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[Podcast Recap]: Health Captive Fundamentals — The Ask Us Anything Live Q&A Event

By Maddison Bezdicek — Vice President, Strategic Vendor Services May 19th, 2026

In this episode of Captivating Health Insights, host Maddison Bezdicek welcomed back Dave Gillis, Managing Director, Medical Stop Loss; Joe Parrilli, Chief Business Officer, Health Solutions; and Kevin Hallen, Managing Director, Health Solutions, for a live Ask Us Anything session. Following the three-part Health Captive Fundamentals series — which featured each of these leaders — the conversation continues with answers to real-world questions from employers, advisors, and listeners.

Drawing on their collective experience, the group outlined how captives function in practice — from eligibility and customization to reporting, stakeholder involvement, and long-term strategy. Across each question, a consistent theme emerged: captives are designed to offer flexibility, transparency, and a more collaborative approach to managing healthcare costs.

At its core, the discussion reinforced a central idea — captives are not a one-size-fits-all solution, but a customizable framework that allows employers to align risk, strategy, and financial goals over time.

The episode also addressed common misconceptions around complexity, clarified how captives integrate with existing plan structures, and explored how employers, Chief Financial Officers (CFOs), and consultants can play a more active role once inside the model.

Core Themes from the Episode: Ask Us Anything Live Q&A

Flexibility Is Foundational

Captives allow employers to tailor plan design, vendors, and risk strategy to meet their specific needs.

Transparency Changes the Dynamic        

Access to claims data and financial reporting gives employers and CFOs greater visibility into performance and decision-making.

Renewals Become More Predictable        

A clearer understanding of cost drivers makes the renewal process more collaborative and less reactive.

Operations Remain Seamless        

Employees experience little to no disruption, with captive structures operating behind the scenes.

Risk Is Structured, Not Increased       

Stop-loss protection and defined layers limit exposure while supporting long-term financial stability.

The Role of the Consultant Evolves        

Brokers shift from transactional support to ongoing strategic partners focused on managing claims and performance.

Collaboration Drives Added Value        

Captives create a shared environment where employers exchange insights, strategies, and best practices.

Participation Is Designed to Be Flexible        

From entry requirements to long-term involvement, captives offer adaptability based on each employer’s needs.

Want the Full Story? Listen to Episode 18

This recap highlighted key insights from the Ask Us Anything session and how captives operate in practice — from structure and flexibility to real-world application. Listen to Episode 18 of Captivating Health Insights to hear directly from the experts as they answer common questions and share practical guidance for employers evaluating a captive strategy.

Listen and subscribe on your favorite platforms, including YouTubeAppleSpotifyAmazon MusiciHeartRadioPandora, and Pocket Casts, to stay up to date on how employers can take greater control of their health plans while improving outcomes and long-term sustainability.

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