I worked at a company for just over two years based in the office and then moved to live in Europe for six months, just returning recently to Canada.
The total company size was around 20 staff & execs at the time. My CEO was ok with it, as I had demonstrated over the past couple years that I was able to work independently and responsibly.
The company itself did not need to make several changes as we already had remote employees, so most of the meetings already had somebody dialling in. We use Slack as well which contains a lot of information. I joined a lot more channels when leaving to try best to keep up with all of the information.
My biggest struggle was feeling disconnected from the company and from my coworkers. I missed out on a lot of information that was informally discussed in the office and felt a lot of anxiety related to my performance, even though I was still producing work at a consistent rate. This started to solve itself partially after getting over some of the general growing pains being in the new environment, and I started having regular fifteen minute Skype chats with a handful of different members of the company so we could better keep in contact.
Another struggle was working from home. I found it easy to get distracted and found myself adopting weird work hours. It was especially difficult having most of the meetings happening in North America and needing to make them from a European timezone. I solved this mostly with co-working spaces and other places outside of home to get work done. I got pretty good at working out of coffee shops but it's not easy. An added bonus of the co-working spaces that discovered was making friends and having some sort of social contact during the workdays.
If you have any other questions feel free to email anytime at the address in my profile.