Talent wanted: why captive insurance is the career you didn’t know you needed
If you want unmatched creativity, innovation and growth potential, captive insurance is for you. Captive insurance might not be the most obvious career choice, but for those who venture into it – be it by chance or design – it offers a dynamic blend of creativity, innovation and problem-solving.
Captive insurance might not be the most obvious career choice, but for those who venture into it – be it by chance or design – it offers a dynamic blend of creativity, innovation and problem-solving.
Captives International spoke with finalists from the Forty Under 40 competition, who shared their insights on why the field continues to inspire and challenge.
For many, entering the captives industry was serendipitous.
“The creativity behind captives’ investment considerations hooked me.” Dylan Feringa
Troy LePage, executive vice president and COO at HAI Group, admitted, “I didn’t leave college saying I want to go into insurance.”
Like others, he stumbled into the field and was captivated by its complexity: “Very early on, I knew it was an industry I wanted to stay in,” he added.
Now, eight years into his role, he thrives on creating insurance solutions for public and affordable housing.
Dylan Feringa, director, PNC Institutional Asset Management , also transitioned unexpectedly from broader asset management at PNC into insurance asset management with a focus on captive asset management.
“The creativity behind captives’ investment considerations hooked me. Captives touch so many sectors and offer solutions that are anything but stagnant,” he said.
“You’re never pigeonholed, and that makes you better at solving client problems.” Caroline Erdman
For others, the journey was more intentional.
Caroline Erdman, a captive consultant at Hylant, studied risk management and insurance in college, discovering her passion for captives through an internship. “It’s such an innovative field, offering constant variety and challenge,” she said.
Nick Frongillo, senior consulting actuary at Spring Group, was drawn by his love of mathematics. “Captives force you to learn,” he explained. “You need to understand programme structures, reinsurance and contracts, which makes the work incredibly dynamic.”
Why captive insurance?
Captive insurance stands out as an evolving and impactful industry, as Feringa explained: “You’re not just financing risk; you’re creating innovative solutions. The industry is ever evolving, and that’s what makes it so compelling.”
Erdman highlighted its versatility, working with clients ranging from manufacturers to stadium owners.
“You’re never pigeonholed, and that broad experience makes you better at solving client problems,” she said.
Frongillo added, “Every captive is unique. You’re designing tailored solutions for specific problems, which keeps the work exciting.”
“You’re designing tailored solutions for specific problems, which keeps the work exciting.” Nick Frongillo
The captive industry thrives on innovation and Frongillo shared a groundbreaking example: “We recently received Department of Labor approval to execute a pension transaction through a captive – it’s the first of its kind and was exciting figuring out.”
Feringa emphasised the creative use of captives’ balance sheets and the transformative potential of AI in risk management and modelling. “AI is driving critical thinking and furthering innovation across the sector,” he said.
LePage pointed to data analytics as a game-changer: “Insurance is built on data; tools such as data warehousing and AI are essential for staying competitive,” he noted.
Erdman emphasised the creativity in crafting unique coverages to address gaps left by standard policies. She also noted how older captives were adapting to include new risks such as voluntary employee benefits or innovative reinsurance structures.
Bringing in new talent
Despite all this innovation, challenges still persist.
Climate-related exposures, social inflation and cybersecurity threats are pressing concerns.
“Captives must adapt their coverage and reinsurance strategies to keep pace,” LePage admitted.
The talent gap also looms large, and Feringa identified mass retirements as a critical issue: “We need to educate people about captives and recruit new talent.”
“Tools such as data warehousing and AI are essential for staying competitive.” Troy LePage
Erdman added: “We’re in the golden age of captives, but without education, we risk stagnation.”
Despite challenges, the future of captive insurance is bright.
“Mass retirements are creating opportunities for growth. It’s exciting and rewarding for anyone entering the field,” Erdman said.
LePage highlighted the importance of outreach: “We’ve expanded our intern programme and actively engage with schools to showcase the industry’s potential.”
Even for mid-career professionals, the field holds unique appeal. “A risk manager with 20 years of experience might form their first captive and discover a whole new world,” Feringa noted.
While financial hurdles like inflation and high interest rates pose challenges, Frongillo remained optimistic. “The challenges we face today – financial, operational and generational – are also the catalysts for the industry’s continued growth and innovation.
The discussion concluded with LePage stating: “If I’d recommend this to my kids, I’d recommend it to anyone. Captive insurance is a career worth exploring.”
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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