Ask YC: Avoiding "enterprise software" and self-justifying IT groups?

One of the things I miss most about working at a startup is that IT in a startup focuses on actual productivity. Ironically, in a tiny company with a keen instinct for survival, the IT people at a startup don't seem as paranoid as those in large companies. There's no "herd" making things needlessly difficult. And certainly no zealots who believe the only conceivable way to solve a problem is by paying (horrible) software companies millions in licenses. There's no automatic disdain for free or open-source software, either.

What would you do to transform a larger company? To challenge them to take a risk and try to get the job done without Microsoft? To instill in people the importance of proper research (e.g. don't pay thousands for a helpdesk when there are dozens of free ticketing systems)? To reassure them that "invisible", highly effective systems are productive and won't cause IT people to be fired?