Future Of Work Podcast How AI Is Reshaping Freelance Work with Dave Bottoms
In this episode of The Future of Work® Podcast, host Frank Cottle welcomes Dave Bottoms, SVP of Product and GM of Marketplace at Upwork, to discuss how the world’s largest talent platform is being reshaped by AI. With two decades of experience leading product at Meta, Dropbox, and Yahoo, Dave unpacks how platforms like Upwork are transitioning from simple job boards to intelligent, AI-powered ecosystems.
From UMA — Upwork’s AI companion — to the rise of fractional executives and agentic project orchestration, this conversation dives deep into what it means to build lean, borderless teams. Whether you’re a founder hiring globally or a freelancer navigating a shifting landscape, Dave’s insights reveal the future of digital labor and what work will look like in the AI-augmented era.