From: Captive International
One of the most pressing challenges facing the global captive insurance industry is the growing shortage of qualified talent. That was the urgent message from the panel discussion “Trailblazing Tomorrow: Leaders in Cayman Captive Insurance” at the Cayman Captive Forum 2025.
Moderated by Dan Towle, president of the Captive Insurance Companies Association (CICA), the conversation featured Harvey Gowers of KPMG, Alexandra Clynes of Campbells, Kyla MacDonald of Kensington Management Group and Giles Hobday of USA Risk Group, who shared candid reflections on workforce pressures, shifting generational expectations and strategies for cultivating the next wave of industry leaders.
Towle opened the session by noting that while the talent challenge affects the entire insurance ecosystem, its impact is acutely felt in specialised jurisdictions like Cayman. The irony, he explained, is that the crisis is partly a symptom of success: the captive industry continues to experience rapid growth, but the number of professionals entering accounting, law, actuarial science and related fields has steadily declined. “When we look around our offices, there’s a lot more grey hair than there used to be,” he said, emphasising the urgency of attracting younger professionals—and keeping them long enough to pass institutional knowledge forward.
For Gowers, who began his career with KPMG in the UK before moving to Cayman 11 years ago, the talent shortage is the result of broad demographic and cultural shifts. He highlighted that globally, far fewer young people are pursuing traditional professional pathways. The demand for CPAs, for example, vastly exceeds supply, even as expectations among new graduates evolve. Flexibility, mental-health support, rapid progression and technological integration now outrank the financial stability that once drew people to accounting and law.
