Vermont’s Blueprint for Succession Planning Success

Following the recent announcement of Sandy Bigglestone’s transition to Deputy Commissioner, the Government’s Captive Insurance Division is sharing some of the secrets of its 40-year long history with its loyal and long-standing team.

Succession planning should be at the heart of any successful business or organization.

It is important to establish a plan to ensure the organization’s long-term sustainability, and to avoid shocks or sudden changes.

But in the captive insurance industry, succession planning is more difficult than in many other sectors.

The Baby Boomer generation that started the business in the 1980s is retiring and there aren’t enough new professionals coming into the industry to fill the need. This problem has been exacerbated by the COVID-19 pandemic and the Great Recession of 2021.

Vermont, however, is a great example of a home that is fighting the trend and making plans for others to follow. With a track record of 40 years, the government’s Captive Insurance Division has been promoting from within as much as possible and the longevity of its employees is reflected in its low interest rates.

Sandy Bigglestone, Director of Bonded Insurance, DFR

The Division’s succession planning has been highlighted by the recently announced transfer of Director of Captive Insurance, Sandy Bigglestone, to Deputy Commissioner. With Dave Provost stepping down this summer, Bigglestone, who has been with the Division since 1997 and, hired Provost in 2001, will step in to replace him.

It’s a move that’s been in the works for a while, with the two working together and Bigglestone having mastered his craft over the past 14 years. Having started as a successful entrance exam examiner, she also has a deep understanding of the demands of her relationship with the National Association of Insurance Commissioners and its accreditation program, as well as legislative and budget processes.

“Next-day planning has to be a constant mindset,” Bigglestone said. “Organizations need to look at their leadership pipeline and make sure they have a plan in place when the time comes for the person at the top to move on.”

“In Vermont’s case, continued improvement is very important to the companies we work with. It is a testament to our satisfaction in our work that many of our executives have been in senior positions for so long.”

“Our team has enough strength and wants to help make the project successful. This kind of commitment will ensure that we move forward. “

Planning is Important

Instead of reacting when people quit or resign, organizations need to be proactive and plan for the future. This requires building the infrastructure necessary to attract and retain more talent on an ongoing basis.

Succession planning also brings a number of financial benefits. Captive companies raise the local economy through taxes and fees, which are used to support and employ local people. In Vermont’s case there are about 400 Vermonters directly employed in the sector, according to a 2019 survey.

There is also a big downside no implementing succession planning. Failure to do so means that valuable knowledge and experiences are lost.

“There’s a big price to pay for not having a succession plan,” Provost said. “That’s why it’s important to have people on all career paths who are ready to step up when the time comes.”

Image Editing

Dave Provost, Deputy Commissioner, Captive Insurance Division, DFR

The biggest problem with recruiting in the industry, however, is seeing the insurance industry as a suit salesman. To solve this problem, organizations need to do more in the crowd and dispel this myth by selling all available services.

“We have to make it known that it’s not for sale,” Provost said. “There are other very interesting tasks that people don’t immediately think about, such as data analysis, security and loss management.

“Also, the work is very interesting and varied. In what other business can you get to talk to people about what they earn and get a unique insight into how their business works? Each company is different from the next.”

These career options should be encouraged by establishing strong connections with colleges and universities, and attending career fairs and providing scholarships to students. These companies should also be running more campaigns and education in more areas, as well as using the media to raise awareness of the opportunities available.

Vermont’s Captive Insurance Division recruits workers every summer and directly affects them in its work. They also attend the annual meeting of the Vermont Captive Insurance Association, where they network, learn from educational programs and see their companies.

The department, in conjunction with the Department of Economic Development, has also launched a new careers page on its website ( which has many resources for people to learn more about captive industries like career choice. In addition, it has run a number of blogs and videos focusing on some of the new professionals who have joined, and their job satisfaction and benefits.

“A big part of the education is just sharing some of the success stories of people in the industry,” said Brittany Nevins, Director of Vermont Financial Insurance. “We have been explaining all the benefits of working in captive companies, such as an average salary of $91,000 per year, and the opportunity to travel, and gain experience in many types of businesses and sectors. Especially in Vermont, in rural areas, it is not difficult to find all these benefits in any other sector.

Adaptive Quality

Brittany Nevins, Director of Insurance Financial Development, State of Vermont

Flexibility and other selling points. The Captive Insurance Division had already planned to work remotely before the pandemic, which allowed them to attract more employees.

In terms of education, the Division runs a program to improve existing skills and develop new ones. It also fosters a culture that attracts critical thinkers and problem solvers, and looks to support people in their personal growth and professional development, and provide new opportunities for those who want them.

“We want to give people the opportunity to stretch their talents to reach their full potential,” Bigglestone said. “For example, if someone leaves an important meeting, I want to be confident that someone else will step in. It may be important to improve the succession process in the future by making sure that others are ready to take on roles and responsibilities. .”

Another important part of the equation is diversity and inclusion. Vermont provides its employees with specialized training in this area, and some employees are part of industry initiatives such as the Captive Insurance Companies Association’s Amplify Women™ and NextGen committees.

“These initiatives help increase the opportunity for people to have their voices heard and be recognized for their work in the industry by being nominated for an award,” said Nevins. “They are also helping groups that were previously underrepresented to do their work by giving them opportunities for social interaction and communication. These activities help to appreciate succession planning and companies and organizations should encourage their employees to participate if possible.”

To learn more about Vermont’s Captive Insurance Division and industry opportunities, visit



This article was created by R&I Brand Studio, part of the Risk & Insurance Marketing Department, in partnership with the State of Vermont. The authors of Risk & Insurance had no part in the preparation.

The State of Vermont, known as the “Gold Standard” for captives, is the nation’s leading insurer, with more than 1,200 licensed insurance companies, including 48 of the Fortune 100 and 18 of the Dow 30 companies.