Leveraging AI 256 | How to build business strategy for the AI era, A detailed blueprint with Andrew Rabinovich, CTO and Head of AI + ML at Upwork
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Jan 6, 2026 
Join Andrew Rabinovich, CTO and Head of AI & ML at Upwork, as he explores the evolving landscape of work in the AI era. With a rich background in machine learning, he explains how AI can amplify freelancer productivity rather than replace it. Discover how Upwork is shifting from mere talent matching to delivering concrete outcomes. Andrew also reveals insights on AI agents like UMA, which can help translate vague ideas into actionable plans, and discusses the birth of new skills in the process of automation.
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Human-Centered AI Amplifies People
- Andrew Rabinovich frames AI as human-centered tools that amplify people rather than replace them.
- He highlights AI's role in expanding human abilities by automating routine tasks so people tackle higher-level work.
25 Years Of AI Experience Shapes View
- Andrew shares his 25 years in ML and AI across Google, Magic Leap, and startups before joining Upwork via acquisition.
- He uses that experience to argue for human-centered AI that augments rather than replaces talent.
Freelancers Want Repetitive Tasks Automated
- Freelancers on Upwork welcome automating repetitive, boring parts of their workflow to focus on creative work.
- Andrew describes two paths: freelancers build their own automation or use platform tools that embed automation systematically.