Rearchitecting Upwork for the AI Era

About this session

Companies are investing billions of dollars in autonomous AI agents with the promise that software will soon complete professional work independently. But what actually happens when you test these systems on real jobs with real stakes?Andrew Rabinovich, Chief Technology Officer and Head of AI/ML at Upwork, brings a perspective shaped by 25 years in machine learning and one of the world’s largest real-world datasets on digital work. On the Upwork marketplace, more than 800,000 clients post over 3 million jobs each year across hundreds of professional categories, creating a live laboratory for testing the limits of AI agents in production environments. In this fireside chat, we’ll share insights from Upwork’s Human + Agent Productivity Index (HAPI), which evaluates how advanced AI agents perform on real paid tasks. The results reveal a consistent pattern: agents struggle to reliably complete even well-defined work on their own, but performance improves dramatically when paired with expert human guidance.Drawing on more than 10 petabytes of proprietary marketplace interaction data, this discussion will also focus on how Upwork rebuilt its platform for the AI era with Uma, an AI-native orchestration layer designed to coordinate human expertise and intelligent agents to deliver work outcomes faster and more reliably.Join this session to understand what real-world data reveals about the limits of autonomous AI and why the future of work will be built around human-AI collaboration rather than replacement.