Protection you need. Savings you deserve.

Small and midsize companies are paying more for healthcare every year—with fewer cost controls and narrower coverage in return. 

There is a better way: Roundstone’s captive insurance.

Protection you need. Savings you deserve.

Small and midsize companies are paying more for healthcare every year—with fewer cost controls and narrower coverage in return. 

There is a better way: Roundstone’s captive insurance.

The roundstone Guarantee

You’ll Save Money over 5 years—or we’ll make up the difference

Available exclusively to groups moving from fully insured coverage. 

We pioneered captive insurance for small and mid-size businesses because we believe everyone should have access to quality, affordable healthcare. We combine innovative cost strategies with an employer-first approach to deliver industry-leading savings so you only pay for the healthcare that’s used.

Cost Controller

With the most efficient financial structure on the market, our medical group captive smooths out volatility and returns the most value to you.

Verified Partners

Our network of preferred TPAs and PBMs offer the transparency and value needed to deliver the lowest Per Employee Per Year (PEPY) cost in the industry.

Savings Accelerator

Our data-driven platform recommends the most effective and fully-vetted cost containment solutions available to prevent and tackle bigger claims.

Captive insurance structure showing how reinsurance, the captive pool, and employer claims layer together to spread risk

Stop chasing lower rates. Save annually on premiums and reinvest the rest.

At Roundstone, we build quality, affordable self-funded health insurance plans tailored to the true needs of your business—no hidden costs and no overpaying for coverage your employees don’t need.

You pay for claims directly, up to a pre-defined level. From there, protection kicks in: employers share risk through premiums paid to our captive pool, and stop-loss insurance protects against larger claims. Any unused healthcare dollars are returned to where they belong, your hands.

That’s the foundation of our captive: Low up-front cost, predictable premiums, transparent data, and higher returns with an average savings of 25%.

Captive insurance structure showing how reinsurance, the captive pool, and employer claims layer together to spread risk

Good partners make insurance work for you—not the other way around

Self-funded insurance depends on a strong network of partners. They can make the difference between a plan that functions and one that performs.

Our approach guides you to the right partners, preserving access to the doctors, pharmacies, hospitals, and providers your employees use.

We don’t believe in “one size fits all”. We let the data guide us. The best partners offer complete claims visibility and a streamlined process for implementing cost containment solutions. You have the flexibility to choose your own or select from Roundstone’s Verified Partners.​​

Roundstone summary row showing 7% collateral and 30% fixed costs
Bywater, a Roundstone company, logo

Our transparent TPA is built for self-funded insurance

Aligned with Roundstone’s employer-first solution, our medical Third-Party Administrator (TPA) offers one of the lowest Per Employee Per Year (PEPY) costs on the market without sacrificing service or administrative expertise.

Calculate your savings

See how much you could save with Roundstone versus traditional insurance

Over 5 Years, You Could Save

$3,397,035

Per Employee Per Year (PEPY) Costs

Current Costs
$20,000
with Roundstone
$12,553
A man in a denim shirt smiling during a one-on-one meeting with an advisor
Clarity now over costs later

Your high-risk employees deserve a more thoughtful savings approach

we’re here to answer questions

What Employers and Advisors Want to Know

A medical group captive is a self-funded health insurance model where employers share risk to gain stability, transparency, and buying power.

Employers using fully-insured pay a fixed premium for the carrier to take 100% of the risk and keep all profits. Captives allow employers to band together to control costs and receive refunds for better-than-expected claims.

Employers using level-funded pay a fixed monthly fee to cover administrative, claims, and stop-loss insurance expenses. Any surplus may be partially refunded at the carrier’s direction. With captives, you gain control—full data ownership, plan flexibility, and the ability to keep any savings.

Roundstone works with employers ranging in size from 25 to 1,000+ eligible employees.

Yes, with the right partners, transitioning to self-funding is easy. Roundstone assigns a dedicated Customer Outcomes Manager to guide clients through the process. Your third party administrator (TPA) then handles day-to-day administration and claims.

The change has resulted in lower-cost coverage, higher-quality care, and happier employees. We’re pleased to be part of Roundstone’s network of advisors and also one of Roundstone’s employer groups participating in the captive. It was a smart choice.

Senior VP of Sales, Totem Solutions

Ready To Take Back Control Of Your Healthcare Costs?

We’re helping businesses change self-funded health insurance for the better. Contact our team to get started on a quote today.

Have a question about group captive insurance? Ask me anything.