In this episode of Product Chats, John Rossman, former Amazon executive and business transformation expert, joins host Rebecca Kalogeris to discuss how leaders can identify, manage, and execute Big Bets—high-risk, high-reward initiatives that drive significant business impact. Drawing insights from his latest book, Big Bet Leadership, John provides a structured framework for navigating complex digital transformations.
Key Takeaways:
- Big Bets Solve Wicked Problems – Disruptive products require tackling high-risk, high-reward initiatives—not incremental improvements.
- Thinking in Memos – Communicate strategic thinking effectively through structured memos like the “What Sucks Memo” (problem framing), the “Outcome Definition Memo” (vision-setting), and the “Competitive Set Memo” (learning from others).
- Think Big, Bet Small – Prioritize testing the most critical risks first with small, controlled experiments before scaling.
- Managing Big Bets – Success isn’t just about execution. Leaders must continuously assess whether to continue, pivot, or kill initiatives—and understand that only one of those is a failure.
Guest Bio:
John Rossman is a writer, business advisor and leadership keynote speaker. He was an early Amazon executive who played a key role in launching the Amazon marketplace business in 2002. He has served as the senior technology advisor at the Gates Foundation and senior innovation advisor at T-Mobile.
He is also a 4x best-selling author and his new book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, is an actionable guide for leaders who want to succeed in complex transformations.
For free templates and resources, visit www.bigbetleadership.com
Connect with John at www.johnrossman.com and www.rossmanpartners.com
ABOUT PRAGMATIC INSTITUTE:
Since 1993, Pragmatic Institute has provided training and professional development for product, design, and data professionals. Our comprehensive methods and Pragmatic Framework equip professionals with the skills to accelerate innovation, increase customer satisfaction, and bolster revenue. We offer online, in-person, and on-demand courses taught by industry experts with decades of experience.
- Learn more about how to boost your PM skills with our workshops
- Explore our training and certification paths
- Learn about Pragmatic Institute
- Subscribe to our YouTube Channel
