My old boss who is working for google now knows ssh. He is 60. But maybe due to he is a member of IETF so he gets updates. I don't think he is in trench. But I think what you described is related to company culture.
Well, to be fair, this guy we're referring to DID come to IBM from the CrossWorlds acquisition. Which, at the time, was a start up. So, I really don't know.