FORTY under 40: Jennifer Allen
Jennifer Allen, director, insurance & risk solutions, Ilitch family office.
Following completion of an undergraduate degree in finance at Central Michigan University, Jennifer Allen spent five years working in valuation consulting, analysing plant, property, equipment and cash flows for various valuation purposes. She moved to Ally Financial in 2013, where she spent the next 8.5 years. She spent the first half of her time in various risk management and corporate finance roles, then in 2017 joined Ally’s insurance company, Motors Insurance, where she immediately became involved in captive insurance and reinsurance. That role led her to her current role at the Ilitch Family Office, where she has been since November 2021. She is the director of insurance and risk solutions and responsible for the operations, strategy and growth of two captive insurance companies
I stumbled into captive insurance – and it has been one of the most rewarding discoveries of my career
How did you first become involved in captive insurance?
At Ally’s insurance company in 2017. Ally reinsures auto dealer risks, primarily vehicle service contracts, to captives. My role was very expansive and I had the opportunity to work directly with dealers, helping them understand their captive and how to optimise the structure. I also managed an operations team in the group, which allowed me to understand both the customer side of captives and the back-office, operational side. I loved both.
What are the greatest challenges of working in this industry, and what do you find most rewarding?
One is grappling with elements beyond our control – market volatility, regulatory complexity and the intricate nature of certain lines of insurance. These unpredictable factors can make navigating this field particularly demanding. In addition, there’s an ongoing uphill battle with knowledge gaps. Despite captives becoming an increasingly significant part of the insurance landscape, the broader industry still has strides to make in terms of resources, expertise and general understanding of captive structures and their potential.
What keeps me motivated, however, is the reward of overcoming these challenges. Solving complex problems, crafting innovative solutions and developing risk financing strategies that make optimal use of captives are what I find most fulfilling. Each hurdle presents an opportunity to push boundaries and create strategies that deliver value that’s what makes this industry so fascinating to work in.
Would you recommend the captive insurance industry to young people as a future career path?
When I graduated, a career in insurance wasn’t even on my radar, and I certainly had no idea what captive insurance was. Like many in the industry, I stumbled into it – and it has been one of the most rewarding discoveries of my career. Right now, the broader insurance industry faces a looming talent gap, and the need for young talent has never been more critical. Captive insurance, in particular, offers a unique and compelling career path. Beyond addressing this talent need, I’d encourage young professionals to consider captives because the industry is truly fascinating. Captive insurance provides endless opportunities for growth and learning. It’s a dynamic space that is constantly evolving, allowing professionals to blend creativity with technical expertise. It’s never boring – in fact, the pace of change and innovation keeps things exciting. Whether you’re drawn to analytics, problem-solving, or innovation, there’s something here for everyone.
What developments do you see ahead for captives?
There are several developments I’m eager to see evolve. AI and technological integration are at the forefront. As technology continues to advance, the ability to generate real-time underwriting data and leverage predictive models for underwriting could lead to a significant transformation within the industry. Captive insurers, especially newer and more agile ones, may be uniquely positioned to integrate AI into their operations, utilising data in ways that go beyond traditional applications. Another exciting area is the response to emerging risks, with solutions such as parametric insurance driving innovation.
Climate risk, in particular, acts as a catalyst for growth in this space, and I anticipate parametric solutions will continue to expand as a viable option in the market. Regulatory evolution and the rise of new captive domiciles are also shaping the global captive landscape. Each year brings new jurisdictions into play, and I’m curious to see the opportunities these emerging domiciles will create for the industry as a whole.
Lastly, as captives now represent a significant share of the broader insurance market, the potential for collaboration between captives and traditional insurers is more promising than ever. Whether through fronting arrangements or other partnerships, I’m eager to see how these relationships develop and contribute to the evolution of the industry.
Do you think your long-term future remains in the captives market?
Yes, I absolutely see my long-term future in the captives market. The industry offers a unique combination of challenges and opportunities that continually push me to grow professionally. The dynamic nature of captives – addressing emerging risks, adapting to regulatory changes, and finding innovative solutions – keeps the work exciting and intellectually stimulating. What excites me most about this space is its continuous evolution. Whether it's integrating AI and advanced technologies to enhance underwriting practices or addressing cutting-edge risks like climate change through solutions such as parametric insurance, captives are at the forefront of innovation in the broader insurance world. Being part of this progressive and forward-thinking field is incredibly rewarding. The captives market combines creativity, technical expertise, and constant learning – all of which resonate deeply with my professional goals and passions. For these reasons, I’m confident that my long-term future lies in this ever-evolving industry.
Click here to read Captive International’s third FORTY Under 40 2025 publication.
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