We're currently at 500 users in Jira and it seems the only upgrade option is 2000 users for $14,000.
Is there any way to get an additional 250 users for example?
I'm afraid Atlassian don't offer anything between those two tiers. A long time ago, you could "add" users, but the licences moved to tiers many versions ago, and there is nothing between 500 and 2000. (1000 would be sane and logical, but it's not an option at the moment)
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