Why Vermont Is Becoming the Ultimate Launchpad for Captive Insurance Talent

As the hub of captive insurance in the U.S., Vermont abounds with career opportunities.

By: Elisa Ludwig | July 12, 2025

Topics: Captives | Jul./Aug. 2025 Issue

Captive insurance is surging — experts project that the market will top $250 billion by 2028 — and the boom is generating cost savings, spurring innovation and creating jobs. Nowhere is this more true than in Vermont, largely regarded as the nation’s hub of captive insurance — and now the frontier of a strong job market. Vermont has been licensing and regulating captive insurance companies since 1981. While not the first state in the U.S. to domicile captives, it became an early leader.

In 2024 alone, Vermont welcomed 41 new companies, making 683 total licensed captives in the state. “Vermont recognized the importance of this industry on our economy and its potential to generate jobs and tax revenue,” said Brittany Nevins, captive insurance director for the state’s Department of Financial Regulation.

“The result is that we have devoted a great deal of resources into building an infrastructure in Vermont to support the industry, with captive managers, investment bankers, attorneys and other professionals all located here.”

Nevins’ department employs 32 regulators exclusively devoted to captive insurance — the largest of any regulatory department in the world.

With the Vermont Captive Insurance Association (VCIA) headquartered in the state and actively working to modernize state and federal statutes to reflect the needs of the evolving industry, Vermont has developed a reputation as a regulatory pioneer, willing to proactively pivot as needed to drive the industry forward.

Help Wanted

In recent years, the steady growth of captive insurers has created a demand for a larger workforce. In 2022, the state’s Department of Economic Development partnered with VCIA to launch the Vermont Captive Insurance Emerging Leaders (VCIEL), an initiative to help educate young professionals about the field and its potential career paths in the nation’s top domicile.

At the Department of Financial Regulation, recruitment is ongoing for new hires — particularly those with accounting, management, legal or actuarial expertise. Many recently-hired regulators come from the industry side, Nevins said, whether that’s captive insurance specifically or the insurance field in general, bringing their expertise from the private sector to government work.

“There is a need for personnel in the front office who run licensing and respond to inquiries and requests from insurers, and then we have a dedicated part of the team in the field examination office for the ongoing examination and analysis that’s required under the National Insurance Association,” said Dylan Moss, insurance examiner-in-charge of the Department of Financial Regulation, Vermont.

The Next Generation in Captive Insurance

Native Vermonter Richard Wells was first educated about the captive industry while studying accounting at Champlain College. A captive manager came to speak to his class, and the talk resonated with him: He saw a career field that could open a world of opportunity, all from within the state limits.

“Upon graduation, I knew I wanted to stay local, but I also wanted the chance to build a dynamic career,” he said. “Straight out of college, I joined a captive manager and worked there for 16 years.” Wells was hired by the Department of Financial Regulation about two years ago.

He has enjoyed the more predictable rhythms of the public sector job and more time at home with his family. At the same time, the job is challenging, requiring critical thinking on a daily basis as well as regular professional training to keep him up to speed on industry trends.

In the time he has been with the department, he has been steadily promoted from examiner to examiner-in-charge to assistant chief examiner. For her part, financial examiner Catherine Reimer came to the department about 18 months ago from a 25-year career in corporate America.

“After I finished my degree in actuarial science, I worked in risk management, and then for the last many years, I served in the investment management division of an insurance company,” she said.

“When my child graduated from high school, I took some time off to consider my next steps, and I ended up moving from Atlanta, Georgia to Vermont.”

While in Vermont, Reimer learned more about the captive side of the industry. When the examiner job opportunity presented itself, she was intrigued — especially about the chance to push herself and learn new things on a regular basis at this stage in her career.

“In a way I am going back to the early part of my career while I use my risk management background,” Reimer said.

“At the same time, I am looking at companies and figuring out how to add value as a regulator. The fact that the work is different every day is very enticing to me. There’s a very positive relationship between the companies and regulators, and that makes the work environment productive.”

There’s an added benefit, Reimer added, to being situated in the nerve center of the industry and going to the VCA conference each year and expanding her network of professionals in the field.

Making an Industry-wide Impact

At the Department of Financial Regulation, examiners are not just holding companies accountable to regulation but also collaboratively working with them to build a sustainable industry that serves all stakeholders — there’s a real sense of contributing to a growing field and leaving a positive mark.

“What we do is unique in that it’s less focused on financial results year to year and more focused on a holistic picture of emerging or prospective risks for the entire company as related to operational or strategic oversight,” Moss said.

The risk-based approach, he said, allows the team to be more focused and streamlined, identifying risks unique and specific to each company, and tailoring regulation accordingly. The goal is to make the process more efficient for everyone.

Priming the Pipeline

Yet even as opportunities steadily grow in Vermont, it remains challenging to fill all of the available job openings. One major reason is a general lack of awareness about the insurance industry and the captive slice of that in particular.

“I don’t think anyone necessarily plans to work in insurance as a college student,” Moss said.

He recommended that high school or college students pursue internships to learn more about the field firsthand: “Not only are there many fairly well-paying jobs with good companies here but these are jobs where you can stay in a small town in Vermont, while having access to high-level corporate leaders around the world.”

Like his colleagues, Wells has a vested interest in keeping the industry booming in his home state and continuing the cycle for future generations. “We will do everything we can to remain the gold standard,” Wells said.

“As Vermonters, we want to see this work and these jobs stay here.” And truly, with year-over-year growth for the past five years, the growth of captive formation in Vermont shows no sign of slowing down.

“The industry is naturally growing, new captives are consistently forming, and we’re solving problems in ways that benefit people every day,” Nevins said. “It’s very simple. If we want to continue on this path the workforce needs to keep pace.” &

Elisa Ludwig is a contract writer based outside Philadelphia. She has written extensively about cybersecurity issues for the Junto blog on the eRiskHub. She can be reached at [email protected].

New Ways of Working

Dan Mogelnicki, Senior Vice President and Professional Liability Product Leader, Westfield Specialty

The shift toward remote and hybrid work arrangements is creating new professional liability exposures, particularly affecting younger workers who are missing out on crucial face-to-face training opportunities.

“Professional liability exposures come from two bases: knowledge based, and execution based,” Mogelnicki explains. The reduced collaboration inherent in remote work mirrors challenges experienced in education when the Covid pandemic pushed students into taking their classes remotely.

“The learning was not the same,” Mogelnicki said.

“There was an inability to interact, a lack of training, and a diminished ability to communicate and collaborate,” he said.

Artificial intelligence usage presents another emerging exposure area. While carriers have experienced only a handful of AI-related miscellaneous professional liability claims to date, industry experts anticipate that the number of claims in this area is going to grow.

“We know that these will increase tremendously over the next months and years,” Mogelnicki states, though no significant settlements have emerged yet from this developing risk area.

Unlike some other liability coverage areas, such as casualty, miscellaneous professional liability is relatively insulated from nuclear verdicts. Mogelnicki explains that most nuclear verdicts involve bodily injury components found in products liability, auto liability, medical malpractice, and architects and engineers professional coverage, while miscellaneous professional liability claims typically address pecuniary or economic losses.

However, exceptions exist where policies include contingent bodily injury or property damage coverage. Real estate property managers represent the primary example, where failure to perform duties can result in bodily injury claims that potentially invite larger verdicts.

Like any line of insurance, MPL faces increasing loss frequency due to evolving societal expectations that are leading to more frequent and potentially expensive legal actions.

“There’s an assumption that no one ever makes a mistake, and if something bad happens, people feel entitled to a huge amount of compensation,” Mogelnicki explains. This trend reflects broader cultural shifts that are affecting professional services exposures.

The remote work dynamic compounds these challenges by reducing organic learning opportunities.

Mogelnicki illustrates this with a personal example of an early-career underwriter who spontaneously asked a crucial question during a casual office encounter. “If we were not in the same place, he may never have asked me that question,” he notes.

Virtual meetings, on the other hand, often have a chilling effect on questions due to technical limitations and social dynamics, leading professionals to make potentially problematic assumptions.

Communication and Quick Turnaround

In response to these evolving challenges, leading carriers are emphasizing personalized service and rapid response times.

Westfield Specialty differentiates itself through direct broker communication and problem-solving approaches rather than standardized procedures. ” We have conversations with our brokers to gain an understanding of the risks they are trying to find solutions for,” Mogelnicki emphasizes. “We don’t have a cookie cutter approach.”

The company’s service model prioritizes quick turnaround times, with the majority of submissions receiving quotes within 24 hours. “We’ve built a timely review process that enables a very quick turn around on a large majority of the risks that are submitted,” Mogelnicki said.

“Challenging or complex exposures are going to take a little bit more time, but we’re happy to work with brokers to place such risks,” he said.

This approach extends beyond speed to encompass creative coverage solutions addressing unique broker and client needs. “We strive to be the solution for the challenging situations that our broker customers face,” Mogelnicki states. The strategy focuses on providing comprehensive coverage at fair prices while maintaining flexibility for non-standard risks.

A combination of responsive service, creative problem-solving, and competitive pricing puts Westfield Specialty in a good position to address the evolving miscellaneous professional liability landscape effectively. As new exposures from the use of AI and remote work arrangements continue to develop, carriers emphasizing adaptability and broker relationships appear best positioned to navigate these emerging challenges.

To learn more, please visit https://www.westfieldspecialty.com/.

This article was produced by the R&I Brand Studio, a unit of the advertising department of Risk & Insurance, in collaboration with Westfield Specialty. The editorial staff of Risk & Insurance had no role in its preparation.

Westfield Specialty is a prominent specialty insurance carrier, leveraging the financial strength of Westfield, a leading U.S.-based property and casualty insurance company and the well-established Lloyd’s of London Syndicate 1200. Westfield Specialty currently underwrites in the U.S., U.K., and Dubai, and has 400 employees globally. Our experienced team brings deep expertise to the specialty market and offers unique insurance solutions for specialized risks that helps protect businesses, recover losses, and assist in driving growth for clients.