It happens any time the buyer isn’t the user. Atlassian products are terrible because some manager buys them and tells everyone they have to use it, and if the engineers complain they’ll probably just blow it off as “they’re too demanding” or “they don’t want to do Agile right”.

It's the incentives that are in place. Most enterprises buy products based on feature sets. Therefore, enterprise software companies prioritize delivering features.

I remember what a friend said about software.

The desktop people want the latest and greatest software ASAP if not sooner.

The server people want nothing to change, ever.

I'm sure enterprise software has similar rules and incentives.

wait until you see medical enterprise software or defense industry enterprise software