Outsourced models Third-party algorithms In-house, multi-task deep learning models with conversational intent driving: ● Higher recall ● Personalization ● Faster surfacing of most relevant talent ● Dynamic ads for clients FROM TO RESULT ~20% for talent 59 | Investor Day 2025 Note: Conversion rate improvement year-to-date October 2025 compared to 2024.
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60 | Investor Day 2025 New tech layer for next-generation experiences >50% ~20%~70% <1 week Better content accuracy More proposals Less cost to compute to ship vs. 3 months HIGHER QUALITY LOWER COST BETTER EXPERIENCES FASTER THROUGHPUT High-Quality Platform Data Mixture of Experts & Knowledge Graph Custom Model Training & Evaluation Active Learning Loop 60 | Investor Day 2025 Note: Accuracy, cost and proposal count compared to GPT-4o baseline.
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61 | Investor Day 2025 The power of a closed loop ecosystem Proprietary work data Work delivery platform: AI-powered & end-to-end Category breadth: High spend & retention Business demand: SMB through enterprise clients and agents Talent supply: Global & highly skilled talent pool and agents
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62 | Investor Day 2025 Recognized by: We have 10+ petabytes of real- world work data 62 | Investor Day 2025
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63 | Investor Day 2025 INVESTOR DAY 2025 The first human + AI agent marketplace AI Agents Human Experts Clients
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64 | Investor Day 2025 Flexible talent lead AI agent adoption Independent professionals on Upwork Full-time employees 78% 53% Source: Upwork Future Workforce Index (April 2025). Denotes percentage using AI tools multiple times a week. ~1.5x more likely to use AI tools
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65 | Investor Day 2025 Clients want AI-enabled human talent Human-in-the-loop (assisted use) Human-on-the-loop (supervised autonomy) Human-out-of-the-loop (full autonomy) Not comfortable 5% 3% >90% prefer human involvement 38% >90% prefer human involvement Human-in-the-loop (assisted use) Humans remain in control and make the final decisions. Human-on-the-loop (supervised autonomy) Humans review and approve outputs before they are finalized. Human-out-of-the-loop (full autonomy) Al performs tasks and makes decisions without human involvement. Not comfortable 5% 3% 54% 38% Source: Upwork B2B Workforce Marketplace Survey, based on responses from U.S.-based hiring decision-makers (October 2025). Shows percentage of decision makers’ preference for human involvement with AI models. 54% >90% prefer human involvement
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66 | Investor Day 2025 66 >90% prefer human involvement Human-in-the-loop (assisted use) Humans remain in control and make the final decisions. Human-on-the-loop (supervised autonomy) Humans review and approve outputs before they are finalized. Human-out-of-the-loop (full autonomy) Al performs tasks and makes decisions without human involvement. Not comfortable 5% 3% 54% 38% CAGR 2028 AI agent global market size $120B >50% A fast-growing, natural market extension for Upwork 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). CAGR 2025 through 2028. 66 | Investor Day 2025
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67 | Investor Day 2025 Clear path to integrating agents 67 Now: 2025 - Q126 Continue to evolve Uma – greater personalization, deeper insight Innovate agent collaboration space and proprietary benchmark (HAPI) Roll out agents to the marketplace, tested and validated through HAPI benchmark Next: 2026 Orchestrate full work delivery across Uma, agents, and talent Future: 2027+
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68 | Investor Day 2025 Upwork’s agent collaboration space Testing environment where freelancers, and third-party agents collaborate to deliver work outcomes Quality Speed Human experts Agents Playground Human experts + agents
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69 | Investor Day 2025 Rapid integration into full marketplace next year Upwork’s agent collaboration space
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70 | Investor Day 2025 Our new evaluation system to verify agents The Human + Agent Productivity Index : HAPI Recognized by… The Human + Agent Productivity Index: HAPI
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71 | Investor Day 2025 Early results validate the future of work is human + AI HAPI: Upwork’s Human + Agent Productivity Index Number of attempts AI only 19.9% 39.8% 19.6% 32.3% 51.2% 33.5% 41.0% 55.9% 42.3% 1st human turn 2nd human turn Completion rate on selected low-complexity tasks human only Claude Sonnet 4 Gemini 2.5 Pro OpenAI GPT 5 Predicted Observed up to~70% improvement Recognized by…
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72 | Investor Day 2025 Uma becoming an orchestrator of work delivery between agents and talent Capabilities Functions Client Candidate evaluation General Q&A Dialogue > Outcome plan Proposal generation Match / discovery / recommendation Project plan Project management and evaluation Agent orchestration Outcome Delivery Talent Agents LLM-as-a-judge Mixture-of-judges Evaluate Short term (prompt) Long term (RAG) Orchestrate Reason & act Chain of thought Qualify
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74 | Investor Day 2025 INVESTOR DAY 2025 New channels, unmatched feedback and trusted human input The new Upwork unlocks value for all AI Agents Human Experts Clients More throughput, more demand, higher-value work, and new revenue streams Amplified productivity and earnings potential Faster, higher-quality outcomes grounded in trust
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State-of-the-art search and rec and next-generation AI infrastructure Strong moat from our closed loop, data-rich ecosystem Clear path to unlock value for agents, talent and clients 75 | Investor Day 2025 Upwork’s AI advantage
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INVESTOR DAY 2025 Unlocking Enterprise expansion Ernesto Lamaina General Manager, Lifted 76 | Investor Day 2025
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One solution built for enterprise companies to source, contract, manage and pay contingent talent. 77 | Investor Day 2025 ,
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78 | Investor Day 2025 78 >90% prefer human involvement Human-in-the-loop (assisted use) Humans remain in control and make the final decisions. Human-on-the-loop (supervised autonomy) Humans review and approve outputs before they are finalized. Human-out-of-the-loop (full autonomy) Al performs tasks and makes decisions without human involvement. Not comfortable 5% 3% 54% 38% 2028 global market size $650BEnterprise contingent labor is massive Access to talent Flexibility Efficiency 78 | Investor Day 2025 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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AI is a major tailwind AI is pushing functional leaders to leverage contingent more than FTEs; all our expected headcount growth is happening in contingent. Source: Upwork B2B Workforce Marketplace Survey, based on responses from U.S.-based hiring decision-makers (October 2025). Companies that expect increased demand for fractional labor to support adoption of AI tools CWP Program Leader, Global Financial Institution “ 77% 79 | Investor Day 2025
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How enterprises access contingent labor 80 | Investor Day 2025 Established workflows, policies and compliance requirements Engage through 5 contract types Engagement types Staff augmentation Employer of record Outcomes Agent of record Independent contractor
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Trusted by 300+ enterprise companies 81 | Investor Day 2025
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Why clients have been working with us High-quality talent network Fast delivery Enterprise grade 82 | Investor Day 2025
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High-quality talent network Total value of share repurchase since 2024: 18M Active professionals 10K Skills 4.92/5 Average rating Our partnership has been transformative, providing us access to a global talent pool that boosts our productivity and creativity while ensuring cost-efficiency and flexibility for our team. Director of Strategy & Business Development, Large Multinational Industrial Company “ 83 | Investor Day 2025 Note: Talent pool and skills represent access to the Upwork Marketplace.
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Fast delivery Made hiring this talent seamless and incredibly fast – they were up and running in less than 48 hours. Director of Creative, Multinational Conglomerate of Prestigious Beauty Brands “As fast as same day To receive shortlist 3 days To fill As fast as 30 minutes To redeploy 84 | Investor Day 2025
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Enterprise grade To reach our goals, we need to move faster, better, and cheaper, with ironclad security and trust. I sleep well at night because I know it is all taken care of. VP of IT, Leading AI-Powered Identity Verification Platform “Global Compliant Platform & service 85 | Investor Day 2025
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86 | Investor Day 2025 Prior barriers to unlocking additional growth Enterprise ecosystem and workflows Engagement types Directly provided 2 types, dependent on partners Limitations in ability to deliver talent via existing workflows and distribution channels IC AOR EOR Staff Aug OutcomesContingent Talent Centralized Contingent Workforce Programs (CWP) Functional Leaders & Hiring managers
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87 | Investor Day 2025 Recent acquisitions filled gaps Enterprise ecosystem and workflows Engagement types Directly provide all contract types Able to deliver talent via existing workflows and distribution channels IC AOR EOR Staff Aug OutcomesContingent Talent Centralized Contingent Workforce Programs (CWP) Functional Leaders & Hiring managers
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88 | Investor Day 2025 Fast access to high-quality Upwork Marketplace talent Comprehensive solution for enterprise contingent needs Ability to meet clients where they are 88 | Investor Day 2025
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89 | Investor Day 2025 Access to fraction of annual spend 89 $950M+ IC / AOR spend $50M Large pharma company EOR / Staff Aug / Outsourcing spend Actual share of wallet: ~20% $1B+ Annual spend for contingent Spend available before launching Lifted
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90 | Investor Day 2025 90 $950M+ IC / AOR spend $50M Spend available after launching Lifted Large pharma company EOR / Staff Aug / Outsourcing spend Remains fully available Becomes available + possible to increase share of wallet Full contingent spend access with Lifted $1B+ Annual spend for contingent
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$50M-1B+ Contingent labor budgets per year / per company ICP Thousands of employees & billions in revenue SPEND Focus on 5,000 companies in our Ideal Customer Profile 91 | Investor Day 2025
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Expand share of wallet within existing contract types Expand share of wallet with existing clients Gain share of wallet in new contract types Execution via existing account management and customer success management (CSM) structure 92 | Investor Day 202592 | Investor Day 2025
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Win net-new customers with 3-step approach Execution via agile marketing and sales team Pilot Adopt Expand 93 | Investor Day 2025
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Positive leading indicators Existing client Prospect Leveraging us for one contract type FROM Final stages of RFP for 3 contract types TO Large services company Large financial network “Impossible to work together as you do not offer the contract types we need” FROM Inviting us to next RFP TO 3x GSV $10M+ GSV 94 | Investor Day 2025
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Why Lifted? We unlock an estimated 10-30% cost savings We unify and elevate the ecosystem We provide high-quality talent, fast 95 | Investor Day 2025
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96 | Investor Day 2025 Clear path to expand in Enterprise 96 Now: 2025 - H126 Drive expansion conversations and land discovery Expand with existing customers Land pilots with new customers Next: H2 2026 Scale Future: 2027+
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Significantly expanded available market with launch of Lifted Early positive indicators from both existing clients and prospects Target growth in H2’26 and scale in FY27 97 Unlocking Enterprise expansion 97 | Investor Day 2025
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INVESTOR DAY 2025 A foundation for accelerating growth Erica Gessert Chief Financial Officer 98 | Investor Day 2025
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Confident growth outlook Foundation of durable profitability Strong balance sheet to accelerate growth 99 | Investor Day 2025 Delivering profitable growth
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100 | Investor Day 2025 The human and AI-powered work marketplace Proprietary work data Work delivery platform: AI-powered & end-to-end Category breadth: High spend & retention Business demand: SMB through enterprise clients and agents Talent supply: Global & highly skilled talent pool and agents
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101 | Investor Day 2025 The human and AI-powered work marketplace Proprietary work data Work delivery platform: 70% of new job posts touched by Uma Category breadth: 50 categories with over $10M GSV Business demand: ~800K active clients Talent supply: 18M active professionals Note: Category spend for trailing four quarters ended September 30, 2025. Active clients as of September 30, 2025.
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INVESTOR DAY 2025 A platform built to deliver high-value, recurring work 85%+ of GSV comes from retained clients Note: As of or for the three months ended September 30, 2025. High value work defined as greater than $1,000. $5K+ GSV per active client 90% of GSV comes from high-value work 102 | Investor Day 2025
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INVESTOR DAY 2025 Attracting and retaining a higher quality customer base +11% new clients spend >$1K in their first quarter 170bps YoY improvement to churn 6x higher GSV from retained clients 103 | Investor Day 2025 Note: As of or for the three months ended September 30, 2025.
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INVESTOR DAY 2025 Building the new Upwork Strategic acquisitions AI-driven job post generator AI recruiter AI interviews AI proposal writer Conversational search AI work experience summaries Freelancer Plus Business Plus Platform development 104 | Investor Day 2025
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Outperforming the market Note: Average revenue CAGRs for fiscal years 2022 - 2025E for overall staffing industry and online marketplace peers. Staffing industry +8% -4% Online marketplaces 0% 105 | Investor Day 2025
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Source: The Bureau of Labor Statistics - Job Opening and Labor Turnover Survey (JOLTS). Seasonally adjusted, total nonfarm job openings through August 1, 2025. Untethered from the macro environment rolling 3-month GSV Job openings 106 | Investor Day 2025 2018 2019 2021 2022 2023 2024 20252020
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Poised for accelerating GSV growth +16% +1% -3% 0% 2022 2023 2024 2025 2026 2027 2028 YoY 107 | Investor Day 2025 Q3’25 +2%
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Traction in three large markets 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 108 | Investor Day 2025 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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Unlocking Enterprise expansion Accelerating SMB growth Transforming human + AI workThree growth building blocks 1 2 3 109 | Investor Day 2025
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$100M incremental GSV in 2025 driven by AI platform optimization Transforming human + AI work YoY growth in searches for talent with agentic experience Growing 50%+ YoY $300M Estimated GSV run rate year end 2025 ~12x AI category AI agentsAI-powered workflows 110 | Investor Day 2025 1 Note: Growth in searches for the three months ended September 30, 2025.
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2.5x Business Plus GSV per active client vs. Marketplace in Q3 20+bps take rate contribution in Q3 Accelerating SMB growth 33% QoQ GSV growth rate in Q3 5%+ Target Marketplace GSV from Business Plus in 2026 111 | Investor Day 2025 2
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FY26 Lifted GSV growth target Unlocking Enterprise expansion 10x Target contract size 25% 300+ enterprise companies 112 | Investor Day 2025 3
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The building blocks for GSV growth are clear SMB growth Human + AI work Enterprise expansion Ads and pricing 7-9% CAGR FY 2028Target FY 2025 113 | Investor Day 2025
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114 | Investor Day 2025 Monetization momentum built on proven growth engines Connects & ads products Subscriptions Variable freelancer fee Value added services for SMBs 24% YoY growth in Freelancer Plus subscription revenue Early experimentation for 2025 and deeper platform testing and application in 2026. 18% YoY growth in connects & ads revenue 2027 Value-added services for SMBs 24% YoY Freelancer Plus revenue growth in Q3 Early experimentation in 2025 18% YoY revenue growth in Q3
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Substantial room to grow take rate SMB growthHuman + AI work Enterprise expansion Ads and pricing FY2028Target FY2025 Take Rate Average Industry Take Rate Note: Average industry take rate based on 2025 reports by public online work marketplace companies. ~23% 30%+ 115 | Investor Day 2025
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Accelerated revenue growth from GSV growth and take rate expansion SMB growth Human + AI work Enterprise expansion Ads and pricing FY2028Target Total FY2025 Take rate expansion contribution GSV contribution 13 -15% CAGR 116 | Investor Day 2025
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INVESTOR DAY 2025 We’ve built a foundation of profitable and scalable growth Adjusted EBITDA ($M) Adjusted EBITDA Margin $73 $168 $223 2022 2023 2024 2025E Note: 2025 represents midpoint of full year 2025 guidance. Adjusted EBITDA and adjusted EBITDA margin are non-GAAP financial measures. 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. 11% 22% 28% -$4 -1% 117 | Investor Day 2025
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INVESTOR DAY 2025 35% 20% Reduced sales costs by Reduced enterprise cost to serve by 40% Reduced enterprise customer acquisition cost by Sales Lower cost to acquire and serve Since 2022, we’ve… 118 | Investor Day 2025 Note: Sales costs and cost to serve 2025E compared to fiscal year 2022. Customer acquisition cost fiscal year 2024 compared to fiscal year 2022.
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INVESTOR DAY 2025 55% 24% Reduced marketing spend by Increased GSV yield from marketing by 113% Increased marketing-led GSV/contract by Marketing Lower cost with higher yield Since 2022, we’ve… 119 | Investor Day 2025 Note: Nine months ended September 30, 2025 compared to nine months ended September 30, 2022.
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INVESTOR DAY 2025 Note: AI-assisted code on a monthly basis. Reduction in cost ten months ended October 31, 2025 compared to fiscal year 2022. Code production speed year-over-year for trailing four quarters ended September 30, 2025; speed based on meaningful lines of code accepted and merged per engineer. R&D Higher productivity and throughput 120 | Investor Day 2025 25-35% 32% AI-assisted code reduction in cost per line of code 16% faster code production
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Efficient cash conversion fueling growth and flexibility Pg. 121 Note: 2025 represents midpoint of full year 2025 guidance. Adjusted EBITDA, adjusted EBITDA margin, free cash flow, and free cash flow conversion rate are non-GAAP financial measures. An explanation of non-GAAP financial measures and reconciliations to their most directly comparable GAAP financial measures can be found in the appendix of this presentation. Adjusted EBITDA ($M) Adjusted EBITDA Margin Free Cash Flow ($M) 85% Adjusted EBITDA to FCF conversion 2023-2025E $73 $168 $223 2022 2023 2024 2025E 11% 22% 28% -$4 -1% $39 $139 $216 $3 121 | Investor Day 2025
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INVESTOR DAY 2025 Capital deployment focused on shareholder value Total value of share repurchase since 2024 Focused organic investment Adjusted EBITDA margin target of 35% by 2029 Targeted M&A Continue record of high-ROI M&A Capital return Offset stock-based compensation and opportunistic additional share repurchases 122 | Investor Day 2025 Note: Repurchases through October 2025.
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123 | Investor Day 2025 123 4-6% GSV growth rate target Accelerating our growth in 2026 6-8% Revenue growth rate target ~29% Adjusted EBITDA margin target *Absorbing 2pp dilution from Lifted growth investment 123 | Investor Day 2025
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7- 9% CAGR 13 -15% CAGR ~20% CAGR GSV Revenue Adjusted EBITDA Targeting accelerating growth CAGR across GSV, revenue and adjusted EBITDA Our 3-year outlook 124124 | Investor Day 2025
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The new Upwork Accelerating growth and exceptional profitability 2025-2028: 7-9% GSV, 13-15% revenue, ~20% adjusted EBITDA growth CAGRs Rebuilt platform, customer focus and operations Growing traction in massive markets +50% YoY GSV growth in $300M+ AI work; projected GSV growth: 100% YoY in Business Plus and 25% YoY in Lifted 125 | Investor Day 2025 Note: AI category GSV on an annualized basis. Fundamentally reinvented business for the next chapter
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Q&A 126 | Investor Day 2025
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The new Upwork 127 | Investor Day 2025
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Pg. 128 Appendix and definitions 128 | Investor Day 2025
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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. 129 | Investor Day 2025
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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 and is the primary driver of our business. Marketplace Take Rate Take Rate We define take rate as total revenue divided by total GSV. Key definitions 130 | Investor Day 2025
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GAAP to non-GAAP reconciliation 131 | Investor Day 2025 (1) For the year ended December 30, 2023, we recognized a gain on early extinguishment of debt of $38.9 million, which is included in other income (expense), net in the consolidated statement of operations and comprehensive income (loss). (2) For the year ended December 31, 2024, we recognized a non-cash tax benefit of $140.3 million from the release of a valuation allowance on certain deferred tax assets. (3) For the twelve months ended December 30, 2025, 2024, 2023 and 2022, we incurred $0.8 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. For the three months ended September 30, 2025, we incurred $0.2 million of expense related to the Tides Foundation warrant. (4) During the three months ended September 30, 2025, we incurred $1.9 million acquisition-related costs in connection with our business combinations of Ascen Inc. and Bubty B.V. (5) For the year ended December 31, 2024, we incurred $19.2 million in costs related to the execution of our restructuring plan announced in October 2024. Of this amount, $18.4 million is included in Other, while the remaining amount is allocated between stock-based compensation expense and Other income, net. (6) For the year ended December 31, 2022, in response to Russia’s invasion of Ukraine, we incurred certain incremental expenses associated with our humanitarian response efforts. These expenses are not representative of our ongoing operations, and, as a result, we excluded these costs from adjusted EBITDA for the twelve months ended December 31, 2022. Represents (i) $1.4 million of special one-time bonuses to our team members in the region impacted by Russia’s invasion of Ukraine, (ii) $1.5 million of expenses incurred in connection with the relocation of our team members in the impacted region, (iii) $1.1 million of donations made to humanitarian aid organizations to support initiatives related to humanitarian response efforts in the impacted region, primarily to Direct Relief International, a humanitarian aid organization, and (iv) $0.4 million of payments of one-time service award bonuses (and associated taxes) to certain of our team members paid in recognition of contributions made by such team members to our humanitarian response efforts in the impacted region. Reconciliation of GAAP Net Income (Loss) to adjusted EBITDA (In thousands) (Unaudited) Three Months Ended Twelve Months Ended December 31, 30-Sep-25 2024 2023 2022 Net income (loss) $ 29,335 $ 215,586 $ 46,887 $ (89,885) Add back (deduct): Stock-based compensation expense 19,789 68,391 74,195 75,501 Depreciation and amortization 7,946 14,813 9,449 8,057 Other income, net (1) (5,917) (25,221) (60,137) (3,275) Income tax (benefit) provision (2) 6,340 (125,159) 1,990 536 Other (3)(4)(5)(6) 2,134 19,183 750 5,037 Adjusted EBITDA $ 59,627 $ 167,593 $ 73,134 $ (4,029) Profit margin 15% 28% 7% -15% Adjusted EBITDA margin 30% 22% 11% -1%
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132 | Investor Day 2025 Twelve Months Ended December 31, 2024 2023 2022 Cash provided by operating activities $ 153,563 $ 52,708 $ 11,497 Less: purchases of property, plant & equipment and cash outflows from internally developed software (14,444) (13,351) (8,733) Free cash flow $ 139,119 $ 39,357 $ 2,764 Reconciliation of Cash Provided by Operating Activities to Free Cash Flow (In thousands) (Unaudited) GAAP to non-GAAP reconciliation