The 2026 Executives to Watch: Travelers’ Dave Raymond : Risk & Insurance

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The captive insurance industry is growing and evolving rapidly, with companies searching for more creative and innovative ways to address risk than the traditional market has to offer. Leading his team and his clients through that landscape is Dave Raymond at Travelers.

Dave Raymond, vice president of specialty
group captives, Travelers

While he comes to the table with decades of industry expertise, the thing that makes Raymond so valuable to his partners is his strategic vision. The ability to anticipate market trends — including emerging risks and regulatory shifts — and think long-term about the role of a captive in risk management is a critical skill. His collaborative approach and dedication to building long-term relationships also means he can help broker partners and clients take the long view of their captive plan as well.

“Our captive clients retain risk with a vision for lowering their total cost of risk over time. So near term changes become less about what’s happening today and more about how to position the relationship for long-term success. Sharing this vision with some of the most talented brokers, agents, actuaries, tax…

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