Slide 1: Upwork Investor Presentation
NASDAQ: Upwork UPWK Investor Presentation August 2026 1
Slide 2: Safe Harbor Statement
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 o
Slide 3: The new Upwork
The new Upwork Fundamentally reinvented business for the next chapter Clear traction with three massive growth opportunities Strong profitability and free cash flow generation © 2026 Upwork Inc. Proprietary and confidential. Do not distribute. 3
Slide 4: The human and AI-powered work marketplace
The human and AI-powered work marketplace Work delivery platform: Business demand: AI-powered & end-to-end SMB through enterprise clients & AI agents Proprietary work data Category breadth: Talent supply: High spend & retention Global & highly skilled talent pool & AI agents © 2026 Upwork Inc. Propr
Slide 5: A $1.3T market opportunity in 2028
A $1.3T market opportunity in 2028 SMBs Enterprise Agentic AI $530B $650B $120B 2028 global spend on 2028 global spend on Agentic AI work aligned contingent digital knowledge contingent digital knowledge with or enhancing digital work in companies with <500 work in companies with >500 knowledge work
Slide 6: Three growth pillars
1 Transforming human + AI work Three growth 2 Accelerating SMB growth pillars 3 Unlocking Enterprise expansion © 2026 Upwork Inc. Proprietary and confidential. Do not distribute. 6
Slide 7: Second Quarter Results
Second Q2’26 Quarter Results GSV Revenue GAAP Gross Margin $966.4M $191.7M 76.4% -3.6% year-over-year -2% year-over-year -135bps year-over-year Adjusted EBITDA Free Cash Flow Take Rate $64.1M $35.9M 19.8% 33.4% adj. EBITDA margin 56.1% FCF/adj. EBITDA +40 bps year-over-year “GSV,” “Adjusted EBITDA,”
Slide 8: Green shoots that validate our strategy
Green shoots that validate our strategy 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. Strong SMB traction with Business Plus GSV per active client
Slide 9: Transforming human + AI work
Transforming human + AI work GSV from AI-related work ~$330 million on an annualized basis in Q2 2026 22%+ >50% Year-over-year GSV growth in Year-over-year GSV growth in Total AI Category Work AI Strategy & Consulting Year-over-year growth rates compare the second quarter of 2026 to the second quart
Slide 10: Uniquely positioned to offer human-supervised agents at scale
Uniquely positioned to Clients offer human-supervised agents at scale AI Human Agents Experts © 2026 Upwork Inc. Proprietary and confidential. Do not distribute. 10
Slide 11: Accelerating SMB Growth
Accelerating Business Plus GSV SMB Growth Plan ~$64M Attract and convert more new SMB customers with tailored solutions, such as Business Plus, and value added services to unlock the SMB market opportunity Q2 2026 highlights: • Business Plus GSV increased 24% quarter-over-quarter and 174% year-over-
Slide 12: Upwork has a key role to play as the AI diffusion layer for SMBs
Upwork has a key role to play as the AI diffusion layer for SMBs Diffusion SMBs are helping AI Capabilities AI Adoption drive ~$330M in The application layer annual GSV on opportunity Upwork for AI-related work and skills Upwork is uniquely positioned to Our human- provide the critical talent SMBs sup
Slide 13: Strategic focus on high-value client acquisition driving GSV per Active Client
Strategic focus on GSV per Active Client ($K) high-value client acquisition driving GSV per Active Client and new expansion amid acquisition environment pressures Y/Y GSV per Active Client. © 2026 Upwork Inc. Proprietary and confidential. Do not distribute. 13
Slide 14: Appendix + Definitions
Appendix + Definitions 14
Slide 15: See Key Definitions section in this earnings presentation.
(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. 15
Slide 16: Condensed Consolidated Balance Sheets
UPWORK INC. CONDENSED CONSOLIDATED BALANCE SHEETS (in thousands) (Unaudited) December 31, June 30, 2026 2025 ASSETS Current assets Cash and cash equivalents $ $ 294,356 Marketable securities 378,425 Funds held in escrow, including funds in transit 180,752 ‘Trade and client receivables, net 76,236 Pr
Slide 17: Condensed Consolidated Statements of Operations
CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS Revenue Marketplace Enterprise Total revenue Cost of revenue Gross profit Operating expenses Research and development Sales and marketing General and administrative Provision for transaction losses Total operating expenses Income from operations Other
Slide 18: Condensed Consolidated Statements of Cash Flows
UPWORK INC. CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (in thousands) (Unaudited) ‘Three Months Ended June 30, ‘2026 2025 CASH FLOWS FROM OPERATING ACTIVITIES: Net income $ 25,404 $ 32,726 ‘Adjustments to reconcile net income to net cash provided by operating activities: Provision for transacti
Slide 19: Consolidated Statements of Cash Flows
UPWORK INC. CONSOLIDATED STATEMENTS OF CASH FLOWS (In thousands) (Unaudited) The following table reconciles cash, cash equivalents, and restricted cash as reported in the condensed consolidated balance sheets to the total of the same amounts shown in the condensed consolidated statements of cash flo
Slide 20: Reconciliation of Cash Provided by Operating Activities to Free Cash Flow
UPWORK INC. RECONCILIATION OF CASH PROVIDED BY OPERATING ACTIVITIES TO FREE CASH FLOW (In thousands) (Unaudited) Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 Cash provided by operating activities $ 46.874 $ 72,514 $ 69,893 $ 109,479 Less: purchases of property, plant & e
Slide 21: During the three and six months ended June 30, 2026, we incurred $13.8 million
(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 inco
Slide 22: Non-GAAP Financial Measures
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, adjus
Slide 23: Key Definitions
Key Definitions Active Clients Enterprise Revenue We define an active client as a client that has had spend activity on any Upwork We define Enterprise revenue as revenue from our Enterprise offerings, which platform or other workforce solution during the 12 months preceding the date of primarily consis
Slide 24: Key Definitions
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 ca
Slide 25: About Upwork
About Upwork About Upwork Contact: Upwork Inc.’s (Nasdaq: UPWK) family of companies connects investor@upwork.com 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