It's extremely hard to break into because like healthcare these gigantic institutions where nobody can get fired made choices ten to twenty years ago that have now become "the way it's done" and they won't accept a better solution.

I know. I am at one of those institutions. We practically have a social sciences lab for the Dunning-Kruger effect in place of IT decision makers.

In fairness, my university changed systems every year or so while I was there. They all sucked, so sticking with your existing solution is possibly not the worst decision.

Blackboard is a known aggressor with its patent portfolio and cash. They will acquire and extinguish or just kill you with a patent lawsuit if you present a significant threat to their products.