An image of the Big Bet Leadership book.

“Wow! Our team loved John’s Big Bet Leadership presentation. The message was spot on for our digital journey. We are ordering more books now”

— Keith Nelson; Chief of Staff, Alcon
An image of the Big Bet Leadership book.

About the Book

Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era reveals the actionable playbook to become a systematic innovation and transformation winner. There are countless books making the case for digital transformation, innovation and business model reinvention, on agile frameworks and innovation programs and styles, and bountiful stories about the companies and leaders of both the disruptors and the disrupted. These works are important, but they are not sufficient.

Releases on February 27, 2024.


“90% of the world knows they need to change. Only 10% are ready to change. Big Bet Leadership is for that 10%”

— Mark Goulston, author of Talking to Crazy; Professor of of psychiatry, former FBI and police hostage negotiation trainer

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In an era where change is accelerating, this book is a beacon for those who choose to step forward, embrace the challenge, and tilt the odds of success to be in their favor.

Inside the Book

Drawing from first-hand executive experience at Amazon, Google, The Gates Foundation and T- Mobile, and having advised hundreds of companies, John Rossman and Kevin McCaffrey weave a compelling story with concepts, rules, techniques and resources, equipping business executives to become Big Bet Legends.

Despite overwhelming odds, with studies indicating a failure rate of over 70% in innovation and transformation initiatives, Rossman and McCaffrey argue that successful transformation is not only possible but can become a core competency. Dismissing many traditional corporate rules, policies and perspectives, they narrate an engaging perspective with principles and tactics that can be incorporated by leaders of companies. The book is complemented with online templates, examples and applications.

Broken into three sections – Big Bet Thinking, Big Bet Environment, and Big Bet Management – Big Bet Leadership is an invaluable guide presenting a comprehensive playbook for making strategic moves and digital transformations that can drastically reshape and enhance the prospects of an organization. 

Praise for Big Bet Leadership

Most books merely extol the virtues and mandate for transformation, urging you to transform without truly instructing how. Big Bet Leadership is a masterstroke, daring to present an empowering gameplan suited for digital transformations or any vital strategic initiative. It is more than just a call to action; it’s a blueprint for success. Bravo!

Jeff Dirks

CTO of Trueblue

Big Bet Leadership is a game changer for leaders looking to drive transformation and deliver remarkable results. Prepare to be inspired, challenged, and equipped with the tools to lead with purpose and deliver tangible outcomes.

Gary Michel

Former Chair and CEO of Jeld-Wen, Inc., Forbes Featured Author, Keynote Speaker, Director and Advisor

About the Authors

John Rossman

Managing Partner

John Rossman is a leadership development coach and business transformation advisor, keynote speaker and founder of Rossman Partners. He is an early Amazon executive with key responsibilities in launching the Amazon marketplace business in 2002, and author of the bestselling books, The Amazon Way and Think Like Amazon. He has advised and served as an interim leader to large enterprises such as the Gates Foundation, Microsoft and T-Mobile.

Kevin McCaffrey

Research and Development Partner

Kevin McCaffrey is an expert in Strategy Operations (StratOps), with a focus on the design of user-centered approaches to optimizing delivery of the most important strategic decisions that leaders must get right — decisions like allocating resources across a portfolio and placing Big Bets. He is a former McKinsey consultant and led strategy, operations and new business incubation functions at T-Mobile and Google. He is a Research and Development Partner at Rossman Partners.

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