Roundstone careers

Roundstone is an innovative employee health benefits company. We help small and midsize organizations offer competitive benefits at a lower cost by self-funding their health insurance through our group medical captive.

The Roundstone Captive enables companies to self-insure safely by pooling hundreds of employers together to share risk and save money. With easy onboarding and personalized support every step of the way, the Captive offers control, flexibility, transparency, and returns all savings back to employers where they belong.

Unlike other captives that outsource their underwriting to behemoth insurance companies, Roundstone has underwriters in-house that specialize in pricing stop loss coverage for businesses sharing risk in a group captive.

In an industry shrouded in misaligned incentives, we believe in always aligning with the employers’ best interests and remain committed to our mission – quality, affordable healthcare and a better life for all.