I wouldn't say Headmaster is more serious (been playing for years, and the humor is viciously dry with a nice dose of cynicism, which is why I love it). Only in the early stages of this game right now, but so far the uniform styles seem to to be the biggest similarity.
If I had a gripe, it would be with Itch. The "similar games" engines is a massive disgrace. As is the inability to search games by name and still not have them come up.
I'd also point out the limited number of scenarios where the concept works.