Exceeding Expectations
Why Your AI Pilots Aren’t Scaling
October 27, 2026
Most failed AI deployments aren’t technology failures. They’re management failures wearing an expensive disguise. In this episode of Exceeding Expectations, host Laurel Rockall sits down with Elaine Barsoom, former Global Head of AI and Tech Innovation Partnerships at Nike, innovation leader at American Express, and now Founder of Waveco, to unpack why so many enterprise AI pilots impress in the room but never change how a company actually runs.
Most failed AI deployments aren’t technology failures. They’re management failures wearing an expensive disguise. In this episode of Exceeding Expectations, host Laurel Rockall sits down with Elaine Barsoom, former Global Head of AI and Tech Innovation Partnerships at Nike, innovation leader at American Express, and now Founder of Waveco, to unpack why so many enterprise AI pilots impress in the room but never change how a company actually runs.

What You’ll Learn:

Elaine Barsoom is a two-decade enterprise operator turned advisor, working at the intersection of emerging technology and organizational transformation. She served as Global Head of AI and Tech Innovation Partnerships at Nike and held innovation leadership roles at American Express before founding Waveco, her human-centered AI advisory practice. She is also a Venture Partner at Silicon Foundry, where she advises senior leaders and investors on turning AI ambition into operational reality. Elaine's work focuses on the uncomfortable but essential questions behind enterprise AI: governance, decision rights, workflow redesign, and the leadership courage required to move from pilot to real transformation.

Episode Resources: