Keynotes: The Playbook for High-Stakes Decisions in the AI Era
Your organization doesn’t need another inspirational talk. It needs an operating system for winning.
In an era of unprecedented disruption, your team’s ability to make high-quality, high-stakes decisions is the ultimate competitive advantage. Yet most leaders are navigating this landscape without a proven playbook, leading to stalled initiatives, wasted resources, and a massive "execution gap" between ambition and results.
John Rossman delivers more than a keynote—he delivers a battle-tested framework that equips your leaders with the tools and confidence to make winning bets. He provides a new language and a repeatable process for turning volatility from a threat into an advantage.
Is Your Organization Facing a Big Bet?
John’s keynotes are designed for leadership teams and organizations at a critical inflection point. He provides clarity and a path forward for leaders wrestling with challenges like:
The AI Execution Gap: You see the massive potential of Generative AI, but you’re struggling to de-risk investments and scale pilots beyond the lab .
Navigating Volatility: Your market is defined by constant change and uncertainty, and you need a reliable process for making clear, confident choices when the stakes are high .
Workforce Transformation: You need to make the right bets on talent, upskilling, and organizational design to build a culture that can win in an AI-native world .
Board & Investor Alignment: You need to communicate your high-stakes strategy to the board and shareholders with a framework that demonstrates rigor, clarity, and a focus on long-term value .
Signature Keynote Topics
Each keynote is customized to address your audience’s specific challenges and is delivered as a practical, engaging working session, not a passive lecture.
1. AI is the Ultimate 'Big Bet': A Leader's Playbook for Driving Real ROI
The potential for AI is massive, but 89% of pilots fail to scale. This keynote provides a practical operating system for de-risking your AI investments. Your audience will leave with a framework for identifying the right initiatives to fund, ensuring you scale the winners and kill the losers before they drain your resources. This is a talk about capital allocation and risk management for the most critical investment your company will make this decade.
2. Big Bet Leadership: How to Make Winning Decisions When the Stakes Are High
This keynote delivers the core, battle-tested methodology from the book Big Bet Leadership. John provides a repeatable process for making clear, confident, and decisive choices in the face of uncertainty. Your team will learn the tools and techniques—from writing a "Future Press Release" to defining the "Killer Feature"—that turn ambitious ideas into market-shaping realities. They will leave with a shared language and a powerful framework for their next major initiative.
3. The AI Culture You Need: The Talent and Organizational Bets to Win the Future
A legacy culture cannot execute a next-generation AI strategy. This keynote addresses the most critical factor for success: your people. John provides a clear framework for making the right decisions on leadership, upskilling, and organizational design to build a workforce that can thrive in an AI-native world . This talk moves beyond the technology to the human capital strategy required to build a lasting competitive advantage.
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. 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" and captured in his best selling books “The Amazon Way” and “Think Like Amazon”. As a former Managing Director at Alvarez and Marsal and now at Rossman Partners, he has guided C-suite leaders and boards through their most complex and urgent transformations.
Bring This Playbook to Your Team
John’s keynotes are a powerful catalyst for change, providing the concepts, tools, and inspiration to turn your organization’s biggest challenges into its greatest triumphs.
Connect with me to discuss your meeting or event.
Learn more at