Whenever you do look at a degree, think about a doctorate, especially if there's a direct-to-doctorate option. As long as you don't want to be faculty, it could be an EdD or something similar, doesn't have to be a PhD. It's been my experience, though, that a master's doesn't really do anything for you that a bachelor's doesn't. For the upper level jobs, you really need the doctorate, and for the lower, the bachelor's is fine.
Take it with a grain of salt, perhaps, since I'm faculty, but I'm half-time admin, so I'm starting to see more of that side of things.