Big Bet Leadership: How to Win in the Hyper-Digital Era with John Rossman

What separates the companies that succeed in digital transformation from the 73% that fail to deliver any business value? 

In this episode, host Rebecca Kalogeris sits down with John Rossman, former Amazon executive, best-selling author, and renowned business advisor, to discuss his latest book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era. 

John shares his expertise on Big Bets—high-stakes initiatives designed to tackle wicked problems and drive disruptive innovation. He explains why most Big Bets fail (hint: it’s a lack of clearly defined vectors) and outlines a structured approach for leaders looking to manage risk, navigate uncertainty, and drive transformation successfully. 

From his time launching Amazon Marketplace in 2002 to advising the Gates Foundation and T-Mobile, John has seen firsthand what it takes to execute ambitious, high-risk initiatives. He introduces the Big Bet Leadership Framework, which focuses on three pillars: Thinking, Environment, and Management—all of which are essential for making bold moves with confidence. 

Tune in for actionable insights on "thinking in memos," testing assumptions with a "Think Big, Bet Small" approach, and mastering the art of being a Chief Repeating Officer to drive alignment across teams. 

For free templates and resources, visit www.bigbetleadership.com 

For detailed takeaways, show notes, and more, visit: www.pragmaticinstitute.com/resources/podcasts 

Pragmatic Institute is the global leader in Product, Data, and Design training and certification programs for working professionals. Learn more at www.pragmaticinstitute.com.