FORTY under 40: Troy LePage
Troy LePage, chief operating officer, HAI Group.
Troy LePage began his career at Deloitte, where he spent around ten years auditing and consulting for a diverse range of insurance companies, including captives. In 2017, he joined HAI Group, a leading captive insurer specialising in public and affordable housing. Over the past eight years, he has taken on roles of increasing responsibility, culminating in his current position as the group’s chief operating officer and executive vice president.
How did you first become involved in captive insurance?
Early in my career, I was assigned to insurance clients and quickly developed a passion for the industry. This led me to work extensively with captives, including group captives, single-parent captives and reciprocals. When the opportunity to join HAI Group arose, it was a perfect fit – allowing me to apply my expertise in a mission-driven organisation dedicated to serving the public and affordable housing sector. Being part of a captive that directly supports the long-term stability of such an essential industry has been both rewarding and impactful.
What are the greatest challenges of working in this industry, and what do you find most rewarding?
One of the greatest challenges is navigating an ever-evolving regulatory landscape while ensuring captives remain effective and sustainable risk management solutions. The complexity of balancing compliance and financial stability, while delivering innovative risk strategies, requires adaptability and expertise.
It’s rewarding to know that our work helps create stability, resilience and long-term security for those we serve
However, the most rewarding aspect is seeing captives provide customised, cost-effective insurance solutions to organisations that might otherwise struggle to find adequate coverage.
This mission was a driving force behind HAI Group’s creation in the mid-1980s, and it remains at the core of what we do today. Being part of an industry that empowers organisations – especially those in the public and affordable housing sector – to take control of their risk management is incredibly fulfilling. It’s rewarding to know that our work helps create stability, resilience and long-term security for those we serve.
Would you recommend the captive insurance industry to young people as a future career path?
Absolutely. The captive insurance industry is an excellent career path for young professionals, offering diverse opportunities in underwriting, actuarial work, risk management, regulatory compliance and beyond. This sector is constantly evolving and in need of fresh talent to drive innovation and meet emerging challenges. With the industry’s continued growth, professionals entering can build rewarding, long-term careers with ample opportunities for advancement, specialisation and leadership. It’s a dynamic space where problem-solving and strategic thinking are highly valued, making it an exciting and impactful choice for the next generation of insurance professionals.
What developments do you see ahead for captives?
I expect the current hard market to persist, driving continued growth in captive formations and other alternative risk transfer mechanisms. As more organisations explore captives as a strategic risk management tool, I expect we will see increased innovation in programme structures and expanded use of captives beyond traditional lines. This growth will not only create more opportunities within the industry but also raise overall awareness of captives as a viable risk management solution across a multitude of industries.
Do you think your long-term future remains in the captives market?
The captives market has been a cornerstone of my career, providing both rewarding and challenging opportunities. I am excited to see how it continues to evolve in response to the complex challenges facing insurance today. Equally, I’m eager to see how HAI Group evolves to meet the ever-changing needs of the public and affordable housing sector. As a leading captive in this space, we are uniquely positioned to innovate and provide tailored solutions to help our members navigate risks effectively.
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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