Pros
Orchard allows me to balance my work against why I'm working: namely, to have a life. I work hard, but the amount of hours I'm expected to put in I find reasonable. Orchard is very low on drama. You don't see much infighting, carping, or the kind of backstabbing I've seen elsewhere. For myself, being the sort of person who works well at a very steady pace and being self-directed, being left to my own devices generally is a key to productivity. The business end of the company is very well-run, and I've seen growth every year since I've been here. The company has never laid off people during my time and the owner has a very genuine sweet spot and affection for the people who work here. Last thing, hard work is rewarded. If you bust your tail and look for chances to contribute and grow your skills, you often see them.
Cons
There are few directions you can move around. Most people start in Support, so the paths out of support are in maybe 6 directions, so if you don't find a home in the limited choices, and you don't get a chance to start something new, you will be stuck answering client support calls indefinitely and eventually managed out. There is still heavy compartmentalization between and tunnel vision within departments: we don't work together between departments very well, though it's improved a lot in the last few years. Finally, there's a bit of a glass wall between managers and non-managers. It seems that once someone does make that management level, the habit is to shift around the deck chairs. Excellence, ambition, and effort aren't enough to break through this. Conversations at the management level don't include the subject experts below that level and seem to happen in a secret room, so if you have a great idea or know the best path, you still may not get the chance to ever relate that.