Bloomberg Businessweek Upwork Rolls Into the Human + AI Era
Nov 25, 2025
In this engaging discussion, Erica Gessert, CFO of Upwork, shares insights into the company's ambitious growth plans and AI investments. She reveals how Upwork is transforming the flexible work landscape by rebuilding its business model. Erica highlights three key areas of focus: AI innovation, small business expansion, and enterprise strategies. She explains how AI tools streamline hiring processes and improve job matching, while addressing current market trends and client demand. Discover how Upwork aims to capitalize on the $1.3 trillion digital knowledge work market!
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Rebuilding To Capture AI-Driven Growth
- Upwork repositioned itself by reinvesting in AI, SMBs, and enterprise to drive growth ahead of schedule.
- AI has become a material growth engine with $300M annualized GSV and accelerating adoption.
AI Removes Friction In Hiring
- Upwork uses AI to remove hiring friction by writing job posts and proposals and by recruiting automatically.
- Their UMA AI recruiter searches 18 million freelancers and yields higher fill rates than humans.
Automate Repetitive Hiring Tasks
- Use AI to automate repetitive hiring tasks like writing postings and proposals to speed matches.
- Leverage platform data so AI can surface better candidate fits faster than manual searches.