I heard Cem Kaner say once that software has the "cat food problem." The people buying it don't consume it, so the quality is low.
I think that sums up the enterprise space well. It's all bought by people who are not using it and want to be as hands off as possible. That is the core problem - you have to look good on paper (read: big feature list) to get attention. It's a space for heavily-bankrolled startups or people who are creatively repurposing existing software. Mostly the latter.
I'm finding more and more this isn't the case (I agree with you that it definitely has been that way in the past though).
More and more business people are tech savvy enough to know what they want nowadays, they might get IT in to do some initial work (vendor screening etc), but any real business impacting decisions are made by the people who use/benefit directly from the software investment, unless of course you're selling IT management software to IT departments.
I think that sums up the enterprise space well. It's all bought by people who are not using it and want to be as hands off as possible. That is the core problem - you have to look good on paper (read: big feature list) to get attention. It's a space for heavily-bankrolled startups or people who are creatively repurposing existing software. Mostly the latter.