Sandy Bigglestone is Deputy Commissioner of the Captive Insurance Division of the Vermont Department of Financial Regulation.  She is responsible for the administration and regulation of captive insurance companies and risk retention groups.

Having been with the Division since 1997, Sandy has a few decades of experience, and has had a successful career regulating captive insurance. She was appointed as Deputy Commissioner effective September 1, 2022, after serving as a principal staff member to her predecessor for 14 years.

Sandy is a Certified Public Accountant, Certified Financial Examiner, a Certified Public Manager with the State of Vermont, and earned an Associate Professional in Insurance Regulation designation from the National Association of Insurance Commissioners.

In 2018, Sandy was a recipient of the Women to Watch Award presented by Business Insurance for her leadership, expertise, and accomplishments in the captive insurance industry.

The 2024 Captive Review Power 50, which recognizes the most influential professionals in the global captive insurance industry, named Sandy at #1.

Also in 2024, Sandy was nominated and selected as one of the top 50 female leaders in the captive industry by Captive International.