I think rather than trying to get universities to change from a system they're familiar with, it might be better to focus on software for elementary and high schools. My mother is a teacher at an elementary school, and all their grades, amongst other things, must be done online. The software made me cringe when I saw it. It's all ActiveX, and most of the time it doesn't work. The database on the backend is horribly slow, and it stops working at random intervals. It's also impossible to use if you don't have broadband, and there are still many areas where my parents live where broadband is not yet available.
My mother told me that just before Christmas when their grades were due, she had 18 students to put grades in for (ie, A, B+, C, etc) for 4 subjects. It took her 5 hours because of how slow the system was. This is not a large school system, so they probably had at most 6 people using it at once.
A lot of school systems, especially smaller ones, feel they need to go more digital to "keep up", but their IT people, to put it frankly, are idiots. They spend a lot of money implementing a system that does more harm than good. These are customers that are just starting out, so there is no issue with convincing them to change from their current system like with a university.