Beyond the Savings: Evaluating Captives for Long-Term Success

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Date: Thursday, September 3, 2026
Time: 2pm ET | 11am PT
Cost: Complimentary
Produced and Sponsored by: Roundstone

As the market for captive insurance solutions expands, advisors face the growing challenge of comparing a variety of complex solutions for their clients. On the surface, many proposals promise significant cost savings and benefits, but what truly separates a high-performing, sustainable captive from one that looks good on paper?

To equip advisors with the necessary tools for this critical evaluation, we invite you to a comprehensive webcast designed to deepen your due diligence process. This session moves past the initial sales pitch to explore the fundamental pillars that support a successful captive insurance program. We will provide a clear, actionable framework for assessing the less obvious, yet crucial, components that determine long-term value and stability.

Join this insightful session where you will learn to:

  • Understand how different approaches to underwriting can impact risk selection, pricing stability, and the overall financial health of a captive over time.
  • Discover why the quality of the service model affects claims management, reporting, and client satisfaction.
  • Learn to identify effective, proactive cost containment strategies versus purely reactive measures.
  • Gauge if a captive's strategic vision aligns with your clients' future goals.
  • Leave with a structured approach to confidently distinguish between an attractive proposal and a genuinely sustainable long-term insurance partner for your clients.

Speakers:

Jamie Debenham | Regional Practive Leader | Roundstone Insurance
Jamie is a Regional Practice Leader at Roundstone, where he covers the Arizona, Colorado, New Mexico and Utah regions. With years of experience in employee benefits, he provides innovative solutions for advisors, and their clients, that improve the health of the population while also containing costs.

Ian Woidke | Regional Practice Leader | Roundstone Insurance
Ian is a Regional Practice Leader at Roundstone, where he covers the Alabama, Arkansas, Northern Florida, Louisiana and Mississippi regions. Ian helps to translate complex healthcare concepts into clear, actionable strategies that drive long-term value for small to mid-sized employers.

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