Vermont’s Deep Leadership Bench: Why Depth of Expertise Gives Captive Owners Confidence

Vermont's experienced captive insurance division maintains its global leadership through collaborative regulation, continuous innovation, and strong partnerships with both the industry and state lawmakers.

By: Bruce Shutan | July 10, 2026

If the Vermont Department of Financial Regulation’s captive insurance division could be compared to a professional sports franchise, you might think of the Los Angeles Dodgers, located nearly 2,400 miles away.

Both organizations field what insiders consider to be the deepest benches of talent relative to competitors in their respective areas of expertise. They feature a lineup of professionals who helped establish and maintain a standard of excellence.

The captive insurance division’s 32-member staff boasts more than 300 years of combined regulatory experience and north of 500 years of combined industry experience. That includes seven certified public accountants and 13 accredited or certified financial examiners.

Every member of the leadership team – deputy commissioner Christine Brown, assistant director Jim DeVoe-Talluto, director of examinations Dan Petterson and chief examiner Heidi Rabtoy – has nearly or more than 20 years of experience in the department.

While each of the three previous leaders – Len Crouse, David Provost, and most recently, Sandy Bigglestone – had their own style, the division’s culture has been maintained, even strengthened.

Unpacking Teamwork

It is at once collaborative and team-oriented, according to Rabtoy, who said that also happens to be the nature of captives themselves. As captive operations become more innovative and complex, she said there’s a pressing need for the division to work closely as a team to address market challenges and determine how best to regulate alternative risk transfer arrangements.

“What we’re recognizing is there’s a lot of institutional knowledge that needs to get passed down to staff,” she notes, “but that there’s also a lot of great knowledge being brought from our newer staff in regards on how can we do things better, innovate, be more efficient, and add value to our stakeholders and department as a whole.”

What sets the division apart from captive regulators in other states who are trying to emulate Vermont is simple, Brown explains. It’s about deploying a deep bench of staffers who are willing to understand and scrutinize the companies they regulate on a granular level from the very beginning. That thorough vetting includes an annual analysis and a larger examination every five years to address various touch points.

Dan Petterson, director of examinations, captive insurance division, Vermont Department of Financial Regulation

The division does about 100 examinations a year. “When you do that many examinations, you tend to build up quite a library of information,” Petterson said. Rabtoy said exams are valuable not only because they help the division understand how operations are going and ensure that best practices are followed, but also provide value to the captives.

“We’re all aspiring for the same goal, which is to make sure that the captive is successful, and we feel the best way to do that is being able to talk to companies not only about how well they’re doing, but if things aren’t going so great as well,” Brown said. “It’s helpful to know so that we can try to help steer them out of whatever trouble they might be heading towards.”

A multi-talented roster of professionals with expertise and longevity are credited with offering the kind of stability and continuity across 45 years that gives captives owners confidence in choosing to domicile their captive in Vermont. Many staffers have worked alongside or under each of the three leaders who served before Brown took charge.

Brown is fully aware of the delicate balance between regulating the captive industry and attracting business to her state, but it’s also a symbiotic relationship. Rabtoy believes that as regulators, the Vermont team is firm but fair.

“We want to make sure that we’re modeling regulation that we think is prudent and responsible,” she said. “It’s a little tricky as a regulator having this competition that you have to think about in addition to regulation. Usually those things don’t mesh, but in the captive industry they do. That’s why we’re always mindful about what’s setting us apart, what value are we adding and where should we be deploying our resources to make sure that we’re still staying on top of people’s minds.”

The division arranges meetings with service providers as well, serving as a helpful resource to add more value where all parties benefit from an open dialogue.

When Brown and her colleagues engage with captive owners and managers, the mission is to help them achieve the best possible outcome. “We are here to provide the support and oversight for the best chance of success, and I think that concept extends to how we engage with state government and our legislative partners,” DeVoe-Talluto said, noting the importance of consensus-building.

Petterson considers all of the relationships the division builds with companies and service providers to be the backbone of what has turned the Green Mountain State into the nation’s most popular domicile for captives.

The same is true internally. Any time there are board meetings or new-license meetings, the goal is to have at least a few of the division’s leaders involved to ensure good succession planning, Brown said. In fact, Rabtoy notes that this issue has been a significant part of her own role almost on a daily basis and top priority under Brown’s leadership.

Developing Fresh Eyes

The synergy of experienced leaders with institutional memory working alongside newer hires with a fresh perspective allows the division to move forward without getting stuck.

“We’re always trying to look for improvement and make sure that what we do makes sense for us and outside stakeholders as well,” Brown said.

Staff standouts include Jenn Kerner, assistant chief examiner who has been with the division for about 20 years, as well as Richie Wells and Brianne Orisko, both of whom share that same title but are newer to the department, and Amber Walsh, a captive insurance analyst for the past 15 years. Others include insurance examiners Peter Wernhoff, Dylan Moss and Catherine Reimer.

DeVoe-Talluto lauds Wells and Orisko for public accounting, auditing and captive expertise that brings a high-level perspective and bolsters the integrity of financial statements.

“While many of us have certain degrees of experience in management and CPA work, they really bring an incredible depth of experience that has enabled us to fine-tune our scope based on the valuable feedback they provide,” he said.

One of several unique aspects to this teamwork is there are through lines of leadership, education, training, internal learning and growth.

“We’re working with phenomenal young individuals who are bringing us diverse skill sets,” DeVoe-Talluto notes. Most of them have worked under the previous leadership, which spanned nearly 30 years, and he’s confident that they’ll carry forth a long history of innovation.

Brown said the division values professional development, and as such, builds in enough time to help staffers pursue various industry designations. “It is something we take very seriously because we know that it pays in the long run to have staff contribute in ways that they might not otherwise contribute,” she adds.

Seeding Innovation

When Vermont’s then-governor Richard Snelling signed the Special Insurer Act of 1981, DeVoe-Talluto said it laid the groundwork for a commitment to understanding why captives were being formed and offering those operators an opportunity to adapt and grow their programs.

Heidi Rabtoy, chief examiner, captive insurance division, Vermont Department of Financial Regulation

“We’ve seen companies develop much more complex captive programs over the years,” he observes, “and at each step along the way, we will understand and respond to their needs.”

That led Vermont to become one of the first U.S. states to establish a domestic domicile for captive insurance companies. He describes the post-911 landscape as the division’s largest growth years because companies knew that their captive could help with the co-participation and deductible access to the Terrorism Risk Insurance Act program.

Vermont now has more than 704 active captive licenses, and when factoring in cell structures, that number swells to more than 1,000. “It was really only in the last several years that we became the global leader in terms of premium volume and number of captive entities,” he adds.

One of Vermont’s key advantages is its responsiveness. “People feel like they can pick up the phone and call us, whether it be a new license application or business plan change, or even just a question that they have for us, that we’re timely and do things at the speed of business and not hold things up with bureaucracy,” Brown notes.

She said that effort is coming into a clearer focus updates to the division’s IT systems. Petterson is leading the charge in attaining greater operational efficiencies.

Streamlining Workflow

Acknowledging that being part of a governmental entity can saddle processes, he cites some workflows in development to explore different technologies that that would make internal processes more efficient and interactions with business partners more integrated.

Plans are in the works to streamline exam deliverables, including making more efficient use of time devoted to more risk-focused examinations. In homing in on the needs of companies, Rabtoy said her team plans to back away from areas that are less helpful.

“What we were hearing from captive managers is that there’s value on both sides of the fence here in making improvements,” she said.

Not surprisingly, the use of artificial intelligence is also on the agenda in the form of a pilot program. “It was really cool to see how it worked,” Petterson said, “but it also shined a light on redeveloping our processes so that these tools can actually integrate much more seamlessly and provide more efficiencies, while maintaining confidentiality.”

In recent years, there has been some re-domestication activity from offshore to onshore for various reasons, according to Brown. Vermont is updating its processes to make re-domestication easier for companies.

“The landscape is certainly changing when we look at Europe and the proliferation of captive jurisdictions over there,” she observes. “It feels similar to the U.S. and growth in domiciles here.”

Extended-Cabinet Meetings

From a governmental point of view, it has been eye-opening for Brown to step into the deputy commissioner role. “I have been so impressed by the fact that we’re invited to meetings where we’re able to sit with the governor as part of what he calls his extended cabinet to hear about his initiatives,” she said. “We all give a report to the governor weekly on how our work is contributing to his mission and our own mission. So, there’s a lot of collaboration, even at that level.”

Vermont is unique in that anyone can walk into the state house, tour the building and not need an appointment, she explains. In a small state of roughly 650,000 residents, she considers that an advantage because it allows her team to accomplish statuatory updates quickly. There is also a broad awareness about the value that the captive industry brings to the state.

State lawmakers grasp that value and work willingly with Brown and her team. When division leaders testify before the legislature, DeVoe-Talluto said “they have the confidence that what we’re bringing to them matters, makes sense and is going to be good for all state constituencies in terms of economic development.”

Cementing Ambitions

Looking ahead, Rabtoy is focused on nurturing the division’s deep bench of talented individuals who will serve as the next generation of regulatory leaders and continue to build partnerships that ensure success for the companies they regulate.

The division needs to double down on its commitment to the kind of continuous improvement that’s required to meet the future needs of captive owners, notes DeVoe-Talluto.

“Captives serve a critical role in meaningful corporate governance and risk management,” he explains, “and I think what we provide as regulators is that framework that allows companies to succeed. I hope that even in the face of broadening global competition, which I would characterize as a somewhat friendly competition, each jurisdiction brings a little different perspective.”

Attracting and retaining qualified experts to the department is a top priority in its ability to maintain a standard of excellence for regulating captives, according to Brown.

Another goal is to ensure that her team is educating people more broadly. One such example is Vermont’s involvement with the National Association of Insurance Commissioners.

“The more people learn about captives, the more interested or skeptical they may be, and we need to make sure that we’re educating people about the fact that these are well-regulated insurance companies,”
she said. &

Bruce Shutan is a versatile freelance journalist who has written for nearly 140 publications, corporate entities and individuals over four decades. He specializes in writing about employee benefits, self-insurance and captive insurance trends, and also has ghostwritten independently published business books and memoirs.

Rethinking Risk: Why Self-Insured Retentions Are Gaining Ground for Complex Liability Risks

As product liability risks grow more complex, self-insured retentions (SIRs) can help qualified organizations reduce costs, expand insurance capacity and strengthen claims control.

By: The Hanover Insurance Group | July 1, 2026

A Shifting Liability Landscape

Product liability risks are entering a new phase of complexity. Pricing pressures remain front and center, even as segments of the market begin to moderate. Capacity continues to fluctuate, attachment points remain elevated and underwriting discipline has tightened across higher hazard general liability and excess and umbrella layers.

Recent data reflects that reality. While U.S. commercial insurance pricing trended downward throughout 2025, insureds with significant product liability exposures continue to face challenges in securing optimal placements. A 2025 industry survey shows that 86% of independent insurance agents report challenges with market access and product availability as insurance carriers adjust capacity and underwriting strategies, highlighting that access to coverage limits remains limited for many complex risks.

Beneath these conditions lies a deeper issue: escalating loss costs. Social inflation continues to drive severity, with U.S. liability claims increasing 57% over the past decade due to rising litigation and large jury verdicts. These trends are reshaping how carriers deploy capacity and how clients access coverage.

While the market shows signs of softening, the underlying cost dynamics remain unchanged. “In an environment shaped by inflation, supply chain disruption and litigation volatility, these pressures are not only influencing pricing but also reshaping how organizations think about risk ownership and financing structures,” said Seth Hollis, head of specialty general liability at The Hanover. “Borrowed capacity is only one part of the equation. Retained risk is increasingly becoming another.”

For larger, well-managed organizations, self-insured retentions (SIRs) can serve as a powerful strategic lever, improving cost control and supporting long-term program stability. This not only serves as a strong selling point for agents but also enables them to better position clients within a challenging market.

Aligning SIR Strategies to Product Liability Risk Profiles

Seth Hollis, Head of Specialty General Liability, The Hanover

Product liability presents a risk profile that often aligns well with retained risk strategies.

Many organizations experience a pattern of predictable, lower-severity claims, while more catastrophic losses remain infrequent but impactful. Traditional insurance structures tend to price toward those high-severity events, driving premium costs even when day-to-day loss activity remains manageable.

For organizations with the right financial and operational profile, this presents a risk management opportunity. “Retaining a more predictable layer of risk can improve efficiency and total cost of risk over time, particularly for companies with strong safety controls and claims oversight,” Hollis said. “These organizations typically combine financial strength with operational discipline, supported by consistent cash flow, credible claims data and a long-term view of risk financing.”

In practice, SIR strategies can take multiple forms depending on the organization’s goals and risk profile. For example, a manufacturer with more frequent, predictable claims may retain a defined layer of risk, while another manufacturer facing less frequent but more severe claims may use an SIR to manage volatility while preserving protection for catastrophic losses. Larger commercial accounts may also use SIRs to gain greater influence over claims management outcomes, using retention to more closely align financial and operational controls.

The key is intentionality. SIRs should be designed around a well-understood risk profile, not introduced as a default response to market pressure.

From a carrier perspective, SIR structures also introduce alignment. When insureds manage claims within their retention, they tend to focus on preventing losses, handling defense strategically, and resolving matters more quickly. This alignment can lead to more sustainable results across the account.

The Value Equation: Cost, Capacity and Control

SIRs are often associated with premium savings — and for good reason.

By assuming a portion of risk, insureds can reduce the amount of exposure transferred to the carrier, which typically results in lower upfront premium.

However, that shift also introduces greater financial responsibility. Losses within an SIR are funded directly by the insured and may not be subject to an aggregate cap, requiring organizations to maintain adequate reserves and be prepared to absorb multiple losses within a policy period.

For organizations equipped to manage that responsibility, the value of an SIR extends beyond immediate cost savings:

Improved access to capacity: SIR structures can make complex product liability risks more attractive to carriers, supporting greater willingness to deploy limits.
Enhanced program structure: Flexibility exists to tailor retention levels across different product lines within a general liability program, allowing organizations to align retained risk with their operations.
Long-term cost stability: Reducing fixed premium costs while retaining predictable losses can lead to a more stable total cost of risk over time.
Greater claims influence: Organizations gain more direct oversight of defense strategy, legal expenses and settlement decisions within the retention.

Amid ongoing economic uncertainty and litigation volatility, these benefits can help organizations achieve more consistent and predictable risk outcomes.

Claims Management: The Critical Differentiator

The effectiveness of an SIR program ultimately depends on claims execution.

Managing losses within a retention requires discipline, speed and coordination. “Organizations need the ability to respond quickly to incidents, engage legal resources effectively and resolve claims before costs escalate.” Hollis said. This requires dedicated internal risk management leadership or strong alignment with third-party administrators, supported by clearly defined escalation protocols for more complex claims. A consistent legal strategy, backed by experienced counsel, plays a critical role in maintaining control over outcomes, while ongoing monitoring of claim trends helps ensure that lessons learned are continuously applied.

Even above the retention, carrier expertise remains essential. It provides loss analytics, benchmarking insights and strategic guidance that support the retained layer, help protect excess policies and drive a lower total cost of risk over time.

When these elements are aligned, SIR programs can perform as intended — improving outcomes at both the primary and excess layers.

Guiding the Client Conversation

For independent insurance agents and brokers, SIRs represent an opportunity to elevate the conversation around risk management for the right clients.

The most effective discussions move from “taking on more risk” to focusing on structuring risk more strategically. This includes aligning retention levels with a client’s operational realities and financial tolerance, identifying losses that may already be absorbed indirectly through inefficiencies or premium structure, and assessing readiness to manage claims within a retention framework. SIRs can be thoughtfully positioned as a proactive strategy rather than a reactive adjustment.

There are also clear advantages for agents. SIR solutions are not widely utilized across the middle market, creating differentiation in how programs are structured. As clients grow in size and sophistication, SIRs offer a pathway to evolve coverage without displacing existing relationships.

“This evolution supports long-term partnerships, allowing agents to guide clients from more traditional risk transfer agreements into increasingly sophisticated risk financing strategies over time.” Hollis said.

The Importance of Carrier Partnership

Carrier selection becomes especially important in SIR programs.

Not all insurance carriers are equipped to support retained risk structures, particularly in complex product liability environments. Even among those that can, many limit loss-sensitive program offerings to national account clients, where qualifications often depend on workers’ compensation being structured on a loss-sensitive basis. “The most effective partners bring a combination of specialized underwriting expertise in product liability and dedicated claims resources that extend beyond traditional coverage,” Hollis said. “They also provide loss control and risk solutions that help insureds better manage exposures within the retention.”

Some carriers, like The Hanover, have dedicated complex general liability teams that can offer SIR structures on general liability programs for a range of customers. They can also maintain guaranteed cost structures for other lines, allowing clients to take on risk selectively where it aligns with their strategy. These capabilities enable more tailored program design as client needs evolve.

In complex liability segments, specialization matters. Precision in underwriting, claims and risk advisory support can significantly influence outcomes across the entire insurance program.

A Strategic Path Forward

Self-insured retentions are not a universal solution, but in today’s product liability landscape, they are increasingly relevant. Market dynamics will continue to evolve, while underlying loss trends — driven by litigation costs and severity — remain persistent. Organizations that take a deliberate approach to retained risk today are better positioned to navigate the market cycles of tomorrow.

For qualified insureds, SIRs can improve access to coverage, stabilize costs and introduce greater control over claims outcomes. For agents and brokers, this presents an opportunity to grow alongside clients by delivering more value-added strategic advice and placing business more effectively in challenging markets. Partnering with carriers like The Hanover that have the expertise and flexibility to support retained risk structures is critical. Together, these relationships help build insurance programs that are more resilient and better meet customer needs.

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

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

The Hanover Insurance Group, Inc. is the holding company for several property and casualty insurance companies, which together constitute one of the largest insurance businesses in the United States. The company provides exceptional insurance solutions through a select group of independent agents and brokers. Together with its agents, The Hanover offers standard and specialized insurance protection for small and mid-sized businesses, as well as for homes, automobiles, and other personal items. For more information, please visit hanover.com.