From what I recall, David Cutler was quoted in "Showstoppers" about DEC having an engineering culture when he joined but he got discontented after a few years (when his team shipped VMS) because it was too bloated.
Microsoft could be a bit different though. I remember reading from a book that Bill Gates wanted to have PMs control projects, which caused a lot of conflict. I do not remember the timeline, but it must be before Win NT.
So the best bet is to go in early, stay for 5-10 years until the environment starts to rot and you can exercise all of your options, profit, and then jump to the next. The more senior you are, the more control you have, the happier you are. David Cutler is a great example. He did stay in Microsoft but he managed to be a hand-on.