Ask HN: Obstacles to entering the B2B market?

One of my ideas for a startup is as follows: A student course registration application univerisities would use that would help students choose and register for the right classes for their degree plan. the current state of these apps (from what I've seen at Texas A&M and Texas Tech) could use some improvement.

My concern: The industry of enterprise software seems pretty buddy-buddy, and I wouldn't know where to start in demoing and selling the application.

Have any other HN'ers faced unique challenges posed by barrier to entry in a B2B market?