The Vermont Department of Financial Regulation (DFR) announces the retirement of Sandy Bigglestone, deputy commissioner of the Captive Insurance Division, effective 1 January 2026. Bigglestone retires after nearly 30 years of service in state government, having joined the department in 1997. Her tenure has been instrumental in solidifying Vermont's position as a leading international domicile for captive insurance. As deputy commissioner, Bigglestone led the administration and regulation of Vermont's captive insurance companies and risk retention groups. Under her leadership, the division earned a reputation for robust oversight, responsive regulation, and a collaborative approach that balanced industry innovation with strong solvency protections. "Sandy's leadership has been instrumental in sustaining Vermont's global reputation as the gold standard for captive insurance regulation," DFR Commissioner Kaj Samsom says. "Her expertise, professionalism, and commitment to integrity have not only shaped the department but have influenced the captive insurance industry around the world. We thank her for her extraordinary service and congratulate her on a remarkable career." Bigglestone's contributions and leadership have earned her numerous industry accolades throughout her career, including recognition for her professional achievements and impact on the captive insurance sector. Reflecting on her retirement, Bigglestone says: "It has been an honour 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." The DFR says an announcement regarding transition plans and interim leadership will be released in the coming weeks. Vermont's captive insurance industry has become a cornerstone of the state's financial sector and a model of regulatory excellence worldwide.
