Bigglestone to step down from Vermont DFR

The Vermont Department of Financial Regulation (DFR) has announced the retirement of Sandy Bigglestone (pictured), deputy commissioner of the Captive Insurance Division and one of the most respected leaders globally within the captive insurance industry. 

Bigglestone officially retires on January 1, 2026, concluding a distinguished career in state government that began in 1997 and helped solidify Vermont’s position as the internationally renowned domicile for captive insurance, the DFR said.

As Deputy Commissioner, Bigglestone led the administration and regulation of Vermont’s captive insurance companies and risk retention groups—an industry that has become a cornerstone of Vermont’s financial sector and a model of regulatory excellence worldwide. 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 said. “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 has served in the Department for nearly 30 years, and her contributions and leadership have earned her numerous industry accolades. In 2018, she received the Women to Watch Award from Business Insurance for her professional achievements and impact on the captive insurance sector. In both the 2024 and 2025 Captive Review Power 50, Bigglestone was ranked #1, distinguishing her as the most influential professional in the global captive insurance industry two years in a row. She was also named one of the Top 50 Female Leaders in Captive Insurance by Captive International in 2024.

Reflecting on her retirement, Bigglestone shared: “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.”

An announcement regarding transition plans and interim leadership will be released in the coming weeks, the DFR stated.

“Throughout her nearly three decades in the State government, Sandy Bigglestone has embodied excellence in public service and regulatory leadership,” said the DFR in a statement. “Her legacy will continue to shape Vermont’s captive insurance landscape for years to come.”

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