A friend recently tried to go for a github enterprise install at his >$1B market cap company. He really wanted it, they made it hard.

Some specific gripes included very slow support response time and poor options for installs (vm based only). There were others but it boiled down to the ops guys asked to set up and maintain the system weren't happy with the way they were treated.

I don't think 'going enterprise' is good for the culture of any company, but if they want to do it, they definitely have to kick up their game.