Hi everyone —

This week on Lead The Machine, I’m truly honored to share my conversation with Brian Duperreault — former CEO & Chairman of AIG, and a leader who has shaped modern insurance through CEO roles at Marsh & McLennan, ACE (now Chubb), and Hamilton. He’s currently Executive Chairman of Cedar Trace.

Brian and I begin where real transformation always begins: people. We talk about why talent remains a true C-suite priority, and why it becomes even more urgent in the age of AI. This is personal for me: Brian and I worked together through the Insurance Careers Movement (ICM), a CEO-led collaboration created to attract and develop the next generation of insurance professionals, including the Emerging Leaders Conference.

I helped co-found ICM, now in its 11th year, which is led by the American Casualty Property Insurance Association, The Jacobson Group and AM Best. Over 1,000 companies from 20 countries participate each February for Insurance Careers Month.

Be optimistic and pragmatic

From there, we turn to AI as the next major technology shift leaders must navigate. Brian offers a grounded perspective: big tech transitions are often slower than we expect, deliver less than we assume early on, and cost more than planned. But they are still inevitable.

“I’m an optimist,” Brian shares. The leaders who win are the ones who engage early, shape adoption responsibly, and keep their organizations relevant as the competitive bar rises.

We also discuss how AI shows up in practical ways: augmentation over replacement, using technology to reduce drudgery, improve decision quality, and free people to focus on judgment and relationships — the parts of the work that actually differentiate.

Finally, Brian shares a simple message for professionals coming up the ranks: do your job well, stay curious, raise your hand for the hard work, and become the person leaders can count on during change. In a world where tools evolve quickly, those habits are what keep you relevant.

It’s not often we get to hear from a business titan in an informal setting. Brian’s broad view of AI, risk, and the leadership talent required to navigate AI offers perspective and forward-thinking ideas. His recent biography Faith & Purpose: The Life & Vision of Insurance Icon Brian Duperreault, written by Wendy Davis Johnson (also an ICM co-founder) is well worth reading.

Thanks for engaging with Lead The Machine.

— Kirstin

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