Affordable health benefits for small to mid-size businesses!

A Better Way To Do Employee Health Benefits

20 Years and Growing Strong 

Roundstone was founded in 2003 with the mission of creating a better alternative for small and midsize businesses to manage their health benefits. As pressure mounted to provide better funding models for healthcare coverage, Roundstone responded with innovation, growing from a stop-loss reinsurer into the first medical group captive of its kind. 


The captive was a fresh new approach to self-funding. It allowed smaller businesses (25-1000 employees) to take advantage of the benefits of self-funded insurance that previously only larger enterprises could enjoy: flexibility, control, transparency, and savings. By banding smaller companies together in a shared-risk community, they were protected from volatility and could be rewarded with extra savings, which could then be invested back into the business.


What began as an entrepreneurial vision of creating a better life for his family and for his employees for Roundstone’s founder and president Michael Schroeder, has evolved into a thriving 140-person company with more than 700 employers participating in its Group Medical Captive. Throughout its history, Roundstone’s prioritization of the well-being of people has remained a guiding light.


“Our success is a testament to the dedication of our team and our growing network of advisor partners who share our employer-centric values. We will continue to innovate our solution and advocate for affordable, high-quality healthcare and a better life for all.” – Mike Schroeder, President and Founder, Roundstone

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.

2023 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.

Subscribe to Our Newsletter

Stay in the know with monthly updates right to your inbox.

"*" indicates required fields

What is your role?*
This field is for validation purposes and should be left unchanged.