[dragonwriter]

> For some reason many "enterprise" software products are clunky and buggy.

That's because “selling to enterprises” is a distinct competency from “making a working product”.

> I guess this is because the decision to use the software is made by managers who don't ever use it.

That's, often, an important part of the problem, but another, perhaps more signficant, part of the problem is that enterprise level constraints on software purchasing decisions are often made by managers (or management workgroups with no single responsible party, or even by directly by state or federal legislation and/or regulation from outside the purchasing agency [0]) who are (or, in the case of groups, consist of people who mainly are) remote in time and org-chart distance from both the decision to purchase software and the actual use of the software. This is perhaps most notoriously true in the public sector, where often the most critical competency for selling to an agency is the ability to navigate the acquisition policies applicable to that agency, which in the most complex of cases involve policies driven by both state and federal legislation and regulation by multiple state and federal control agencies as well as the internal policies of the agency actually doing the purchasing, but any large organization tends to have bureaucratic purchasing rules which, while usually well-intentioned and sometimes legitimately necessary to avoid even worse adverse effects, inadvertently reward vendors with competence in navigating the particular bureaucratic maze over those that lack such competence in a way that can at times outweigh competence in delivery.