I think this gets it wrong. The real reason enterprise software sucks is that enterprises have complex and unique workflows and would prefer to buy software that they can fit to their workflow rather than change the workflows of their profitable business with tens of thousands of staff who will need retraining. If you look at all of the most successful software of all time they are the complete antithesis of the Unix…
Existing users' familiarity with existing tools and the ability to accomplish existing tasks with existing skills are all part of the competitive landscape for any tool that must compete for people who use it by choice. In other words, if the user chooses the tool, they will choose a tool that allows them to accomplish what is necessary, given their existing skills. That this choice is so often lacking is just a symptom of the reduction of individual agency in the modern corporation. There is no fundamental law preventing software from becoming more usable and more powerful over time.
In fact, for as often as enterprise procurement keeps old interfaces around longer than they should be, it is just as often responsible for replacing something that everyone knew how to use with something worse, rendering institutional knowledge worthless overnight.
> most successful software of all time
By what definition of success?
> People hate them because they are complex, configurable, and have 1000 features.
> But that's the same reason they can [meet the need.]
Good design is precisely about enabling complex work with well-chosen, simple yet powerful tools. Your statement implies or at least suggests that any tool that meets a complex set of business needs must be something people hate, which is equivalent to saying that well-designed tools cannot exist -- equivalent to giving up on design.
All the evidence shows us is that good design is rare, and much more so whenever tool users are not tool choosers.
If you believe good design is possible (as you suggest later, that it is just expensive) then what you're saying is simply that bad design is cheaper, and is the default outcome when good design is not valued, all of which is certainly true. However, you still have to explain why good design fails to thrive in the market, and why large numbers of people are using trash tools that everyone hates and no-one could ever love.
This may be explained by the principal-agent problem, by network effects, as in the case of platforms and productivity tools, by a lack of user awareness, or various other reasons, but simply saying that good design costs and doesn't happen by accident is not a sufficient explanation for what we see happening in the market. You might believe that the market is correct here, and good design simply isn't worth the cost, but it wasn't clear to me if that's your position.
> That the end user isn't the purchaser isn't going to change that fundamental reality that businesses are complicated.
The fundamental reality here is that good design will only be rewarded when the people who suffer from bad design are empowered to choose otherwise. As long as the cost of good design is borne by party A, while the pain of bad design is borne by party B, and party A pays for and chooses the tools, then bad design will continue to dominate.