There's lots to consider and analyze here. But one area of note is that JIRA is already used by many enterprises. But many folks find that despite it's many powerful features, the complexity is crippling. There's a lot to configure. And it's not an easy app to use with all that complexity. This is in stark contrast to Trello, which is essentially a digital agile board. (JIRA has an agile board too, as one of it's many plug and play features.) So if all you need is a simple board and you don't want the heft of JIRA, Trello is great. And now Atlassian can offer that.
The takeaway here is that project management and software tools are inherently complicated by what they have to solve. There's so many different ways to build software and run projects. How do you create the tools to support those workflows so that a new user is not crippled by the complexity? At least in GitLab we are iterating quickly with small improvements every month. But we also have a UX team to design intuitive interfaces and workflows that make sense. We dogfood GitLab ourselves so we understand the pain points (and the complexities!). And of course we develop out in the open to solicit that constant user feedback. As GitLab further matures and we add more features, we are hyper aware that we do not build another JIRA. There is so much configurability and complexity there. It's very heavy. So are iterating quickly, but carefully.
Atlassian now has two products that do the same thing. Jira for the complex cases and Trello for the simple ones.
At GitLab we'll work very hard try to have on product that is pleasant to use for simple cases but still allows you to handle the complex ones.
This is a huge UX challenge but it will allow our users to use a single product for all their needs, so they don't have to move projects between tools when they 'graduate' to the complex one. And it will allow us to ship more features in the single product we work on.
It indeed is hard. I'm happy that we don't have to get it right the first time but that we can iterate. As you've shown with your great work for Jenkins Blue Ocean it is possible to keep improving the simplicity of an interface even for a mature product.
