Captives at a crossroads
An online panel hosted by Captive International involving some of our FORTY Under 40 judges underscored the urgent imperative to infuse the captive insurance industry with fresh, young talent.
The captive insurance industry is at a crossroads, facing the dual challenge of an ageing workforce and the need to attract young talent.
That was the message from an online panel hosted by Captive International involving a group of judges involved in selecting the final 40 young executives in this year’s FORTY Under 40 publication.
Phil Giles, chief growth officer for accident and health at Skyward Specialty Insurance, acknowledged the strides the industry has made but noted more can be done. “The captive industry has been one of the most dynamic and emerging segments of the commercial insurance world for many years,” he said, before warning that captive industries have traditionally struggled to attract young professionals compared to other segments of the financial services world. However he added that partnerships with universities and increased internship programmes have started to make a difference.
Anne Marie Towle, global captive solutions leader at Hylant, echoed Giles' sentiment. “There's never enough in whatever we do, but I certainly feel as if the last five to ten years have seen a greater outreach,” she said. Towle has been a driving force behind initiatives such as Amplify Women and NEXTGen for CICA, aimed at broadening access and awareness about captive insurance careers. “It's imperative for us to continue sending the message and to attract and develop young talent," she added. “It’s about spending the time to mentor and educate them on the benefits and diverse career paths the industry offers.”
“The captive industry has been one of the most dynamic and emerging segments of the commercial insurance world for many years.” Phil Giles
Gary Osborne, vice president at Risk Partners, highlighted the importance of associations in this effort. He pointed out that the South Carolina Captive Insurance Association put a lot of effort into setting up a scholarship with the University of South Carolina. “With a little prodding from this old soul, they gave up $100,000 to get a scholarship going,” he said. Other states like Tennessee, North Carolina and Vermont may follow.
Nate Reznicek, president and principal consultant at Captives.Insure, observed that recent efforts are beginning to bear fruit. “What we’re starting to see are the fruits of those labours, where young professionals realise this is a real opportunity,” he said. “As they spread the message, we hope to see a domino effect in attracting more talent.”
Mike Meehan, principal at Milliman, pointed out the need to differentiate captives from traditional insurance. Meehan said the captive industry gets lumped in with traditional insurance, which isn’t always seen as glamorous. However, he added: “But captives can be at the cutting edge, solving real-world problems like climate change or PFAs. It’s on us to make sure that message gets across.”
And Lesley Thompson, managing director of the Cayman Islands office at WTW, added that education is key. “The hardest thing is the lack of knowledge about what we do,” Thompson remarked. “In the Cayman Islands, we have one of the longest-standing scholarship programmes, and over the years we’ve funded over $5 million. More recently, we’ve shifted focus towards schools rather than universities, reaching students earlier.”
“More recently, we’ve shifted focus towards schools rather than universities, reaching students earlier.” Lesley Thompson
The importance of identifying young talent goes beyond filling vacancies. It’s about building a sustainable future. “If you find a talented individual and get them involved early, you can excite them about the work and show them a clear career path,” Meehan said. “If we don’t, they’ll leave for greener pastures.”
Osborne emphasised the value of nurturing talent early: “If you get them at 25 or 30, you can show them how creative and dynamic this industry is. When I started, medical stop loss in captives didn’t exist. Every year, there’s something new.”
Towle added a personal perspective, underscoring the importance of mentorship. “I want to retire some day!” she quipped. “It’s crucial to transfer knowledge and leave a legacy. I mentor people within my team and across the industry. We need to give young professionals leadership training and the tools to navigate and grow in this space.”
The captive insurance industry is undeniably evolving. With targeted outreach, scholarships, mentorship programmes and a renewed focus on education, industry leaders are sowing the seeds for the future. “We have to view ourselves as stewards of the industry,” Giles said. “It’s on us to perpetuate its sustainability by continuously developing new talent.”
The work is far from complete but, as the panel underlined, the industry is heading in the right direction – one mentorship, scholarship and internship at a time.
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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