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Better Benefits. Better Life.

Helping employers do employee health benefits better, together.

Making the Switch to a Self-Funded Health Plan

Some businesses believe that they have no choice when it comes to employee health benefits. Or they think that making a change is complicated and risky. So they stay with their current insurance company, and accept a double digit cost increase each year.

We believe you deserve a better – and smarter – alternative in company healthcare: The Roundstone self-funded health insurance solution, a group medical captive.

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How Self-Funding Captive Insurance Works

Self-funding is more flexible, cost-effective, and provides greater control and visibility into cost-drivers compared to traditional insurance.


For small to mid-size companies, however, self funded insurance has not always been a practical choice for company healthcare. Roundstone makes it possible with the pooling of many employers in our group medical captive, the first of its kind. Since 2005, we have proven that banding employers together to achieve the efficiency and scale of a larger organization is the better way.

Our Guarantee to You

Two-thirds of our customers save enough in their first four years with us to pay the claims for their entire fifth year. And 100% save money, full stop. 

 

You will save money in the first five years or we’ll make up the difference. That’s our guarantee to you.

Watch and see how Roundstone helps employers provide better healthcare at a lower cost.

Roundstone By the Numbers

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average annual savings compared to fully-insured.

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average distribution
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unspent captive premium distributed pro rata in 2022.

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Why Roundstone?

It starts with the way we make decisions. It shapes how we work with advisors and other partners. You feel it in the level of service that we provide. In everything we do, we are always aligned with the best interests of employers. Alignment is in our DNA.

We’ve Got Your Back

Our dedicated team provides personalized service - a one-stop shop of experts, advocating for you.

Full Disclosure

We simplify your claims data and provide regular reporting, giving you transparency from dollar one.

Freedom of Choice

You have control over what your plan covers, ensuring your policies serve all employees and staff members.

Cash Back

Pay only for what you use and keep 100% of unspent claim funding and unspent pooled stop loss premium.

What Our Customers Say

Do Your Self-Funding Research

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2025 Roundstone
Medical Captive Forum

April 30 & May 1, 2025 | Cleveland, Ohio
Join us in celebrating the 10th anniversary of this transformative event as it returns to Cleveland. Explore how Roundstone’s Medical Captive Forum has paved the way for empowering employers with cost-effective healthcare solutions and be part of shaping the future of employee benefits.
Register Now
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The Distribution Explained

How Partnering with Roundstone
Delivers Client Success
Since its inception, Roundstone has delivered $91.8 million in surplus back to captive participants. In this webinar, you’ll discover the unique strategies, best practices, and core philosophies that enable Roundstone to maintain a financially efficient and consistent captive, resulting in annual cash distributions and guaranteed savings to employer clients.
Watch On Demand
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The CFO’s Guide to Managing Escalating Healthcare Costs

Explore the financial impact of current employee benefits trends and discover if self-funding through a group captive is right for your company's healthcare. Download the eBook now.
NEW!
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Is Your Company a Good Candidate for Group Captive Insurance?

Not sure if you could make a self-funded plan work for your organization or client? We've got you covered! Get this handy checklist and see.
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The Roundstone Guarantee: How It Works

By participating in our group medical captive, we guarantee that you will save money in the first five years or we’ll make up the difference. Download this fact sheet and learn how it works.

3 Easy Steps to Get Started:

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STEP 1:
Schedule an Intro

– Learn about Self-Funding –

– Engage your Advisor –

– Request a Proposal –

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STEP 2: 

Make a Choice

– Review Your Options –

– Customize Your Plan –

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STEP 3:
Start Saving

– Enroll –

– Implement –

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