Ex: if i have a custom field named "Department" (with value Dept 1, Dept 2) and one more custom field named "Users" (with values User 1, User 2, User 3, User 4).
When i select "Dept 1" in "Department" custom field, then "Users" custom field should display User 1 and User 2
When i select "Dept 2" in "Department" custom field, then "Users" custom field should display User 3 and User 4
I do not think the JIRA's default user picker will work for you unless you can predetermine the departments based upon the where you are in the workflow. The groups or project roles need to be predefined.
I believe you might be able to use kepler-romininfo user picker though.
If your JIRA version is before 6.3 there is a free version.
Script runner might work as well
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