In this episode of Let’s Take a Walk, Charlie Feld is joined by John Rossman, former Amazon executive and author of Big Bet Leadership, for a wide-ranging conversation on what it really takes to lead transformation in the AI era. Together, they explore why most large transformations fail, how leadership for operational excellence differs from leadership for high-risk innovation, and why architecture, storytelling, and long-term stewardship matter more than ever. Drawing on lessons from decades of CIO experience, this conversation challenges leaders to stop waiting, start experimenting, and build organizations designed for change.

https://johnrossman.com/

https://www.linkedin.com/in/john-rossman/