Big Bet Introduction Video

How’s your digital transformation, growth strategy, operating model transition or AI strategy going? Over 80% are considered failures, with only 0.5% of major initiatives deliver on time, on budget and deliver expected benefits. Big Bet Leadership is a playbook for you to become a transformational leader — a Big Bet Legend. Listen to this short video to get started.

Big Bet Leadership emerges as a transformative playbook designed for leaders navigating the complex terrain of digital transformation, growth strategies, operating model transitions, and AI implementations. Authored by John Rossman and Kevin McCaffrey, seasoned experts in leading high-stakes transformations, this book is a clarion call to those seeking to steer their organizations towards unprecedented success in an era where the majority of major initiatives falter. With over 80% of digital transformations and strategic initiatives falling short of their goals, and a mere 0.5% delivering on time, within budget, and achieving expected benefits, Big Bet Leadership offers a beacon of hope and a methodical approach to bucking this trend.

At the heart of Big Bet Leadership lies the conviction that the path to becoming a transformational leader—a Big Bet Legend—requires more than just adherence to conventional management wisdom. It demands a radical rethinking of how leaders approach big bets. These are not just any initiatives, but the kind that have the potential to redefine the trajectory of your organization. Rossman’s insights are grounded in his extensive experience, including his tenure at Amazon, where he was instrumental in developing and executing the marketplace model and enterprise services, which have since become benchmarks for successful digital transformation.

The book is structured around the three critical habits of Big Bet legends: creating clarity, maintaining velocity, and prioritizing risk and value. Perhaps most critically, the book delves into the art of prioritizing risk and value. This involves a nuanced understanding of where to focus your efforts and resources to maximize impact while mitigating potential downsides. It’s about making informed bets, leveraging data and insights to navigate uncertainty, and being prepared to pivot when circumstances demand.

In this short video, John Rossman invites you to embark on a journey to becoming a Big Bet Legend. It’s an opportunity to learn from one of the best in the business, to challenge the status quo, and to lead your organization into a future defined by bold ambitions and transformative achievements. Listen closely, for the path to legendary leadership begins here.