Captives must confront a talent crisis
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.
Cayman faces the additional hurdle of geographical scale; no matter how strong local recruitment becomes, the island will always rely on overseas hiring to fill specialised roles.
While the legal profession faces similar recruitment constraints, Clynes underscored that the skills gap is not only technical but also adaptive. Younger lawyers must learn how to use AI effectively, but that requires first understanding the legal reasoning and drafting fundamentals that the technology is built to augment. The hunger for remote work, entrepreneurial career paths and digital independence has also reshaped what the next generation expects from the workplace.
For captive managers, MacDonald explained, technical credentials alone are no longer enough. Professionals entering the industry mid-career typically already possess accounting or legal qualifications. What managers now look for are leadership traits: communication, relationship-building, confidence, adaptability and the ability to present to boards and clients. Hobday echoed this point, noting that captive management requires a uniquely diverse skill set, ranging from meticulous financial oversight to high-stakes boardroom communication. Yet because few people grow up knowing what captive insurance is, firms must cast a wide net—and often hire from one another—to find strong candidates.
With recruitment challenges widely acknowledged, the panel turned to retention. Cayman firms cannot afford to lose the people they invest in, and the speakers shared approaches that have helped them create environments where staff feel valued and supported. MacDonald emphasised Kensington’s strong focus on wellness, community and psychological safety. Employees work hard, she noted, especially with the travel demands of the industry, so investing meaningfully in well-being pays long-term dividends. Hobday described USA Risk Group’s hybrid work policy, flexible culture and open-door leadership as key contributors to morale and loyalty.
Another critical element is trust. Clynes explained that junior lawyers flourish when given ownership over tasks, client exposure and the confidence that senior colleagues will support—not micromanage—their development. As juniors become more capable, they step into new responsibilities at a pace that prepares them to inherit client relationships smoothly.
Succession planning was also flagged up as a key issue. With a large portion of the industry approaching retirement age, companies must look ahead not just to their next leader, but the leader after that. For Gowers, structured performance management is only part of the solution. High-potential employees must also gain real-world exposure: joining client meetings, attending conferences, shadowing senior staff and participating in local organisations such as IMAC and CICA. Hobday stressed that investing in travel, conferences and professional designations is essential—not optional—if firms want emerging talent to reach their full potential.
In closing, Towle urged the industry to “tell its story.” Unlike the mass-market caricature of insurance—the gecko, the emu, “Jake from State Farm”—the captive sector offers intellectually challenging, globally connected, dynamic careers with significant upward mobility. And because the industry is small, the impact of every new entrant is meaningful.
Did you get value from this story? Sign up to our free daily newsletters and get stories like this sent straight to your inbox.
