In the spirit of my comment a few posts back about enterprise software turning into a loss leader for consumer products, Kragen Sitaker has captured the trouble with enterprise products in pithy and quotable fashion:
Enterprise software is software that gets sold to a so-called enterprise. If you know English well, you might think an “enterprise” is something brave, noble, and dangerous, like starting a small business, but in this case, “enterprise” is used to mean the opposite: it means a large, risk-averse company, whose executives use the term to flatter themselves by pretending that they’re engaged in something brave, noble, and dangerous.
…I didn’t really understand this until KnowNow, the startup I worked at, got turned into an enterprise software company by its VCs and management; although I had previously had the opportunity to observe most of the pieces of the puzzle, I clung to the idea that “enterprise software” was actually technically better in some way from the software I was used to using. It turns out that the differences are entirely social, not technical, and one of the major differences is that “enterprise software” is under much less pressure to have any technical merit.