FORTY under 40: Caleb Love
Caleb Love, senior adviser, GPW and Associates.
Caleb Love first encountered the captive insurance industry when an intern with Johnson Lambert, an audit firm specialising in insurance. He was intrigued by the captive clients he worked for and, when offered a job, readily accepted.
After two years working on all types of captive audits, he moved into captive management with Willis Towers Watson, where a passion for captive insurance blossomed under the wing of several mentors, and he was quickly managing a diverse portfolio.
As this grew, he became known for innovation in leveraging existing tools more effectively and efficiently and integrating new technology into the tech stack. After three years, a former mentor offered him the chance to see a different slice of the industry, and he joined GPW and Associates as a senior adviser to its group captive practice. His role includes managing group captives and serving as a resource on captive formations and feasibility studies as well as advising on operations for single-parent captives.
How did you first become involved in captive insurance?
Through an internship while in graduate school, where the programme director heavily encouraged an internship during the spring semester. All the interviews were in the fall, less than a month after, I moved to Vermont. I wasn’t sold on being in Vermont long term, but the programme director insisted I’d thank her later. She even went as far as sketching a map to get me to the interview on time as GPS sometimes wasn’t clear on the office location.
The most rewarding aspect is the meaningful impact you can have on your clients. Every day presents a new opportunity to make a real difference
What are the greatest challenges of working in this industry, and what do you find most rewarding?
I feel it is staying organised while managing the pressure of tight deadlines. Unlike traditional accountants, who focus on a single company, a captive manager may be responsible for overseeing a dozen different captives. Finding an organisational system that works for you is essential. While some prefer using Excel trackers, there are numerous platforms available to help streamline workflows and manage deadlines effectively.
The most rewarding aspect is the meaningful impact you can have on your clients – an impact that often extends to the broader public. This can take many forms, whether collaborating with a client and actuary to insure a risk the commercial market won’t cover or with a captive on medical stop loss cost containment measures that help keep employees’ health insurance premiums affordable. Every day presents a new opportunity to make a real difference.
Would you recommend the captive insurance industry to young people as a future career path?
Absolutely! My advice is to seek an internship, build your industry knowledge and continually seek new challenges and opportunities to innovate.
What developments do you see ahead for captives?
I see a real opportunity for companies to use their captives to keep health insurance premiums low while providing top-notch benefits to their employees. As the cost of care rises, I think captives could become pivotal in this space.
Do you think your long-term future remains in the captives market?
I certainly do. I can’t wait to see what the future brings!
Click here to read Captive International’s third FORTY Under 40 2025 publication.
Did you get value from this story? Sign up to our free daily newsletters and get stories like this sent straight to your inbox.
