Affordable Health Benefits for Small to Mid-Size Businesses

Who is Roundstone?

Founded in 2003, Roundstone came together because of a shared belief in quality, affordable healthcare for all.


Named for the town in Ireland where founder Michael Schroeder first dreamed of a company he could start in his hometown of Cleveland, Ohio, Roundstone is on a mission to help small to midsize employers provide affordable, high-quality healthcare benefits that attract and retain the best employees.


The “Original Medical Captive”, our self-funded medical group captive, bands employers together to fund their benefits the way much larger Fortune 500 companies do (with some additional advantages).


This captive funding strategy is an innovative and proven model that effectively shares risk and offers choice, transparency, flexibility, and significant cost savings over traditional fully-insured programs. The average client saves 20% compared to fully insured carriers.


Roundstone is proud to have been recognized as an INC 5000 Fastest-Growing Companies honoree for the past five years.

Inc. 5000 Color Medallion Logo

How Did We Get Here?

2003 Circle

Roundstone is formed and begins offering reinsurance support for a medical malpractice program.

2005 Circle

Roundstone creates the very first self-funded group medical captive insurance solution.

2008 Circle

Roundstone adds a domestic agency company and begins offering specialty program management services.

2022 Circle

Roundstone’s team has grown to 130+ employees, all working together to provide innovative insurance solutions for customers.

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

We're Definitely Not Your Traditional Insurance Company

Health insurance can be frustrating, inefficient, confusing, and unmanageable from an expense standpoint. We’re the opposite of all that. Through our unique approach and the group captive funding model, we are transforming insurance.


Employers can leverage data-informed insights and cost-containment strategies to reduce variable spending and receive a distribution of unused premiums each year. With Roundstone, employers only pay for what they use and keep any money left in their claims account and any unspent dollars in the captive pool.

What Sets Us Apart

All medical captives are not the same. We’ve always done things a little differently to be an advocate for employers. We take pride in helping organizations to attract and retain top talent while saving money.


Freedom of Choice

Flexible plan design and benefits for your needs


Full Disclosure

Data-driven insights to optimize plan utilization and contain costs


Cash Back

Distributions of unspent pool premium, RX rebates,
and retained savings in claims account


Personalized Service

One team dedicated to better outcomes and value for you

Our Services

Being self funded does not mean you go it alone. We partner with your benefits advisor to make it easy every step of the way, from onboarding through implementation and beyond. Your employees will only notice one thing: their better benefits.

Captive Facilities
and Management


Cost Containment

Loss Control





Get Benefits to Shout About

Through flexible plan design, thoroughly-vetted cost containment programs, anonymized analytics, and best-in-class customer service, we’ve gone down every avenue to take the complexity and costs out of healthcare to give you savings and benefits you can recommend to everyone.


In fact, we guarantee that you will save money in the first five years, or we’ll make up the difference.

Learn More About Our Group Medical Captive

Case Studies

See how businesses are benefitting
from self-funded health insurance.

Press Releases

Stay up-to-date with the latest
news from Roundstone.

Medical Captive FAQs

Find out everything you want to know about our Group Medical Captive.

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