Jonathan D. Messick
Senior account executive
Unity Captive Solutions
Personal bio
Jonathan Messick began his career in Weatherford at Magill Insurance and Real Estate, where he covered every role from receptionist to account manager. Drawn back to his native Oklahoma City, he joined Frates Irwin Risk Management Solutions, also known as Acrisure Oklahoma City, progressing from customer service to personal lines before specialising in commercial account management.
In February 2024, he moved to the captive insurance sector, a shift he describes as “challenging and deeply rewarding”. Off duty, Jonathan plays tennis and golf, enjoys shooting, and values time with friends and family. He insists that a healthy work–life balance — and firm boundaries around evenings and weekends — is vital to his success.
At every stage, Jonathan has sought out seasoned professionals, asked even the simplest questions and embraced new challenges. As he looks ahead, there is no doubt that his blend of experience, enthusiasm and self-awareness will continue to serve him well
Can you tell us a bit about your journey into the captive insurance industry? What initially drew you to this field?
I have always wanted to work alongside my dad, Jerry Messick, after gaining four years’ experience on the brokerage side of the insurance industry.
I sought to challenge myself further by delving into how structuring a captive could benefit a client’s insurance programme.
What does your day-to-day role look like, and what has been the most rewarding project or achievement in your career so far?
My day-to-day activities involve collaborating with prospective and existing clients to present options tailored to their specific risk profiles, and assisting them in finding solutions to manage their insurance risk. A key aspect of my role is advising on the formation and management of a captive insurance company as a long-term asset.
One of my most rewarding achievements has been completing the Associate in Captive Insurance (ACI) designation through the International Center for Captive Insurance Education (ICCIE).
I began the programme in February 2024, when I launched my captive career, and have already gained a wealth of knowledge and insight from leading experts in the field. I have completed my last course in June 2025 and will receive my diploma soon.
Have you faced any significant challenges in your role, and how did you overcome them?
One of the biggest challenges I have faced is getting up to speed in the captive space — there is a huge amount to learn. Transitioning from a foundation in commercial insurance to alternative risk has been a steep learning curve. However, I am embracing it and, by staying open-minded and acting like a sponge with industry leaders, I am catching on quickly. I believe I have made significant progress over the past eighteen months and will continue to build on that progress every day.
What do you enjoy most about working in the captive insurance sector, and how do you see the industry evolving in the coming years?
One of the things I enjoy most about the industry is that captives can be applied to any sector worldwide. I have had the opportunity to work with a wide variety of risk profiles, ranging from habitational and healthcare to amusement and water parks, and many others. I also enjoy analysing a business’ existing commercial insurance programme and designing a captive solution that delivers greater control, potential long-term financial stability and risk-management advantages to the client.
I see technology playing a significant role in the captive industry’s growth over the coming years. I believe it will profoundly affect how we learn, model risk, predict claims and manage captives overall. I also think that technology will help to design better processes for identifying loss trends, improving underwriting accuracy and streamlining compliance and reporting.
What advice would you give to other young professionals considering a career in captive insurance?
I recommend first building a solid foundation in commercial insurance. Then approach the captive side of the industry with an open mind and a readiness to learn even more. Enrol in the ACI programme through ICCIE and complete the courses. Be a sponge for the countless industry leaders and experts who are generous with their time and happy to mentor those who are eager to learn.
Are there any mentors or colleagues who have played a significant role in your development?
Absolutely. Jerry D. Messick has been instrumental in helping me to understand the intricacies of captive insurance, from captive 101 through governance, regulation and reinsurance. Another important mentor has been Greg Fears, whose actuarial expertise and guidance have been an invaluable resource throughout my development.
How do you continue to grow your knowledge and skills within such a specialised industry?
I am not afraid to ask questions, no matter how elementary they may seem. It is important to ask, because if I do not, I’ll make assumptions, and those might not be correct. I also believe that learning from seasoned professionals — taking notes and observing how they engage with prospects and clients and tackle their daily responsibilities — is essential to progressing in this industry.
Jerry D. Messick, CEO, Unity Captive Solutions, “Jonathan isn’t afraid to dive into anything and learn it. I can’t teach drive, so it’s been great to see him embrace his ICCIE education and present to clients”
