Because Atlassian manages to extract boatloads of enterprise money for a product portfolio that can be best described as an inconsistent, unintegrated mess.
Everything they have was bought together and crudely integrated, with each product having totally different ways of using and administrating them. Not to mention that core features (e.g. "merging" duplicate user accounts, SAML login) are paid-for plugins of varying quality. Feature suggestions for the products end up in multi-year-old tickets that one has no way to influence.
But still, enterprises are buying up that crap because the alternatives to JIRA and Confluence plainly suck even more. The only thing that has real competition is Bitbucket, with Gitlab and Github as more than viable alternatives.
Atlassian have very successfully aligned themselves with the managerial layer that like to think their organisations are "agile", or believe that buying some software suite will somehow bring that about, rather than simply codify and entrench their existing faulty workflows and add new processes to bureaucratize.
Agile equals a bunch of complicated "workflows" in Jira. This is a real thing that a non-small number of managers believe. Or if they don't believe it, they sure act like they do.
This came up on the Hadoop JIRA lately. Someone submitted an issue several years ago and the team is investigating it now and he was trying to figure out how to get off the notification list. They ended up having to change the reporter. jfc jira's a mess.
Extracting money is what a business does. They managed to extract enough to get their valuation. It has nothing to do with how bad the product is, and shows why sales is far more important than tech when building a company.
