In this video, Courtney Boles of Management Services International explains the two natural stages of understanding that organizations move through when forming and operating a captive insurance company. The first stage focuses on high-level strategy conversations—learning what a captive is, which risks it may address, and how it could align with business goals. These early discussions often evolve as business owners consult brokers, accountants, and financial advisers to determine whether a captive structure is the right fit. Once the decision is made and the captive insurance company is launched, learning shifts to practical execution. This operational phase includes understanding claims processes, policy issuance, roles and responsibilities, regulatory timelines, and filing requirements. As described in the video, the captive manager works collaboratively with the organization to define workflows, establish calendars, and help internal teams understand how to run the program day-to-day.