Sandy Bigglestone Receives VCIA Industry Service Award

Sandy Bigglestone received the Vermont Captive Insurance Association's (VCIA's) 2026 Industry Service Award in recognition of her contributions to the captive insurance industry and Vermont's captive insurance community.

The award is selected annually by the VCIA Board of Directors and recognizes a member whose support and contributions have strengthened the captive insurance industry and advanced its general welfare.

Ms. Bigglestone recently moved from state government to the private sector after 30 years with the Vermont Department of Financial Regulation (DFR). During her tenure, she helped shape Vermont's captive regulatory environment and represented the state and the captive insurance industry in national regulatory and policy discussions through her work with the National Association of Insurance Commissioners.

In accepting the award, Ms. Bigglestone recalled that her first week at the Vermont DFR coincided with the VCIA conference. Vermont had approximately 270 active captives at the time, and the department registered her for the event so she could meet industry participants and learn about the captive sector.

"I fell in love," Ms. Bigglestone said. "I am truly honored, deeply honored, and humbled to receive this VCIA Industry Service Award."

Ms. Bigglestone emphasized that her contributions were possible because of the people with whom she worked throughout her career.

"No one accomplishes that alone," she said. "Whatever contributions I have made over the years have only been possible because of the remarkable people I've had the privilege to work alongside."

Reflecting on her career, Ms. Bigglestone described "progress with purpose" as a central theme. She said progress requires professionals to acknowledge what they do not know, continue learning from others, and engage in meaningful discussions about new challenges.

"No matter how much experience you have, someone will always find a way to ask you a question you've never heard before," Ms. Bigglestone said.

She also reflected on the captive insurance industry's continued evolution and the range of professionals who contributed to Vermont's development as a captive domicile, including regulators, legislators, captive owners, managers, attorneys, auditors, actuaries, and other service providers.

Ms. Bigglestone said Vermont's success was not attributable to one person or organization, but to a community that values "expertise, transparency, integrity, and mutual respect." She also thanked her past and present colleagues, saying their dedication and professionalism made her both a better regulator and a better person.

"I'm proud of what we have accomplished together, and I remain optimistic about the future of the captive insurance industry and the people who will continue to lead it forward," Ms. Bigglestone said.

During the awards presentation, VCIA also presented its Gold Standard Award to Tracy Hassett in recognition of her service, volunteerism, and support of the association. Diane Leach was named an honorary member, VCIA's highest recognition, following 4 decades of service to the organization.