For instance, we have multiple contractors working with us and we need a way to break down how many licenses are being used by each contracting company. I would think that there are a few different ways to do this. I would tend to lean toward groovy script but I wouldn't know where to start writing that since my scripting skills are week at best. This would apply for both Confluence and JIRA.
Use the "Groups" feature in JIRA to group users. Just any script/code that can call the JIRA REST API and add those certain users to their particular group.
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