Pragmatic Live’s Product Chat is a podcast focused on tackling the biggest challenges facing today‘s product management, product marketing, and other market and data-driven professionals with some of the best minds in the industry.
Episodes
Friday Feb 14, 2025
Friday Feb 14, 2025
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
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