We've been dealing with a bunch of bullshit related to this lately. The pandemic literally bumped us from 3 employees to like nine (not including contractors) and we used this thing called ClockTree that was mostly "zoom for psychologists" but it also had a marvelous HR module built in for free. Unfortunately Clocktree shut down yesterday so every payroll form, tax form, health department form etc needs a new home. After much digging the smart money seems to be "use Asana" but I hated Asana in beta, used Asana while hating it for like two years, and bought the whole company Ora because it's basically Asana you can use (that bills you from Bulgaria which always puckers my bank's asshole). If you can find a broker you like they can hook you up with insurance. They're likely not going to be able to do much with... two. Costco has pretty good prices for employer health plans but not a lot of versatility but at your stage in the game I don't think you'll beat them.