You really won't. This isn't mean to be a knock on you, but even the CEO probably can't fix this. Do some research on distruption theory and you'll discover that your company is built to withstand the very kinds of change that you seek. Even a Jedi has to exit when they have no leverage in a given situation.
Also - if you don't already have an overwhelmingly strong picture of what is wrong with blackboard, I'd suggest that your heart isn't invested in improving it, and you might be better off at a company whose software you love.
You won't solve the problem as a software developer. It's not a software problem. Try to climb the ranks into management and weed out corruption as you see it.
Me and other good devs will solve software side of problems, and other good people will fix managerial one :)
Are you saying that everyone in management and engineering had been replaced and Blackboard is essentially a startup which happens to have inherited all the exciting contracts? If so, then maybe you stand a chance.
Otherwise, I'm sure you'll learn a lot from the attempt.
There is a lot of new people indeed (both managers and tech.) Quite a few startups were acquihired too. But I think most important factor - management openly concerned about competition and tries to push toward better product. And it appears to be much better timing too - institutions are more open to "cloud" today, than they were 10 years ago.
I will fix it from inside.