Strategies for Small Businesses to Achieve Captive Insurance Alignment

In this episode of The Edge of Risk Podcast, host Joel Appelbaum welcomes Courtney Boles, director of operations at Management Services International, to discuss how small businesses can achieve organizational alignment for captive insurance success. Many small businesses operate without dedicated risk or insurance teams, making it difficult to launch and sustain a captive program. Ms. Boles shares why alignment across leadership and staff is critical to overcoming these challenges and ensuring long-term results.

She explains how to identify internal champions, engage multiple departments in decision-making, and address skepticism with clear education and accessible language. The conversation also explores how structured communication, regular check-ins, and effective annual meetings help keep captives aligned as business needs evolve and risks change.

Looking ahead, Courtney highlights the role of innovation—from parametric triggers to advanced analytics and artificial intelligence—in expanding opportunities for small businesses. Once the domain of larger insurers, these tools now allow smaller organizations to better customize coverage, manage emerging risks, and strengthen their captives' performance. Together, her insights offer a practical roadmap for business leaders seeking to balance growth, manage risk, and build a successful captive program.