Navigate Captive Insurance With Confidence

Explore helpful resources on captive insurance including blogs, case studies, webinars and more.

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Webinars & Events

Webinars and Events

Funding Basics
Roundstone Team

Understanding Stop Loss Insurance

Stop-loss insurance protects self-funded employers from catastrophic claims by pooling risk with similarly sized businesses through a group captive plan.

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S2 EP 3: Transforming Healthcare Navigation Through Strategy & Service

Exploring how Steven Chavez, Vice President of Navigation Service Delivery at Rightway Healthcare, and his team are redefining care navigation through technology and human guidance—and why Roundstone partners with them to deliver real value for employers and employees.

S2 EP 2: Smart Hospitals: Innovation, AI, and the New Blueprint for Healthcare Systems

A conversation with David Sylvan, Chief Strategy & Marketing Officer at University Hospitals, on how University Hospitals is redefining what it means to be a “smart” healthcare system—leveraging AI, partnerships, and innovation to deliver better outcomes, streamline operations, and create value across the care continuum.

S2 EP 1: Leveraging AI for Innovation in Healthcare

Mike Schroeder sits down with Brandon Cornuke, Senior Director of Innovation at University Hospitals, to explore how AI is transforming patient care, hospital operations, and cost management. From fall prevention and virtual nursing to AI-powered patient follow-up and a system-wide “problem engine” that elevates frontline insights, Brandon shares how University Hospitals is building smarter, safer, and more efficient care environments while addressing workforce shortages and rising healthcare costs.

Featured Resources

For Advisors
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Roundstone University

Advisors can learn the value of captive health insurance with resources designed to help you educate clients and confidently position self-funded insurance.

Roundstone ecosystem diagram connecting Advisor, Employer, Roundstone Group Captive and Stop Loss Insurance, third-party administrator with provider network and pharmacy benefits manager, and cost containment solutions

Advisor Toolkit

The Advisor Toolkit provides client-ready resources to help you win proposals and stand out—plus tools to showcase Roundstone’s captive savings with confidence.

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Certification Programs

Get certified in captive and self-funded strategies to differentiate your approach and strengthen client trust.

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Self-Funding 101: What Is a Captive?

A group captive health insurance plan allows small to midsize businesses to band together, pool risk, and save money—while maintaining control.

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Self-Funded Health Insurance: The Complete Guide to Taking Control of Your Healthcare Costs

With self-funded health insurance, your company pays for employee healthcare claims directly, rather than paying premiums to an insurance carrier.

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Understanding Stop-Loss Insurance

As a group captive insurance plan, stop-loss insurance allows you to enjoy self-funding by pooling resources with other like-sized businesses.

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