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2018 Women to Watch: Sandy Bigglestone

Sandy Bigglestone
Director of captive insurance
Vermont Department of Financial Regulation
Montpelier, Vermont
Age: 49

For Sandy Bigglestone, no job could be more satisfying than her position as a top captive insurance company regulator in Vermont.

“This is an industry that always is evolving. There is always something going on and something to learn,” said Ms. Bigglestone, director of captive insurance with the Vermont Department of Financial Regulation, which regulates nearly 600 captives in the world’s third-largest domicile.

Those who work with her say Ms. Bigglestone’s passion to learn has played a key role in Vermont’s captive growth.

“Her hard work and dedication have been critical in our success as a domicile,” said Christine Brown, the department’s assistant director of captives in Montpelier, Vermont.

Others applaud her openness to new ideas. “She is not only incredibly knowledgeable, but also is an incredible listener,” said Richard Smith, president of the Vermont Captive Insurance Association in Burlington.

“She always approaches issues with an open mind,” concurred David Provost, Vermont’s deputy commissioner of captive insurance in Montpelier.

Because of her great knowledge of the captive industry, Ms. Bigglestone has been able to maintain strong relationships with state legislators, Mr. Smith said.

In 1997, Ms. Bigglestone joined Vermont’s captive department as an examiner after working for a public accounting firm. “I had heard about the Vermont captive insurance industry, and I was very intrigued. Why were captives such a big industry? So when there was a job opening, I applied,” she recalled.

From that beginning, Ms. Bigglestone has loved being a captive regulator. “I have not been bored one single day because the captive industry always is evolving,” she said.

She was named chief captive examiner in 2004 and was promoted to her current position in 2010. While many regulators are glued to their desks, Ms. Bigglestone is just the opposite. “I enjoy being out of the office and being accessible,” she said.

She is a frequent speaker at captive conferences, which she said gives her the opportunity to meet people in the field, as well as boosting her knowledge of issues.

Married with two children, she said she also “loves being outdoors. I hike, ski and mountain bike.”

NEXT: Nina Boone
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