I was retired before I transitioned, so I have no direct experience of being employed during transition. But like so many of our sisters, I was in IT for most of my career.
The last six years of my career were spent working from home. Had I been ready to transition, it would have been no problem. I didn't even see my boss or co-workers for that entire period. Before that, I worked in a downtown office, so I would have been visible, but IT people really only care about the work that you do. I do not think I would have had any problems transitioning at that workplace.