What you have in most education software is that they're catering to the decision-maker who makes the budget allocations and that decision-maker has a lot of check boxes. Does it do this? Check. Does it do that? Check. They could care less about the end user experience.
I've been very very lucky in my career in my life - from day one. When aspiring directors say 'What's your advice?' first I say 'Be born the son of a famous director. It's invaluable.'