My team at Stripe was scattered all over, during COVID our company was fully remote, and prior to that I worked remotely on a presidential campaign. All of those were great experiences and, in their own ways, necessarily/understandably remote.

Compared to the early days at Gusto and my own startup, though, in-person has very real benefits that (in my opinion) are worth the challenges in hiring. I don’t know that it will always be true and can’t rule out that we’re wrong.

Having internal users and domain experts there in person makes a huge difference. It’s not impossible to do remotely, and maybe the tradeoff doesn’t make sense forever, but it’s worked well thus far.