Slide 1: Upwork Investor Presentation
NASDAQ: Upwork UPWK Investor Presentation May 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 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 Proprietary work data Category breadth: Talent supply: High spend & retention Global & highly skilled talent pool 4 | Investor Day 2025
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 with contingent digital knowledge contingent digital knowledge 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
Slide 7: First Quarter Q1'26 Results
First Quarter Q1’26 Results GSV Revenue GAAP Gross Margin $987.1M $195.5M 77.2% Approximately flat year-over-year +1% year-over-year -114 bps year-over-year Adjusted EBITDA Free Cash Flow Take Rate $57.4M $12.9M 19.8% 29.4% adj. EBITDA margin 22.5% FCF/adj. EBITDA +29 bps year-over-year “GSV,” “Adjus
Slide 8: Green shoots that validate our strategy
Green shoots that validate our strategy AI opportunities Strong growth in AI work category within the Marketplace, up 40%+ year-over-year Beta version of human-supervised agent solution launched in Q2 ChatGPT Upwork app driving new activity, signaling a new AI demand channel Strong SMB traction with
Slide 9: Transforming human + AI work
Transforming human + AI work Data Updated Design, pls polish GSV from AI-related work exceeded $300 million on an annualized basis in Q1 2026 40%+ 37% ~50% Year-over-year GSV growth in Year-over-year GSV growth in Total AI Category Work AI Integration & Automation Year-over-year growth rates compare
Slide 10: Uniquely positioned to offer human-supervised agents at scale
Uniquely Clients positioned to offer human-supervised agents at scale AI Human Agents Experts 10 INVESTOR DAY 2025
Slide 11: Accelerating SMB Growth
Accelerating SMB Growth Business Plus GSV Attract and convert more new SMB Plan ~$52M customers with tailored solutions, such as Business Plus, and value added services to unlock the SMB market opportunity Q1 2026 highlights: • Business Plus GSV increased 34% quarter over quarter in Q1 2026 • Busine
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 SMBs are helping Diffusion drive >$300M in AI capabilities AI adoption annual GSV on Upwork for AI-related The application layer opportunity work and skills Our human- Upwork is uniquely positioned to supervised agent provide the critica
Slide 13: Enterprise interest in Lifted is growing
Enterprise interest in Lifted is growing 9x increase in opportunities with 3x increase in opportunities with existing clients new clients 13
Slide 14: Strategic focus on high-value client acquisition driving GSV per Active Client
Strategic focus on high-value client acquisition driving GSV per Active Client and new expansion amid acquisition environment pressures GSV per Active Client ($K) 14
Slide 15: Appendix + Definitions
Appendix + Definitions 15
Slide 16: 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. 16
Slide 17: Condensed Consolidated Balance Sheets
UPWORK INC. CONDENSED CONSOLIDATED BALANCE SHEETS (in thousands) (Wnaudited) December 31, March 31, 2026 2025 ASSETS Current assets Cash and cash equivalents s Marketable securities Funds held in escrow, including funds in transit ‘Trade and client receivables, net Prepaid expenses and other current
Slide 18: Condensed Consolidated Statements of Operations
UPWORK INC. CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS Revenue Marketplace Enterprise Total revenue Cost of revenue Gross profit Operating expenses Research and development Salos and marketing General and administrative Provision for transaction lossos Total operating expenses Income from opera
Slide 19: Condensed Consolidated Statements of Cash Flows
UPWORK INC. CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (ln thousands) (Unaudited) CASH FLOWS FROM OPERATING ACTIVITIES: Net income ‘Adjustments to reconcile net income to net cash provided by operating activities: Provision for transaction losses Depreciation and amortization Amortization of de
Slide 20: 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 21: 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 March 31, 2026 2025 Cash provided by operating activities $ 23,019 $ 36,965 Less: purchases of property, plant & equipment and cash outflows from internally developed s
Slide 22: Reconciliation of GAAP to Non-GAAP Results
UPWORK INC. RECONCILIATION OF GAAP TO NON-GAAP RESULTS (In thousands, except for percentages and share data) (Unaudited) Three Months Ended March 31, 2026 2025 Net income $ 31461 $ 37,730 Add back (deduct): Stock-based compensation expense 15,421 12,272 Depreciation and amortization 9,099 4,861 Othe
Slide 23: Non-GAAP Financial Measures
Non-GAAP Financial Measures To supplement our 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
Slide 24: 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 25: 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 26: 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 on-demand work type including freelance, agency, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which co