Tech-Driven Captive Management: How Automation Is Reshaping Feasibility, Talent, and Growth

Captive management is entering a new era of automation, accelerated formation timelines, and data-driven strategy. In a new Captive Insurance Company Reports (CICR) interview, Captive Simple cofounders Whitney Benson and Brandon White share how technology is redefining feasibility studies, operational efficiency, and captive scalability.

The executives discuss why traditional feasibility processes—often involving numerous stakeholders and lengthy timelines—are ripe for transformation. They outline how automation and artificial intelligence can reduce costs, streamline workflows, and enhance the ability of captive owners to interpret data, make strategic decisions, and grow their programs.

The interview also highlights emerging trends in captive utilization, including increased interest in stop-loss, broader use of large language models for risk analysis, and a growing emphasis on optimizing existing captives rather than treating them as static structures. Ms. Benson also provides an update on the rapidly expanding Canadian domiciles in British Columbia and Alberta, where new formations and broker education initiatives are gaining momentum.

From accelerating feasibility studies from months to weeks, to using machine learning models to support underwriting and strategic planning, Captive Simple offers a glimpse into how technology is reshaping captive insurance company formation, management, and long-term value creation.

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Innovative Captive Management Technology: An Interview with North American Vendor Captive Simple

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Innovative Captive Management Technology: An Interview with North American Vendor Captive Simple