Over 10 years I have worked at 5 different organisations implementing a variety of different Jira Core/Jira Software implementations, in Cloud, Jira Server, and Jira DataCenter.

There is a common and frustrating problem for all of these organisations which results in a smaller takeup of Atalssian Products, and third part products, and hence a loss a potentially significant loss of revenue to Atlassian.

The problem is that the Jira Licence is at the 'Product' level, and not at the 'Project' level where funding is agreed and accounted for. The Cost Account Managers are Project Managers.. 

Many Project Managers are keen to purchase and take up many more products on offer in order to manage their Projects, and have funding to do so. The problem is that if a Project Manager wants purchase a application, he/she has to fund the entire organisation (at Enterprise Level) which just isn't possible. In other words If a Project wants to Purchase Advanced Roadmaps, Structure, Big Picture (as examples) for his/her Project of 50users, he has to find the money for the entire organsation (perhaps 2000 users or more). It wont happen. This leaves the PM frustrated, and will then look at 'other' tools instead in order to seek a solution (loss of revenue to Atlassian). If the Jira Server, Cloud, Data Center could continue to be licences at enterprise level BUT applications could be licensed at Project level, there would be a huge uptake. Not only tis, there would likely be a domino affect as more an more Project Managers take up this functionality, and other PM's see the benefit from this experience and also take it up. (More revenue for Atlassian).

I have seen this problem at 5 different organisations, and I am sure this is just the tip of the iceberg.