I worked in academia for quite a few years. This is an industry that could really use disrupting, but I'm incredibly cynical about the possibilities of this ever happening (as far as changing internal software). Just about anyone on HN could write a better lms than blackboard, and sell it for 1/100 of the cost for huge profit margins (okay maybe some exaggeration here, but not much). But blackboard is not unique, alm…
Is there really a university IT department out there that's going to prevent students and professors from using an offsite, external website? Especially if it's keeping professors happy (who, let's face it, probably complain a lot about IT's offerings) and doesn't cost them anything? Coursekit in its current form isn't dependent on IT for anything -- they host on their own server, use their own logins. IT can either ban it (and face the whiplash), or politely ask the tenured professors to stop using it (and they wouldn't even know which professors are using it, since it's external). The one thing they could kick up a storm about is student grades being stored on an external server. That's a pickle.
Faculty won't pay for this, true -- thankfully, there are other ways to make money in the industry -- but a much bigger problem is that faculty aren't even looking for it. They've been conditioned that software comes from IT, so while they may hate using Blackboard, most aren't googling for "Blackboard alternatives". That'll need to change. I think Coursekit's strategy of creating student evangelists might actually work though, especially at smaller schools where the relationships between students and professors is stronger.