Better Benefits. Better Life.

Helping employers do 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 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: The Roundstone self-funded health insurance solution, a group medical captive.


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 practical. 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 Celebrates 20 Years of Self-Funded Insurance

20 Years and Growing Strong

Roundstone proudly celebrates 20 years of innovation, growth, and a commitment to a better life for all. In 2003, we launched the Group Medical Captive, the first of its kind, and revolutionized the self-insurance industry. Now small to mid-size companies can leverage the same risk predictability as the Fortune 500s.

Watch Our Story

Roundstone By the Numbers

0 %

average annual savings compared to fully-insured.

0 %
average distribution
to captive participants.
$ 0 M

unspent captive premium distributed pro rata in 2022.

0 %

latest retention rate
from captive.

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


Fixing Healthcare and Taking
Back the American Dream

A Fireside Chat with Mike Schroeder and Dave Chase
This can’t-miss fireside chat will feature two industry leaders discussing how employers can save the American dream and change the lives of families and communities by making one simple change to their health benefits plans. Register now to find out what that one change is!
Register Now
2023 Summer Breeze Logo

2023 Summer Breeze Webinar Series

A Trip to Cost Containment Island
Want to explore the latest trends and solutions in cost containment for self-funded health plans? Join us for a trip to Cost Containment Island where you can discover a health plan’s biggest cost drivers and tried and true methods to stabilize and reduce them. Our expert guides will lead you to a treasure of useful information.
Watch On Demand

Essential Guide to Self-Funding for HR Executives

With advice and tips from a team of experts, these comprehensive guidelines will help HR managers and anyone responsible for benefits in an organization to better understand how self-insurance works.

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.
The-Roundstone-Guarantee-Handout-Thumbnail_savedforweb_roundstone insurance

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:


Schedule an Intro

– Learn about Self-Funding –

– Engage your Advisor –

– Request a Proposal –


STEP 2: 

Make a Choice

– Review Your Options –

– Customize Your Plan –


Start Saving

– Enroll –

– Implement –

google-site-verification: googled856892fcb729e47.html