There is a scale where things like jira make sense, but much like cloud services it's a technical trap because by the time you realize the tool doesn't really work for your use case it's too late to switch.

Heh, my org went the opposite route. They started by developing their own tool that's gotten so big and bloated (with all the original implementers LONG gone) that it's at the point where they're talking about moving to a pre built tool because the self built one is too unwieldy to do what we need to do.

At that point you're already past the point you need to start developing your own tool, but the sunk cost fallacy is a bitch and there's never enough funding for that.

And if you're not at that point at the beginning of the process, wait a few years until employee churn is high enough that the sunk cost of the self built system is finally outweighed by the technical debt of the system.