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How to Build a Scalable Strategy for Big Bets and Bold Moves with John Rossman
In this episode, Rebecca Hastings sits down with John Rossman — former Amazon executive, Managing Partner at Rossman Partners, and author of Big Bet Leadership and The Amazon Way series. They unpack what it really takes to drive transformation in high-stakes, high-ambiguity environments.
John draws from his time launching and scaling the Amazon Marketplace and his advisory work with Fortune 500 leaders to explain how bold ambition, when paired with strategic discipline, is the winning formula for transformation that delivers.
Whether you’re a founder at a fast-growing AI startup or a C-suite exec navigating transformation at scale, this episode arms you with a practical toolkit for making confident decisions and leading change that sticks.
Topics Covered:
- Why “big bets” aren’t about gambling — they’re about calibrating ambition with controlled risk
- The concept of the Big Bet Vector — clarity on the problem + clarity on the future state
- Avoiding transformation theatre and analysis paralysis
- Why velocity beats perfection in decision-making
- Systems thinking, wicked problems, and the power of the “Three Futures” exercise
- Common reasons transformations fail — and how to avoid them
Episode Highlights:
- 00:57 — Intro to John Rossman and “Big Bet Leadership”
- 03:10 — Are we in uniquely turbulent times? (Spoiler: not really.)
- 05:48 — Why companies stall despite big ambitions
- 08:25 — The real questions leaders must answer before executing transformation
- 13:11 — What kind of leaders thrive during transformation?
- 17:32 — The Three Futures exercise for effective executive alignment
- 23:41 — The danger of “all hat, no cattle” innovation
- 26:30 — How to manage a portfolio of big bets effectively
- 31:48 — Playing chess, not checkers: systems thinking in action
- 34:52 — Financial projections vs. outcome-based thinking
- 38:57 — Why many transformations fail before they start
- 41:07 — Big Bet GPT: John’s AI-powered strategy tool
- 42:19 — Why speed matters more than ever
About John Rossman:
John Rossman is the Managing Partner at Rossman Partners, a former Amazon executive, and the author of the bestsellers Think Like Amazon and Big Bet Leadership. At Amazon, he led the launch of the Amazon Marketplace. Today, he advises leaders at global enterprises on strategy execution, digital transformation, and innovation leadership.
🔗 Resources & Links:
- John’s Book: Big Bet Leadership
- Lucent AI Salary Guides: https://bit.ly/DataAILeadershipGuide2025
Rebecca Hastings, Founder and Director at The Lucent Group
Connect on LinkedIn: https://www.linkedin.com/in/hastingsrebecca/
Would you like to be a guest? Book a time to speak with Rebecca: https://calendly.com/rebeccahastings/discovery-call
The Lucent Group Ltd website - https://www.thelucentgroup.co.uk/
The Lucent Perspective website - https://thelucentperspective.com/
Rebecca has extensive talent and executive search experience supporting digital and technology businesses through complex changes and fast-paced scale-up periods. She works with businesses advising on C-level, technical, sales and commercial appointments, workforce planning, strategic talent management, recruitment processes and associated technology and employer brand development.
View all episodes
By Rebecca HastingsIn this episode, Rebecca Hastings sits down with John Rossman — former Amazon executive, Managing Partner at Rossman Partners, and author of Big Bet Leadership and The Amazon Way series. They unpack what it really takes to drive transformation in high-stakes, high-ambiguity environments.
John draws from his time launching and scaling the Amazon Marketplace and his advisory work with Fortune 500 leaders to explain how bold ambition, when paired with strategic discipline, is the winning formula for transformation that delivers.
Whether you’re a founder at a fast-growing AI startup or a C-suite exec navigating transformation at scale, this episode arms you with a practical toolkit for making confident decisions and leading change that sticks.
Topics Covered:
- Why “big bets” aren’t about gambling — they’re about calibrating ambition with controlled risk
- The concept of the Big Bet Vector — clarity on the problem + clarity on the future state
- Avoiding transformation theatre and analysis paralysis
- Why velocity beats perfection in decision-making
- Systems thinking, wicked problems, and the power of the “Three Futures” exercise
- Common reasons transformations fail — and how to avoid them
Episode Highlights:
- 00:57 — Intro to John Rossman and “Big Bet Leadership”
- 03:10 — Are we in uniquely turbulent times? (Spoiler: not really.)
- 05:48 — Why companies stall despite big ambitions
- 08:25 — The real questions leaders must answer before executing transformation
- 13:11 — What kind of leaders thrive during transformation?
- 17:32 — The Three Futures exercise for effective executive alignment
- 23:41 — The danger of “all hat, no cattle” innovation
- 26:30 — How to manage a portfolio of big bets effectively
- 31:48 — Playing chess, not checkers: systems thinking in action
- 34:52 — Financial projections vs. outcome-based thinking
- 38:57 — Why many transformations fail before they start
- 41:07 — Big Bet GPT: John’s AI-powered strategy tool
- 42:19 — Why speed matters more than ever
About John Rossman:
John Rossman is the Managing Partner at Rossman Partners, a former Amazon executive, and the author of the bestsellers Think Like Amazon and Big Bet Leadership. At Amazon, he led the launch of the Amazon Marketplace. Today, he advises leaders at global enterprises on strategy execution, digital transformation, and innovation leadership.
🔗 Resources & Links:
- John’s Book: Big Bet Leadership
- Lucent AI Salary Guides: https://bit.ly/DataAILeadershipGuide2025
Rebecca Hastings, Founder and Director at The Lucent Group
Connect on LinkedIn: https://www.linkedin.com/in/hastingsrebecca/
Would you like to be a guest? Book a time to speak with Rebecca: https://calendly.com/rebeccahastings/discovery-call
The Lucent Group Ltd website - https://www.thelucentgroup.co.uk/
The Lucent Perspective website - https://thelucentperspective.com/
Rebecca has extensive talent and executive search experience supporting digital and technology businesses through complex changes and fast-paced scale-up periods. She works with businesses advising on C-level, technical, sales and commercial appointments, workforce planning, strategic talent management, recruitment processes and associated technology and employer brand development.