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John Rossman

Early Amazon Leader, Gates Foundation & T-Mobile Advisor, 4x Best-Selling Author

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John Rossman has spent his career at the intersection of bold strategy and disciplined execution — and he's learned, from the inside, what separates organizations that win from those that merely survive. As the executive who launched and scaled Amazon Marketplace — now responsible for more than half of all units sold on Amazon — Rossman didn't just witness one of the most disruptive business transformations in modern history. He engineered it. That experience forged a conviction he has carried through every engagement since. Great outcomes don't happen by accident. They happen by design. 

 

Today, John Rossman is the leading authority on high-stakes decision-making in an AI-driven era. Through his firm, Rossman Partners, he advises C-suite leaders navigating the decisions that define their organizations' futures — from major technology transformations to AI strategy to cultural reinvention. His clients have included T-Mobile, the Bill & Melinda Gates Foundation, Walmart, Microsoft, Nordstrom, and dozens of enterprises. 

 

Prior to founding Rossman Partners, he was a Partner at Arthur Andersen and later spent twelve years as a Partner at Alvarez & Marsal, one of the world's premier turnaround and restructuring firms. He has served in senior advisory and interim executive roles, including as CIO and senior technology advisor at the Gates Foundation and senior innovation advisor at T-Mobile. He is the bestselling author of four books: The Amazon Way, Think Like Amazon, The Amazon Way on IoT, and Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era. The Amazon Way has been translated into 13 languages and remains one of the most widely read business leadership books of the digital era. He also writes The Digital Leader: A Big Bet Briefing, a popular Substack newsletter read by executives navigating transformation in the AI era. 

 

Rossman is not an academic. He is not a pundit. He is an operator who has done the work, led the teams, made the high-stakes calls, and helped hundreds of organizations find the clarity and courage to do the same. His keynotes are known for their rare combination of intellectual rigor and immediately actionable frameworks — content that leaders are still referencing and applying long after the event ends. 

 

He has been featured in The New York Times, Bloomberg, CNBC, BBC, and GeekWire, and has delivered hundreds of keynotes for organizations including Citibank, Microsoft, Nordstrom, Starbucks, Fidelity, Novartis, Chick-fil-A, and Verizon. John Rossman holds a BS in Industrial Engineering from Oregon State University. If you want him to open up, ask him about water polo, his family, or his French Bulldog, Bossman Rossman.

Speaking Topics

From Winning To Winning Big In The AI Era: Why Category Leaders Fail—and How To Build The Next Chapter Of Growth

The most dangerous position in business isn't falling behind—it's assuming past success guarantees future relevance. This high-energy keynote exposes the hidden forces of loss aversion, short-term thinking, and corporate inertia that quietly erode competitive advantage. John delivers a battle-tested playbook for turning ambitious AI and transformation goals into systematic reinvention that drives board-level growth.

Customer Obsession — The Amazon Way: The Difference Between Inspiring Your Team And Transforming Your Company

Customer-centric companies talk about the customer. Customer-obsessed companies build every system, decision, and incentive around them. Drawing from his bestseller The Amazon Way, John reveals how to implement Amazon's leadership principles as a true operating system—where consistent innovation and relentless execution become inevitable, not aspirational.

High-Stakes Decision Making For Systematic Transformation: Stop Treating Billion-Dollar Bets Like Routine Budget Line Items

Most transformations fail not because the strategy was wrong—but because the decision-making process was built for routine choices, not transformational ones. Based on his book Big Bet Leadership and frameworks proven at T-Mobile and the Gates Foundation, John delivers a systematic playbook for making the decisions that win customers, rally employees, and reward investors.

Healthcare Transformation — The Amazon Way: Patient Outcomes And Operational Excellence Are Not A Trade-Off

Healthcare leaders face a unique paradox: reduce cost, improve outcomes, and navigate decades of entrenched regulation—simultaneously. John brings Amazon's principles of customer obsession and systematic decision-making directly to healthcare's hardest problems, giving leaders a proven lens for solving challenges that traditional healthcare strategies simply cannot address.

Close The Transformation Execution Gap — The Playbook Of Champions: Strategy Dies In Execution. Here's How To Make Sure Yours Doesn't.

Brilliant strategies fail every day—not in the boardroom, but in the handoff to reality. This keynote reveals the specific mechanisms top-tier companies use to bridge the gap between strategic intent and operational results. Learn how to build accountability, velocity, and discipline without adding bureaucracy or burning out your best people.

The Future Of Work — High-Performance Teams: Build Teams That Thrive In Complexity, Deliver Under Pressure, And Keep Top Talent

AI workflows, permanent hybrid structures, and the relentless demand for speed have permanently changed what it means to lead a high-performing team. John delivers concrete, immediately implementable mechanisms for building teams that thrive in complexity, deliver under intense pressure, and retain exceptional talent—without requiring a massive enterprise overhaul.

What's The Future Of Your Industry — Think Like Amazon: See The Reinvention Coming Before Your Competitors Do

Every industry is being reinvented. The only question is whether you'll lead that reinvention or react to it. Based on his bestseller Think Like Amazon, John teaches leaders how to adopt Amazon's strategic lens—spotting where industry value will shift next, identifying what customers will want before they know it themselves, and turning disruption into durable competitive advantage.

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Testimonials

“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.”

“The audience LOVED your leadership keynote and they took away many key learnings that they hope can be applied moving forward.”

"The Big Bet Leadership keynote delivered an unparalleled journey through innovation and leadership excellence. Its profound insights have invigorated our team, equipping us to navigate our industry with newfound clarity and velocity. This keynote set a new benchmark for our team’s leadership excellence. John was incredible in preparing & interacting with our team!"

"I learned more from an hour with John than I did from my NYU MBA"

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