What do Frank Sinatra’s bulletproof vest, the Rolling Stones’ backstage doctor, and a Japanese insurance giant have in common? They’re all part of Chris Williams’ journey leading Tokio Marine’s international business across 40+ countries.

When Chris Williams took on the challenge of leading Tokio Marine’s international business, he stepped into a role that would reshape one of the world’s most respected insurance organizations. From navigating billion-dollar acquisitions to managing across global markets, Chris brings a rare perspective on how to unify cultures, retain leadership after mergers, and build long-term trust in a global framework.

In this conversation, Chris sits down with Ward and Matt to share hard-earned lessons from decades of transformation. He explains what happens when you ignore your gut instinct, why culture fit can make or break an acquisition, and how international experience builds credibility in a world of unpredictable risks. Chris also opens up about the importance of nurturing rising stars, addressing talent mismatches quickly, and why keeping local leadership empowered is crucial to sustaining growth.

Whether you’re preparing your business for the next acquisition, learning how to strengthen global teams, or simply looking for ways to futureproof your strategy, Chris’s insights reveal why clarity, consistency, and communication matter more than ever in times of change.

CHAPTERS:

00:00:00 – Important Thoughts on Growing Your Business

00:00:36 – Meet Chris Williams of Tokio Marine

00:01:29 – Explaining Specialty Insurance and Unique Polices

00:07:04 – How an Australian Became a Global Insurance Leader

00:07:22 – Tokio Marine’s Expansion and Diversification, HCC Acquisition

00:11:12 – Breaking Silos, Retaining Leaders, and Building Global Connection

00:16:03 – Understanding Japanese Business Culture 

00:18:04 – Post-Merger Integration and Employee Trust

00:21:08 – Building Local Leadership with Global Support

00:23:09 – Leadership Lesson: Following Your Gut

00:26:47 – Advice for Future Leaders: International Experience

00:32:40 – The Guardrails Process and Messaging with Ward

00:35:17 – Keeping Japan at the Heart of Global Strategy

00:38:30 – Biggest International Risks and Challenges Ahead

00:40:36 – Closing Reflections

Topics Discussed: 

• Trusting your instincts and following your gut (what happens when you don’t)
• What do when the culture or leadership is no longer the right fit for the company
• How to maintain local management within a global framework 
• Understanding the people you’re working with, both internally and globally
• Why international experience is important to understanding diverse cultures 
• Nurturing rising stars with structured training (and how to navigate talent mismatches)
• Futureproofing your business and global relations to prepare for unforeseen challenges

About Rethink Change:

When growth is stagnant, culture’s a mess, the brand’s adrift, and the board wants miracles by Monday, Pennebaker’s podcast, Rethink Change, is where innovators and disruptors go for clarity.

Hosted by Founder Ward Pennebaker and President Matt Pennebaker, this podcast delivers sharp insights from battle-tested leaders who’ve navigated chaos and turned challenge into momentum. You’ll hear from executives from startups to global behemoths, from a wide range of industries. No fluff. All results. These conversations reveal what actually works, enabling you to think differently and act smarter.

Get Connected with Rethink Change:

• Website: https://www.pennebaker.com/podcast
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