I've been remote for 4 years and it all started at a company who didn't have a remote culture, but my boss wasn't too worried about me going remote. I was on a software team for 2 months before finding out I needed to move. I told my boss I had to move in 4 months, but I really wanted to keep my position and wanted to switch to working remotely. More than half of the engineering team at the time was offshore; however…
There were even times in the past where my boss talked to me about wanting me to be physically in the office more. These days I often only go in twice a week for less than half a day for meetings. Recently our boss worked remotely for a month from the other side of the globe. Our head of sales is considering moving 1000 miles away while staying on remotely.
We're tight knit and small enough that it hasn't been difficult to accommodate more remote work.