Vermont's Top Captive Insurance Regulator to Retire in January

Sandy Bigglestone, deputy commissioner of the Vermont Department of Financial Regulation (DFR) Captive Insurance Division, will retire on January 1, 2026, after nearly 3 decades in public service. Her retirement marks the end of a career that helped define Vermont's role as a global leader in captive insurance regulation.

Ms. Bigglestone joined the department in 1997 and rose through the ranks to oversee the state's captive insurance companies and risk retention groups. As deputy commissioner, she led the development of regulatory frameworks that positioned Vermont as the leading US domicile for captives, known for its balance of innovation and strict oversight.

"Sandy's leadership has been instrumental in sustaining Vermont's global reputation as the gold standard for captive insurance regulation," DFR Commissioner Kaj Samsom said. "Her expertise, professionalism, and commitment to integrity have not only shaped the Department but have influenced the captive insurance industry around the world."

Ms. Bigglestone's impact has been recognized across the industry. In 2018, she received the Women to Watch Award from Business Insurance. Captive Review ranked her #1 in both the 2024 and 2025 editions of its Power 50 list, identifying her as the most influential figure in the global captive insurance industry. In 2024, Captive International named her one of the Top 50 Female Leaders in Captive Insurance.

Reflecting on her time in office, Ms. Bigglestone said, "It has been an honor to serve the State of Vermont and to work alongside such a dedicated and knowledgeable team. Also, the captive insurance community is filled with exceptional people, and I'm grateful to have spent my regulatory career contributing to an industry that values innovation, collaboration, and integrity. I am incredibly proud of what we have built together for Vermont."

DFR will release details regarding transition plans and interim leadership in the coming weeks.