John Fannon, who goes by Jack, is an Account Administrator at Advantage Insurance in Burlington, Vermont, a captive management firm specializing in custom insurance solutions. Jack is responsible for client-facing work, account management, and compliance which expands upon his degree in Economics with a minor in math from the University of Vermont. As a recent college graduate in the competitive realm of Vermont captives, we wanted to get to know Jack, learn about his corner of the captive world, and get his thoughts on working in the captive insurance industry so far.
On getting started in captive insurance
Jack first encountered Vermont’s captive sector “by chance,” while browsing the Department of Financial Regulation website for internship opportunities. After connecting with Brittany Nevins, Vermont’s Captive Insurance Economic Development Director, he learned more about captives and found them to be “an intriguing area of finance with strong Vermont connections.” Using the Vermont Captive Insurance Emerging Leaders (VCIEL) internship list, he reached out to several captive management firms in the state, and Advantage Insurance picked up the phone. He began as an intern in August of 2024 and transitioned to a full-time account management role that October.
On his role and day-to-day at Advantage Insurance
Jack’s day-to-day is driven by interpersonal interactions: managing client relationships, supporting business development, coordinating insurance tasks, and building bridges between accountants and clients. He is involved in the “softer stuff,” as he puts it, while also pitching in on client data needs thanks to some computer science experience. “No two days are alike,” he says, “and working in captive insurance often means finding a solution to a client’s pressing needs.”
On what sets Advantage Insurance apart
Many captive management firms are affiliated with brokerage houses; Advantage Insurance is not. Savvy captive owners appreciate this independence. With over $3 billion in annual premium under management, Advantage affords Jack the opportunity to work with a variety of captive owners—from Fortune 200 companies to small nonprofits. Jack’s teammates also come from a variety of backgrounds, with experience in economics, finance, accounting, banking and underwriting. Such variety allows Advantage to tailor its services to meet each client’s specific needs and allows Advantage employees to apply their specific expertise. Jack states that Advantage “does not pigeonhole clients into [its] systems but instead meets them where they are.”
On his favorite part of the job
“Definitely the clients,” Jack says. “They all have such a wide range of programs, challenges, and personalities. It’s fun to get to know them and help them grow.” Working in captive account management, as with a traditional insurance firm, requires strong client service skills. Jack enjoys strategically facilitating the growth of a client’s captive from the early stages to a place where the captive “flows back” into the parent’s business. He calls it “very satisfying.”
On the most surprising things about the industry
Before beginning his career in the captive insurance industry, Jack did not realize the prevalence of and opportunity for risk management. He states, “Risk and insurance needs are everywhere; everything has an insurance aspect.” Seeing risk everywhere, he says jokingly, is “a blessing and a curse,” but he recognizes the power of proper risk management and the importance of captive insurance as a tool to insulate against those risks. A surprise has been the reach of captive insurance in all types of industries and how many businesses are using it.
On challenges ahead for the captive field
Given Vermont’s dominance in the captive industry, Jack considers the state and the industry at large as inextricably tied. As such, both the state and the industry are facing similar demographic challenges. “It is difficult to retain talent, and we lack young accountants. Even with competitive careers and salaries, a big four accounting firm will usually win out. Captive insurance doesn’t have the same recognition or perceived career growth.” Jack stated that many of his college classmates jumped on the opportunity to move to cities like Boston and New York City without giving careers in Vermont much of a consideration.
Jack also sees an issue with the lack of circulated knowledge about the captive industry. Many people, and not just younger ones, don’t know what captive insurance is. Coupled with a “higher velocity of money, ideas, and jobs in New York City,” as Jack says, “and Champlain College cutting its accounting program, it is not surprising that new grads are looking past captives for their careers.”
On how Vermont stays competitive
Jack made the “conscious but challenging decision” to stay in Vermont, even if larger firms and cities can offer more competitive salaries and opportunities. Vermont offers something different: the ability to work with companies worldwide from Burlington while still being surrounded by natural beauty and living in the countryside.
“Captives are a unique piece of our economy that doesn’t rely on tourism,” Jack says. “It’s a great bulwark.” Even in volatile markets, Vermont’s captive sector remains steady, supported by strong regulation, flexibility, broad expertise and structures, and ties to the outdoor economy—strengths that set Vermont apart as a domicile.
On whether he’d recommend captives to young professionals
“I would be remiss if I didn’t recommend it,” Jack says with a smile. For him, Vermont’s captive insurance industry allows for a blend of lifestyle and career—“ski on Sunday and work with Fortune 500 companies on Monday.” He values the on-the-job learning, the thoughtful onboarding that helps build core accounting skills, and the wide variety of partners and industries he encounters: “In captives, you’re not siloing yourself; you see different businesses and industries.”
On living and working in Vermont
As a lifelong Vermonter, Jack knows the best activities for an outdoorsy young professional and he takes full advantage of them. He enjoys skiing, biking, paddling, and all the other activities Vermont has to offer alongside a growing career. He also values the state’s “density of community,” where it’s easy to connect professionally and socially. He also feels Vermont is “going places,” pointing to ongoing investment from the state in its business development programs. The state and the Vermont Captive Insurance Association invest time in their promotional materials and supporting young and new professionals, and in Jack’s case, they caught the interest of the right person.
