This session explores how technology improves group captive operations, told through two live programs, one homogeneous (transportation) and one heterogeneous, and approached from the captive manager and the captive owner. We show where data integration, automation, and AI were applied to specific operational challenges, with measured results across onboarding time, underwriting turnaround, data quality, and operating costs. Innovations are presented with the investment required and challenges faced during the process. Together they put group owners and members on a path to better outcomes: how to calibrate renewals on live data, evaluating prospective members with efficiency, catching loss trends across the membership as they emerge, and giving members a clear view of their own performance. Single-parent owners benefit from the crossover: technology can sharpen the decisions unique to them, from stress testing surplus and comparing retention options to adding new lines of risk and structuring reinsurance, all underpinned by a live view of the captive’s financial and operational data. Audience members leave with a clear understanding of how to develop a realistic technology roadmap.

Following this session, attendees will understand how to benchmark their own captive’s operating performance, understand how to isolate which improvements transfer to their own structure, and know how to build a realistic technology roadmap, weighing investment against payoff, with lessons drawn from common pitfalls.