Managing Director isn't exactly as high up in the chain at MS as it sounds and he could definitely still be getting his hands dirty directly with technical decisions at that level. When I worked there I worked with one MD who was 3rd in line on the pager list and was more than comfortable logging into the servers to resolve problems if there was an issue that for some reason 1st and 2nd level weren't in a position to respond to.

Edit: I got MD/ED backwards. Ignore the above.