Sandy Bigglestone, deputy commissioner of captive insurance in the Vermont Department of Financial Regulation, has announced her intention to step down on Jan. 1, 2026.
Bigglestone has served in the captive insurance department for nearly 30 years, and her contributions and leadership have earned her numerous industry accolades. In both the 2024 and 2025, she was ranked atop the Captive Review Power 50, distinguishing her as the most influential professional in her field for two years in a row. She was also named one of the Top 50 Female Leaders in Captive Insurance by Captive International in 2024.
“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 also influenced the captive insurance industry around the world. We thank her for her extraordinary service and congratulate her on a remarkable career.”