This was definitely a big thing I noticed when looking around. A lot of places thought I might be suitable from a technical perspective, but that I lacked remote working experience. I've worked in places where it's common to have colleagues working in different countries for extended periods but never in a fully remote environment.
I do wonder how people get their foot in the door with a good remote company. Did you just get lucky when you were first hired? Did your communication skills have to shine a lot for them to hire you?
My first remote job was for a company I had been working onsite for a few months that also had a small amount of people working remotely. I didn't join the company with the intention of going remote, but at some point I decided I wanted to work remotely so I just asked.
After that I joined Toptal and got a couple of projects through them.
IMO Toptal is not a bad choice to get started in remote work, although long term it's better if you find your own work.
I do wonder how people get their foot in the door with a good remote company. Did you just get lucky when you were first hired? Did your communication skills have to shine a lot for them to hire you?