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.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
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CrimeLess: Hillbilly Heist
It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.