Heidi Rabtoy and Sherry Dupont, The Captive Sisters

Vermont Captive Spotlight Series

Author: Vermont Captive

Vermont Captive is featuring a series throughout the year highlighting companies and people that service the captive insurance industry. This post features two young professional sisters who discuss their careers in the Vermont Captive industry – how they got there, what they do and what they enjoy.

Heidi Rabtoy and Sherry Dupont are sisters who’ve both chosen to work in the Vermont Captive industry. Heidi is an Assistant Chief Examiner with the Vermont Department of Financial Regulation (DFR) and Sherry is a Senior Account Executive at Aon. Considering both sisters selected the captive insurance field for their careers and that they both grew up in Fairfax, Vermont, we figured they’d have some great insights about the Vermont Captive industry and what it has to offer. Here’s what we learned.

How did you become involved in the captive industry?

Heidi Rabtoy
Heidi Rabtoy

Heidi: I started right out of college at Aon. I was trying to find a job in accounting but was also looking for something a bit different. Something other than working with an accounting firm or in-house with a company. I gained some insurance experience while getting my degree so Aon intrigued me and seemed like a good fit.

Sherry Dupont

Sherry: Honestly, I’d have to say it was my sister mostly. I had majored in business administration, with a concentration in finance at the University of Vermont. My sister really liked the work she was doing and so I thought I’d explore opportunities in the field. Heidi introduced me to Aon in 2008. I left in 2011 to pursue other opportunities within the industry which afforded me some really great experiences and relationships. After 8 years away, I re-joined Aon in 2019.

What is your role with your employer?

Heidi: I am currently an Assistant Chief Examiner. I started with DFR as an Examiner-in-charge. In my current role, I oversee a great team, where we are responsible for overseeing all licensed captives through the review of captive filings and examinations, which typically occur every 5 years.

Sherry: I am a Senior Account Executive at Aon and I manage the day to day operations of a portfolio of captive insurance companies. From accounting to financial reporting, governance and regulatory compliance, we work with our clients to ensure their captive addresses their current enterprise risk and provide consultative services to address any additional opportunities that the captive might be able to assist with. Our clients operate in various industries, including manufacturing, healthcare, construction, transportation, retail and aviation which is great as I love the diversity that these industries bring to my workday.

Why should companies choose Vermont as a domicile for their captives?

Heidi: As a regulator at DFR, I feel we are very approachable, easy to deal with – we really do answer our phones – and really listen to their needs and work hard to address them. Rather than simply acting as regulators, we take a partnership approach because we want our captives to succeed. Also, the service provider infrastructure in Vermont is excellent. We have some of the best captive managers, investment advisors, claims handlers, professional advisers and more, all in one place.

Sherry: I totally agree with Heidi. It’s such an open-door philosophy here. The regulators are open to new ideas and are willing to try to make them work within the framework of the regulations. We encourage our clients to meet with DFR in advance of submitting a business plan to make sure there are no issues that may be problematic, and they are happy to do so.

I would also add that the Vermont legislature gives bi-partisan support to the Vermont Captive industry, with legislation enacted frequently to improve the regulatory process. The Vermont regulators have a deep and broad level of experience which provides flexibility in addressing the specific and unique needs of any organization.

What do you enjoy most about your job?

Heidi: I very much enjoy working with a diversity of companies. There is a saying, playing off another saying, “If you’ve seen one captive, you’ve seen one captive.” That is so true. I love learning new things – about the different industries, businesses and risks being managed – and I learn something new just about every day.

Sherry: I echo what Heidi says here too. The variability of your days is so interesting and engaging. There are new emerging risks that we get to address on a regular basis, from cyber liability to environmental, social & governance initiatives. We get to help provide solutions to manage these various risks. I find that satisfying. Beyond that, I enjoy the people I work with; my clients, the service providers, as well as my colleagues and the management team here at Aon; the industry is tight knit and full of sophisticated people to network with and learn from.

What challenges do you see for the captive insurance industry in the future?

Sherry: Like so many industries, we are experiencing workforce shortages. While some of that is due to attrition, most of it is because the industry is booming. So, I guess it’s a good time for people interested in the industry to apply.

Heidi: At the state level, we haven’t had as much of an issue with workforce shortages. There has been some turnover, but people here tend to stay for long periods of time. We have noticed though that when we do need to replace someone, the pool of qualified talent has decreased some. Knowing that captive managers have been struggling with filling positions, we have been reaching out more to work with them on how to meet filing requirements.

Why do you like living in Vermont?

Heidi: I love Vermont for being such a great place to raise kids – plenty of room for them to grow.

Sherry: People here seem so genuine and good hearted. I have traveled a lot and worked outside Vermont and I don’t think I’ve been anyplace that has that feel, to the extent it exists here.

And when asked the question of whether they would recommend working in the captive insurance industry to their friends, family and colleagues, they replied, almost in unison, absolutely. That really kind of says it all.

To learn more about working in the Vermont captive industry check out our careers page.

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