The 2026 Executives to Watch: Travelers’ Dave Raymond

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 advisors, claims and risk control professionals servicing this industry is amazing,” Raymond said.

He has been praised by his broker partners not just for the development of unique captive models but also his willingness to listen and learn the details of potential clients’ operations and specific risk exposures. His attention to detail and willingness to think outside the box has made him the go-to guy for captive knowledge for many brokers and risk professionals in the industry.

“Carriers that understand your risk are better equipped and more likely to stay the course through short-term challenges,” he said. “Considering the long-term nature of captive relationships, I would encourage risk managers to identify carriers who have the best understanding of the risks they need insured.”

Sharing Knowledge with the Next Generation

Raymond has also been generous with his knowledge of the captive industry, regularly giving guest lectures at the UConn School of Business. According to Shane Murphy, who teaches risk and insurance at the school, Raymond excels at grounding theories and concepts in real-life examples, making content relatable to students.

“When Dave describes the work he does at Travelers, it moves the students out of theory and into practical application. He’s been able to consistently demonstrate how an insurance career brings you closer to how a company runs. That’s what aspiring finance students want to hear,” Murphy said. “Dave shows them how the skills they are building in the classroom are relevant to employers like Travelers. They get a better sense of how to get hired.”

Just as he puts effort into cultivating relationships with business partners, Raymond also sets aside time to speak with students oneon-one, answering questions or explaining points in greater detail. Raymond similarly shares his knowledge as a speaker at annual industry events like VCIA, Cayman Captive Forum, CICA, and RISKWORLD. His insights have helped to shape best practices in captive development and management.

As a leader, his forward-looking view and dedication to shaping the future of the captive landscape make him one to watch. &

Dave Raymond has been selected as a 2026 Risk & Insurance® Executive to Watch. To see the other executives selected this year, visit here.