Sandy Bigglestone

Ms. Bigglestone is managing director and chief governance, regulatory, and compliance officer at Strategic Risk Solutions. Until her retirement at the end of 2025, she served as the deputy commissioner of captive insurance for the Vermont Department of Financial Regulation (DFR) after having served with the Captive Division since 1997. She also served as acting commissioner of the DFR in early 2025. Prior to her regulatory career, Ms. Bigglestone provided audit and tax services for clients of a public accounting firm and was employed as an accountant in a Vermont medical center. Ms. Bigglestone is a Certified Public Accountant and Certified Financial Examiner and received a Certified Public Manager designation from the State of Vermont for her participation in a state government leadership career development program. Ms. Bigglestone also earned her Associate Professional in Insurance Regulation designation from the National Association of Insurance Commissioners.