Pragmaticlive

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 Manag