[BrentOzar]

> Compensate your employees well, have them be independent contractors.

Absolutely, that’s a valid choice. We chose the employee approach because that’s what I would have wanted as an employee: I didn’t want to hassle with health insurance, taxes, vacation, hardware, etc. I wanted to just show up to work and have my employer take care of the rest, so that’s the company I built. (We definitely went overboard trying to make things easier for the employees.)

Most of our competitors in this same space take the contractor approach, and I’d say that’s better for the company for sure. I understand why folks do it, and I don’t think there’s a wrong answer - both have pros and cons. My comment just wanted to lay out a couple of answers to the post’s question, “Why aren’t more companies remote-first?” Hopefully I achieved that.

[PopeDotNinja]

Within the USA, I like hiring people via the employee route. I'm paranoid that one or more contractors will do something like not pay their payroll, file for unemployment, or simply claim they should have been an employee all along. I'll consider contract arrangements for people that are clearly contractors with their own business, people outside the USA, and short term engagements where someone specifically asks in writing to be a contractor. Anyone who doesn't otherwise say so is going to be an employee. I consider the certain overhead of having employees to be insurance against the uncertain overhead of are-my-people-employees-or-contractors shenanigans.