FORTY Under 40: Brett Stefani
Brett Stefani, assistant vice president / shareholder, Innovative Captive Strategies.
Stefani began his career with Innovative Captive Strategies (ICS) in 2014 and now helps lead the strategic direction and growth of various of its captive programmes. This involves working closely with business owners to deliver alternative insurance financing strategies that promote long-term cost stability, profit retention and greater control within the insurance marketplace.
With more than a decade of property/casualty experience, Stefani provides experienced leadership and serves as a key liaison between captive owner clients and the professional partners supporting their programmes. He also plays an integral role in expanding the ICS agency partner network by identifying and developing relationships with high-quality brokers committed to offering alternative insurance solutions.
Stefani began at ICS as an intern while completing his BA in Accounting at the University of Iowa, graduating in 2016. He earned his CPA licence after joining ICS full time in 2017 and holds his chartered property casualty underwriter (CPCU) designation. To further enhance his leadership and sales expertise, he completed the Waukee leadership institute programme in 2020.
An active community member, Stefani and his wife, Megan, volunteer with Big Brothers and Big Sisters of Central Iowa. He is the proud father of two children, Lynnie, two and Scottie, nine months, and enjoys travelling, golfing, playing basketball and reading.
Looking back at your journey over the past year, what accomplishment are you most proud of, and how has becoming a FORTY Under 40 finalist influenced your perspective on that achievement?
In 2025, I helped lead a complex transition for a group captive that approached us because it was being non-renewed by its reinsurance carrier due to a lack of critical mass. After a comprehensive evaluation, we executed a novation that transferred the captive’s assets and liabilities into an existing ICS group captive. This provided a long-term, sustainable solution for member companies who otherwise faced uncertainty heading into renewal. It was a unique and challenging situation, and I’m proud that we delivered an outcome that served every stakeholder’s best interest.
Being named a FORTY Under 40 finalist has made me reflect on that project differently. At the time, I was simply focused on trying to find the best long-term solution for the members of that programme. The recognition wasn’t something I expected, but it reminded me how impactful our work can be for the people and businesses involved.
What key challenge did you face in your work this year, how did you overcome it and what did it teach you about leadership at this stage of your career?
One of the biggest challenges this year has been balancing the growing interest in captives with the reality of captive and carrier risk appetite. More companies than ever are exploring alternative risk solutions, but that enthusiasm doesn’t always align with what a captive is able to solve.
Transparency and timely communication are just as important as expertise in building long-term trust with clients and partners.
I learned that leadership at this stage of my career requires guiding people through complex decisions, setting expectations early, and delivering information as soon as it’s available, even when it isn’t what they hoped to hear. This experience reinforces that transparency and timely communication are just as important as expertise in building long-term trust with clients and partners.
In what ways have you tried to push innovation or rethink traditional approaches within your sector, and what impact has that had on your team or organisation?
One area where we’ve pushed innovation within the captive space is in rethinking traditional liability limit structures. Historically, most ICS group captives operated at lower limits, but through a significant amount of analysis, benchmarking, and evaluation of long-term loss trends, it became clear that increasing policy limits in various ICS captives would better position each programme for the future.
We presented the analysis, laid out the implications, and facilitated discussions – but the decision itself rested entirely with the members. Through this process, our organisation improved how we present complex material, sharpened our recommendation process and promoted more collaborative discussion with captive owners and agency partners.
How do you see your role evolving over the next three to five years and what initiatives are you most excited to pursue as you continue to grow professionally?
I see it evolving into one that has greater influence on the strategic direction of our captive operations. I want to help shape our roadmap – how we grow the business, how we standardize excellence across captive teams, and how we leverage technology to improve the client and broker partner experience. I’m most excited about leading initiatives to leverage captive solutions for even more challenges in the marketplace.
Broker partners and customers are continually more comfortable with leveraging captives as a risk financing strategy. In turn, they’re looking to us to present more ways these strategies can create a more efficient manner of funding for an organization’s risk. We also have an immense amount of young talent in ICS, and I’m passionate about helping develop future leaders in our organization. I look forward to continuing to work with newer captive consultants and sharing real-world perspective to help accelerate their learning.
Many FORTY Under 40 winners are recognised for both business success and broader impact – how do you balance professional excellence with contributions to your community or industry landscape?
I’ve learned it’s easy to convince yourself you’re too busy to give back, but in reality, you usually have more time than you think – and whatever time you do give ends up being deeply fulfilling. My wife and I are both passionate about volunteering, specifically with children. She and I have volunteered together at Big Brothers Big Sisters of Central Iowa for the past seven years. I’ve also had the opportunity to participate in a newer initiative between Big Brothers Big Sisters and our parent company, Holmes Murphy, where students spend time in our office to gain exposure to a professional environment. It can be tough to carve out the time, but I’ve learned it is always worth it, and it leaves me more energised and focused in my work.
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