Finding the next generation of captive talent

Captive Review speaks to three promising 20-somethings at different stages of their careers who’ve been through internships and decided to pursue working in the captive insurance industry. We hear how they got involved in the captive sector, their experiences as young people starting in this industry for the first time, and their thoughts on how the captive market can attract and retain talented young people in the future to avoid a much-feared brain drain from the industry

 

A notable highlight from March’s CICA conference was the annual essay contest, where three pairs of finalists presented to an assembled audience of captive professionals their captive solutions for one of three case studies.

All produced extremely accomplished and well-thought-out solutions that proved to the many experienced heads out there that there is talent waiting in the wings for when they eventually decide to retire.

The challenge is finding it and convincing those talented individuals to become a part of and remain in the captive insurance industry.

CICA’s essay contest is one proven way of doing this, and its NextGen scheme has also been a positive initiative for bringing on the next generation into leadership positions, thereby keeping that talent in the industry.

At a time of increased captive formations and utilisation of captives, in conjunction with an ageing workforce, it is arguably more important than ever that firms are searching for and retaining this new talent now.

“We’re experiencing significant shifts in knowledge and skills as senior leaders leave the industry and take their knowledge with them,” CICA president Dan Towle told Captive Review. “We’re also seeing increased demand for new skills and new strategies to deal with today’s host of emerging risks.”

He explained that now is a time for companies to pay attention to their talent pipeline to make sure they are bringing in and developing the talent needed to support any captive insurance programmes.

The State of Vermont and its Department of Financial Regulation, along with the Vermont Captive Insurance Association (VCIA), have also been leaders in trying to recruit new talent into the captive space.

Together with Brittany Nevins, captive insurance economic development director at the Vermont Department of Economic Development, Vermont staff and service providers in the region have been promoting the captive industry in local colleges and online in various ways, such as creating a webpage with more information about the captive industry as a career path.

Because, even in Vermont, where over 600 active captives are domiciled and where there is such an established captive infrastructure, most students are unaware of captive insurance as a career path. As much as anything, it’s about raising awareness of captive insurance as an industry.

To assess the challenge the industry faces with funnelling new talent into the captive space – and keeping it there – Captive Review spoke to three promising new entrants to the sector to find out what initially got them involved in captive insurance and what would entice more people to enter the industry.

Claire Richardson

Claire Richardson joined the captive industry in September 2020 as an intern at Hylant. By June 2021, she was a full-time captive consultant after graduating from Butler University with a degree in risk management and insurance.

She remains at Hylant today, based out of Indianapolis, working with clients and prospects to educate them about captives, conduct feasibility analyses and strategic review reports, and working with regulators and (re)insurers to implement captive insurance structures.

“While a sophomore at Butler University pursuing a marketing degree, I attended a Gamma Iota Sigma (GIS) meeting with a friend, entirely for the free pizza,” she says of how she first heard about captive insurance. “The speaker was so unbelievably passionate and authentic that his message made me come back to more meetings. I kept going throughout the semester and by winter break I was convinced insurance was the place for me.”

Richardson changed her major, and started getting involved with GIS, as well as learning about Butler’s student-run captive.

“I was so enthralled by the captive concept, I was able to work with my professors to sponsor my independent study, allowing me to gain credit for learning the ins and outs of captive insurance,” she adds. “While looking for internships for my senior year, I searched for captive-specific roles. Thankfully Hylant and Anne Marie Towle crossed my path. I took a captive consulting internship at Hylant in the fall of 2020 and never looked back.”

Michael Reavill

Michael Reavill similarly chanced upon captive insurance. Reavill is now 28 and has spent a little over six years with Performa in Vermont.

After starting as an intern, he is now an associate portfolio manager, whose primary responsibility is managing cash and short duration investment strategies for captives.

But it was a chance conversation with a stranger while in his junior year of college at the University of Vermont that gave him his first introduction to captive insurance.

“We struck up a conversation and he told me about a potential internship at a local asset management company, Performa, where he was interning at the time,” he says. “I later interned at Performa, for most of my senior year, working on a multitude of projects.”

Most of his work was focused on the investment side of the business, doing research, financial data analysis and developing more efficient workflows.

“Towards the end of my senior year, my mentor at Performa expressed that the fi rm was pleased and grateful for all the work I did, but that he was not sure they would be able to offer me a job after college,” he adds. “So, at the end of the school year I had done several rounds of interviews at various companies and was fortunate enough to get hired as a staff accountant at what is currently known as OnLogic (formerly known as Logic Supply).”

Less than three months into his job with OnLogic, though, he received a phone call from his old mentor at Performa offering him a job.

The next week he went and interviewed for the position of operations data analyst, and that began his career in the captive industry.

Ryan Guerino

Another well-trodden path into the captive industry is through family connections.

When young people see first-hand through a parent the opportunities that a career in captive insurance can offer, many decide to follow in their footsteps and enter the industry.

That was the case for Ryan Guerino, who was exposed to the captive industry through his father, David Guerino, managing director of KeyState Captive Management.

“In truth, he’s had a major influence on my career path, as I have been able to see what the captive industry has been able to do for him and our family,” Ryan says. “About one year ago now, I sat down with my dad and had a serious talk about my future and the path I had set out for myself. During this talk, he enlightened me on an internship opportunity within his company. I expressed that I was interested and would investigate the internship and the captive industry further.”

He proceeded with the application and interview process and became KeyState’s first captive intern, a position he has held for coming up to a year now.

In that time, he has supported in a range of tasks, including preparing and reviewing drafted audited financial statements, pool participation agreements, reinsurance agreements, captive management agreements, addendums to agreements, and S&P reports.

He has also been responsible for rolling forward financial statements and helped implement a new database through QuickBooks.

His year also included attending the 2022 VCIA Conference, during which time he says he learnt a lot more about what captive insurance is, how it is beneficial to all parties involved, and the growing scope behind the industry.

“Not only did I learn a lot, but I was able to practice and improve my professional communication skills through the interactions and conversations I had with experienced individuals,” Guerino says. “A lot of this took place during my walk through of the many exhibits, and with different receptions and gatherings outside of the complex.”

Positive experiences

Guerino is due to exit the industry this coming summer to pursue his Master of Accountancy, followed by a CPA certification. However, due to his positive experiences in the last year, he says he retains a great interest in returning in the future.

“The captive industry has given me many reasons to stay, including the collaborative culture, career growth opportunities, job security, work-life balance and professional development,” Guerino says.

Like Guerino, Richardson also attended a captive insurance conference early into her internship, where she was able to meet captive professionals in all positions of the industry.

“All of them welcomed me with open arms and offered their support as I began my career,” she says. “I had no idea an entire industry could be this tight knit!”

From then on, Richardson says that one of the main reasons she has stayed in the industry is the difference in work day to day.

“One day I might be working with a grocer’s association and the next I’m working with a hospital system, each with their own unique exposures, risk tolerance, coverage requirements and country-specific regulatory requirements,” she adds. “I love having the ability to work with a variety of industries. I’ve learned so much in the time I’ve been in the captive industry thus far and can’t wait to continue accumulating even more experience.”

Long-term opportunities

Despite having only been working fulltime in the captive space for a short time, Richardson is already confident she will remain in the industry for the long term.

“With the myriad opportunities in the captive industry, I don’t see a need to leave,” she says. “Between the quality of people and clients in the industry and the wide variety of positions, there is way too much opportunity to consider leaving the captive space.”

Having gone through the internship process and established himself in the captive sector for over six years, Reavill also doesn’t see himself leaving the industry.

Like Guerino and Richardson, Reavill appreciates working with others in the captive community and has found everyone to be welcoming and supportive since he began working in the sector.

But he explains that another main reason he has decided to remain in the captive space up until now has been the opportunity for career growth.

“I know I am learning something valuable and specialised in an industry that has a lot more room for growth,” he says. “I do see myself staying in the industry for the rest of my career. The industry provides ample room for professional development and advancement. I have found that working in an industry that is always changing and evolving to be both engaging and rewarding.”

Reavill thinks there are a lot of great online resources available to learn about captive insurance if you know where to look. Equally, he says there are many job opportunities in the industry.

“All of this suggests that captive insurance is accessible and easy to get involved with, but I believe it all comes back to the awareness aspect,” he says. “If people are unaware of the resources and opportunities in the industry, then it might feel less accessible than it actually is.”

Lack of exposure

Part of the problem, Reavill thinks, is that a career in insurance doesn’t often cross young people’s minds as a possibility. Despite attending the University of Vermont, he says he had never heard of captive insurance or even considered a career in insurance.

“I do not recall there being any classes offered on insurance,” he says. “From my perspective, a lack of exposure and education during their college experience makes it far less likely for students to look for and/ or apply for a job in the industry. Creating a general college class offering on insurance at local colleges might stir up awareness and potentially create more interest.”

And despite all the work done in recent years to go into colleges and raise awareness of captive insurance as a profession, even today Guerino finds that peers in his classes have never heard of captive insurance.

Of those who are familiar, he says they’ve usually been exposed to or learned about the insurance industry in general, making it easier for them to wrap their head around the idea of captive insurance.

Guerino thinks it would be very beneficial for captive insurance companies and associations to try and make an impression on college campuses.

“This could be done through career fairs, tabling and setting up activities to attract a crowd, or host seminars in exchange for some sort of incentive,” he says. “I believe all these options would help with exposure and put the idea of the captive industry in the heads of the next generation.”

Industry efforts

The industry does appreciate the challenge it is facing with getting more young people interested in captive insurance as a career.

Richardson recognises that great efforts have been put into getting young professionals into speaking positions at conferences where students are present and thinks the industry should continue to increase the visibility and amplification of young voices.

There have also been efforts to take speaking positions into various club meetings at colleges and universities.

“By investing time and funding into college programmes, especially non-insurance programmes, students will begin to notice and search for internships with the organisations familiar to them,” she says. “This is a fantastic opportunity for both students and employers to have mutually beneficial internship programmes that help grow our ageing industry.”

Nevertheless, Richardson still sees barriers to entry in the industry.

“I was blessed with phenomenal mentors, but the next generation needs mentors as well,” she says. “These barriers can be minimised with the support and guidance of professionals already in the industry.”

Efforts are ongoing to ensure there is more emerging talent taking an interest in captive insurance as a career.

Vermont’s Nevins says the state is working hard to raise awareness about the industry as a career choice and that it’s only the beginning of “really intentional work ahead”.

She explains that new and developing captive insurance professionals in Vermont are coming together with the State of Vermont and the VCIA to create ideas for not only drawing in new captive professionals but also supporting them in their journey, so they stay.

“Captive insurance isn’t something students are exposed to when they are formalising their career goals,” she says. “We really need to develop the language to break down the benefits of this industry and go to students directly.”

5-6 November 2025

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