Season Wei is a sophomore at Middlebury College, where she studies International Politics and Economics and competes on the Women’s Golf Team. She grew up in New Jersey and first learned about captive insurance in a political science course at Middlebury, which led her to apply for this summer’s internship.
This summer, Season interned with the Department of Economic Development (DED) at the Vermont Agency of Commerce and Community Development (ACCD), where she supported research projects in international trade and captive insurance. She also worked behind the scenes at the 2026 VCIA Annual Conference, helping with booth operations and recording interviews for the Vermont Captive Insurance Emerging Leaders (VCIEL) Student Conference Scholarship video project.
Our Spotlight series usually features the captive owners and service providers who make up Vermont’s captive insurance community. Workforce development is a big part of keeping that community strong, and initiatives like VCIEL exist to introduce students to careers they may never have considered. So for this edition, we wanted to hear from someone seeing the industry for the first time. We spoke with Season about how she found captive insurance, what surprised her, and why she’d recommend it to other young people.
How did you hear about the captive insurance industry?
Having grown up in New Jersey, I had never heard of captive insurance before coming to college in Vermont! I was first introduced to captive insurance in one of my political science courses at Middlebury College. My professor mentioned that Vermont is the number one domicile in the world, so I decided to do some research to get an idea of what it entailed. The more I read about it, the more interested I became. As a result, I applied to this internship to dive deeper into captive insurance, a small but unexplored industry.
What made you interested in this captive insurance economic development internship with Vermont?
As a student at Middlebury, I have reflected the college’s dedication to a global perspective. Middlebury is very well known for its language programs, but more broadly, there is a strong emphasis on understanding different cultures, markets, and ways of thinking. Thus, when I first learned about captive insurance, I was excited to apply for this internship because while it related to my coursework in political science and economics, it was also something completely new and unfamiliar, and I was eager to try something that I had never done before.
Has anything surprised you so far about the industry?
One thing that has surprised me the most is the global reach and influence that captive insurance has not only in Vermont, but also around the world! In the United States, 39 states and jurisdictions are active captive insurance domiciles. Internationally, there are over 70 jurisdictions worldwide. Although captive insurance is a small industry, it brings together so many people from every corner of the globe.
Would you recommend the Vermont captive insurance industry to other young people as a future career path?
Yes! A career in captive insurance will not only help you develop important research, data analysis, and strategic planning skills, but more importantly, it will introduce you to a wonderful network of professionals who will support you and are very experienced in the industry. One of the benefits of being a small industry is that it encourages you to build deeper connections with the people you work with, which makes the career more fulfilling in the long run. Not only that, but being able to work and live in Vermont is an experience that few get to enjoy but is worth it, as its beautiful environment will allow you to slow down and live more intentionally.
What did you enjoy about the VCIA Annual Conference?
I most enjoyed being able to assist with so many of the “behind-the-scenes” conference operations, such as helping manage booth operations and recording interviews for the Vermont Captive Insurance Emerging Leaders Student Conference Scholarship video project. I was also able to network with industry professionals from all over the world at receptions and dinners and play at a golf tournament at Williston Golf Club. It was my first-ever conference, and it was an amazing experience knowing that my contributions played a part in helping it run smoothly.
What do you do for fun in Vermont?
When I am not golfing at the Ralph Myhre in Middlebury, I enjoy skiing at the Snowbowl and exploring Burlington’s Church Street Marketplace. What I love about spending time in Vermont is being able to unplug and stay in the present moment. Going to college in Vermont has definitely increased my appreciation for the outdoors and encouraged me to find the fun in its vast beauty.
