It's still overwhelming and complex, so that part has stayed consistent. I imagine it starts with always considering the thing as a product, not as its feature

It's still overwhelming and complex, so that part has stayed consistent. I imagine it starts with always considering the thing as a product, not as its features, so that you can always make sure all the work being done integrates intuitively and intentionally into the original thesis of the product. The very fact that one has to hunt through various layers of oddly organized configuration screens (several of which do almost the same thing), and has to often click on more than one "..." menu to poke around looking for assumed-to-exist functionality before actually finding it, is an indicator that JIRA might be developed as an ongoing train of user stories to create features unmoored from a central thesis. Because if it was developed like a product in total, then its metaphors would be consistent, its language would be consistent, its modes of interaction with those metaphors would be consistent, and intuitive organization would largely fall out of that.