About The Digital Leader: A Big Bet Briefing on Strategy and AI
In an era of AI-driven disruption, the difference between market leadership and obsolescence comes down to one thing: the quality of your high-stakes decisions.
Yet most leadership teams are navigating this new landscape without a playbook. They face a massive "execution gap," where great ideas stall and 89% of AI pilots fail to scale. The result is wasted capital, missed opportunities, and strategic paralysis.
This newsletter is the playbook to close that gap.
The Digital Leader: A Big Bet Briefing on Strategy and AI is a weekly dispatch for C-suite executives, board members, and senior leaders who need to make winning bets with clarity, velocity, and confidence.
Each week, you get one actionable idea, proprietary framework, or battle-tested tool designed to help you de-risk your most critical initiatives. This isn’t theory; it’s a set of practical instruments from the front lines of digital transformation, inspired by the operating models of the world’s most innovative companies.
When you subscribe, you will learn how to:
De-Risk Your AI Investments: Get proven frameworks to ensure you scale the winners, kill the losers, and generate real ROI from the biggest technological shift of our time.
Turn Volatility into Advantage: Receive a repeatable process for making clear, confident choices when the stakes are high and the future is uncertain.
Make the Critical Talent Bets: Get a structure for making the right decisions on the leadership, skills, and organizational design required to win in an AI-native world.
About John Rossman
John Rossman is a leading authority on high-stakes decision-making in the AI-driven era and the author of Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era and the bestselling books The Amazon Way and Think Like Amazon.
He developed his battle-tested playbook as an early Amazon executive who launched and scaled the Amazon Marketplace—one of the company’s most successful "Big Bets". As a Managing Director at the global consulting firm Alvarez and Marsal, he has guided C-suite leaders and boards through their most complex and urgent transformations.
This newsletter is where he shares his most valuable and exclusive insights from that work.
Subscribe to Become a Member
The best way to engage with this work is to subscribe. Join a community of thousands of senior leaders and get the frameworks you need to win your next Big Bet.
Free Subscription: You'll receive the flagship weekly briefing with actionable frameworks and analysis.
Premium Subscription: For leaders who need to execute, a paid subscription unlocks the full playbook:
Exclusive, in-depth strategic briefings applying the Big Bets System™ to specific, high-value industries.
A library of downloadable, actionable tools and templates directly from the Big Bet Leadership playbook.
Monthly live, subscribers-only video calls where members can get direct answers to their specific strategic challenges.
My most recent book is Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digtal Era.
I co-authored Big Bet Leadership with Kevin McCaffrey. Kevin ran new business incubation at T-Mobile, then ran a strategy operations team at Google Ads and is a Harvard and U of Chicago graduate. I worked closely with Kevin at T-Mobile for three years building an innovation and business incubator at T-Mobile.
Many of the stories and lessons in Big Bet Leadership come from our experience at leading new business incubation and innovation at T-Mobile.
Geekwire had Kevin and I on for a podcast interview. This is a great listen from the both of us.
