Health Insurance for 4 employees - 2 in New York, 1 in Maine, 1 in Tennessee. Best options? (I will not promote)
We're a small Delaware LLC I founded and ran by myself for a few years. Headquarters in NY. Now we're converting into a Delaware C Corp, and we're going to have four employees, myself included as 1 of the 4. Think it would be nice to offer the other 3 employees + myself health insurance through the Company.
Not sure how the multi-state employees complicate things or what my best options are? multi-state group plans, individual coverage HRA, PEO (professional employer organization?
Would love something without a huge administrative burden to setup. Would love something where we're paying closer to 500 - 700 per month per employee, instead of 1000+.
Have any recent founders go through this recently? Please help me avoid a ton of silly, painful, expensive mistakes over the next few weeks as I figure out health insurance for my employees. Thanks!
Posted Feb 26, 2026, 3:31 AM UTC