From Strategy to Execution: The Two Phases of Captive Insurance Education

In our latest video, Courtney Boles of Management Services International (MSI), outlines the two natural stages organizations move through when forming and operating a captive insurance company. The first phase centers on high-level strategic conversations—understanding what a captive is, which risks it may address, and how it aligns with broader business objectives. These early discussions often expand as business owners engage brokers, accountants, and financial advisers to evaluate whether a captive structure is the right fit.

Once the captive insurance company is formed, the learning shifts to day-to-day execution. This operational phase includes understanding claims administration, policy issuance, regulatory timelines, and filing requirements. As discussed in the video, the captive manager plays a key role in defining workflows, establishing compliance calendars, and guiding internal teams through the practical realities of running the program.

📺 Watch the full video on Captive.com to learn how organizations transition from captive strategy to successful operational execution.