FORTY under 40: Brett Feldman
Brett Feldman, vice president of underwriting for health solutions, Captive Resources.
Brett Feldman has an extensive background in insurance underwriting, captive operations and financial services. Early in his career, he held various roles in financial operations and investment banking. In 2013, he joined Ironshore Insurance, where he developed his expertise in underwriting across multiple divisions. In 2020, he moved to Berkley Accident and Health as regional underwriting manager, later being made director of captive underwriting, charged with expanding the company’s captive insurance portfolio.
In 2023, he joined Captive Resources as vice president of underwriting for health solutions. He leads strategic initiatives to expand its underwriting capabilities in the captive insurance market. He also develops relationships with fronting carrier partners and manages production underwriting, clinical risk management and underwriting operations.
Over the course of his career, he has developed and managed a spectrum of captive insurance solutions, enabling companies to reduce risk and control costs by creating member-owned group captives, and has cultivated a deep understanding of the intersection of insurance and risk management strategies.
I'm passionate about developing the captive insurance industry’s next generation of leaders and delivering best-in-class service
How did you first become involved in captive insurance?
First while working for a medical stop loss managing general underwriter who assumed underwriting risk through a captive. However, my most impactful experience with member-owned captives resulted from one of the best career decisions I ever made – choosing a lower-level role in medical stop-loss captives over a more senior position in traditional stop-loss.
At the time, group captives were gaining traction in this market. I was both intrigued by the model and confident it represented the industry's future. In that first role, I led a team of underwriters and analysts, overseeing new and renewal underwriting for 14 group captives of varying sizes and profiles. It was exciting and rewarding, working alongside actuarial, operations, distribution partners and policyholders – all with a shared commitment to implementing best practices and driving success in the captive space.
What are the greatest challenges of working in this industry, and what do you find most rewarding?
The demand for talent in our market far exceeds the supply, creating significant opportunities for the next generation and for organisations committed to developing new leaders. Rising healthcare costs, driven by the increasing frequency and severity of high-cost treatments, present ongoing risk management challenges that require innovative solutions.
The most fulfilling part of my work is our positive impact in the marketplace. Helping employer groups take ownership of their data and gain control over their medical benefits spending is incredibly rewarding. Beyond that, I’m grateful to work with such an exceptional team. The support I receive from Captive Resources is second to none – I’m surrounded by industry veterans who are always willing to share their knowledge, making it an inspiring and collaborative environment.
Would you recommend the captive insurance industry to young people as a future career path?
Absolutely! This industry is poised for continued growth and will strongly demand young talent. If I graduated today, I’d seek out a reputable company in the captive market as the ideal place to start and build a rewarding career.
What developments do you see ahead for captives?
I anticipate this market will keep expanding as companies increasingly seek to take control of their data and manage their largest and continuously rising expenses.
Emerging technology is set to impact the captive insurance market significantly, driving efficiency, enhancing risk management and unlocking new growth opportunities.
Do you think your long-term future remains in the captives market?
I certainly do. I'm passionate about developing the captive insurance industry’s next generation of leaders and delivering best-in-class service to our partners and member-companies. I’m committed to this work for the long haul and fully intend to make this the industry I retire from.
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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