Fight to retain your talent
Finding and recruiting talent is one thing, but retaining it in a world of changing workplace practices is something else, according to an online panel for FORTY Under 40.
In the wake of the great resignation and Covid-19, the captive insurance industry is facing multiple challenges around not just attracting, but also retaining, young talent while adapting to an evolving work environment.
A recent Captive International online panel of FORTY Under 40 judges highlighted the importance of mentorship, flexibility and fostering meaningful connections within the workplace.
Lesley Thompson, managing director, Cayman Islands, at WTW, noted that the pandemic-induced shift towards flexible work arrangements has brought both benefits and challenges. “I think there's been some good things that came out of Covid because we moved away from the ‘it has to be nine to five, and it has to be in the office’, and I think that's created a lot of flexibility,” she said. However, she acknowledged the difficulties in training new recruits remotely, stressing the importance of absorbing knowledge by osmosis in an office environment. “It's that sort of absorbing knowledge by osmosis. You're picking it up just because you're listening to the environment around you,” she added.
Gary Osborne, vice president at Risk Partners, echoed these sentiments, expressing concern that remote work might disadvantage younger employees. “We're almost doing young people a disservice if we allow them to work remotely. For the young people to succeed, they've really got to get some hands-on learning,” Osborne said. He suggested a hybrid approach, encouraging young professionals to spend one to two months in an office environment to gain foundational skills before transitioning to remote work.
"For the young people to succeed, they've really got to get some hands-on learning. "Gary Osborne
The panel also tackled the looming talent gap exacerbated by the ‘great resignation’ and the imminent retirement of seasoned professionals. Michael Meehan, principal at Milliman, remarked, “We do have a talent gap... we need to replenish [it] with regards to the next gen coming in.” Meehan praised initiatives that expose young professionals to real-world scenarios early in their careers, citing Hylant’s practice of involving interns and early-career employees in client-facing projects. “To me, that's the best way to learn – to hear what's happening in the industry, hear how to interact with clients and hear what some of the challenges are being faced by our peers, our clients, our competitors.”
Anne Marie Towle, global captive solutions leader at Hylant, underscored the need for early exposure and ongoing support. “If they are going to be client-facing, they need to be doing and experiencing that really from day one. Knowing they have the support of me or other leaders on my team is critically important so they feel comfortable,” she said.
Another crucial aspect of talent retention lies in understanding young professionals' motivations. Nate Reznicek, president and principal consultant at Captives.Insure, pointed out that younger generations seek more than just a pay cheque; they crave purpose and personal growth. “They are looking to do things to enter a career that helps them serve a greater purpose. The more we connect with their goals and aspirations, the better chance we have at keeping them in the industry,” he explained.
"If new recruits are going to be client-facing, they need to be doing and experiencing that really from day one." Anne Marie Towle
The conversation also touched on creating engaging career paths. Phil Giles, chief growth officer at Skyward Specialty Insurance, emphasised the creative opportunities within captive insurance. “The captive industry is a perfect outlet for exercising creativity. The application for designing and implementing new coverages is almost endless, from cyber and parametric to medical stop loss and pandemic-related coverages.”
Furthermore, the panel recognised the value of mentorship and long-term career development. Mike Meehan shared his personal journey, crediting his longevity at Milliman to a supportive mentor. “I had a mentor that was with me for a large portion of my career. That relationship kept me engaged and constantly learning.”
Finally, the importance of fostering open communication within organisations was highlighted as a key to talent retention. Thompson remarked, “It's on all of us to foster those conversations. If it isn't the right role, then helping them find the right one for them – whether it be within your organisation, within the industry, or even outside the industry – is important.”
In essence, the captive insurance industry stands at an inflection point. As the workforce evolves, so must the industry's strategies for nurturing talent. Whether through hybrid work models, early exposure to client-facing experiences or providing meaningful career paths, the future success of the industry hinges on its ability to adapt and support the next generation of professionals.
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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