On November 18, 2025, Upwork Inc. (Nasdaq: UPWK), a leader in the human and AI-powered work marketplace, held its 2025 Investor Day, where it presented an ambitious long-term growth strategy aimed at capitalizing on the rapidly evolving landscape of flexible work. The event featured insights from President and CEO Hayden Brown, CFO Erica Gessert, and other key executives, who articulated how Upwork has transformed its operations over the past three years to better harness the potential of artificial intelligence (AI).

2. Transforming the Business Model

Leveraging AI for Growth

Underlining the theme of innovation, CEO Hayden Brown emphasized that Upwork has executed a "complete reinvention" of its business model. The company is now entering what he describes as "Upwork’s most exciting chapter yet," supported by a new, AI-native platform tailored for businesses of all sizes. The initiative aims to capture a larger share of the estimated $1.3 trillion global digital knowledge work market, with a focus on three strategic growth drivers:

Transforming Human + AI Work: Upwork's AI strategy is anchored by the introduction of Uma™, an AI work agent designed to enhance workflows within the Upwork Marketplace. The company expects this strategy to yield over $100 million in incremental Gross Service Volume (GSV) in 2025 alone. AI-related work categories have already generated an annualized GSV of $300 million, boasting a remarkable growth rate of over 50% in Q3 2025.

Accelerating SMB Growth: Upwork's targeted product launch strategy aims to tap into the $530 billion small and medium-sized business (SMB) market. The premium offering, Business Plus, is designed to attract higher-spending SMB customers, thereby enhancing retention rates. The company plans to amplify this offering with ongoing marketing and product advancements in the coming years.

Unlocking Enterprise Expansion: The launch of Lifted, Upwork's new subsidiary, represents a bold foray into the $650 billion contingent labor market for enterprise clients. Lifted aims to provide a comprehensive, compliant solution for large organizations to source, contract, manage, and pay contingent talent, marking a significant evolution in Upwork's enterprise strategy.

3. Financial Outlook: Growth Projections

During the Investor Day, CFO Erica Gessert provided an optimistic financial outlook for the coming years:

2026 Projections

GSV Growth Rate: 4-6%

Revenue Growth Rate: 6-8%

Adjusted EBITDA Margin: Approximately 29%

2028 Projections

GSV CAGR: 7-9%

Revenue CAGR: 13-15%

Adjusted EBITDA CAGR: Approximately 20%

Gessert noted that these ambitious targets reflect both the results of Upwork’s business transformation and the structural advantages embedded in its model, particularly in the context of AI advancements.

4. Conclusion: A Future-Ready Organization

As Upwork moves forward, it positions itself as a pioneer in the evolving landscape of work, integrating advanced technologies to enhance its service offerings. With a clear growth strategy and strong financial targets, Upwork aims to solidify its leadership in the global marketplace, ensuring it remains at the forefront of the human and AI collaboration revolution.

The full presentation materials and a recorded video webcast of the Investor Day, including a Q&A session with Upwork executives, are available on the company’s Investor Relations website.

As Upwork Inc. embarks on this transformative journey, it not only seeks to redefine work for businesses of all sizes but also to create opportunities in every era of work, as it has done throughout its history.

Original press release