We use JIRA Workflow Toolbox, specifically the "Set a field as a function of other fields" postfunction, to do something similar to what I think you're describing.
You specify the source field (say Region, where values the customer selects are North, South, East, West), and the target field (Assignee), and then you set how the values from the first should write to the second.
(East)=bsmith
(North)=sjones
etc.
As Nic said, you can't assign groups to the assignee field, but if you had a group user custom field, you could use this to set that field too.
What do you mean by multiple transitions? You create an issue. That's it, you can't do anything else, there's nothing to transition until you've got an issue to work with.
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I'm trying to basically assign the issue to different groups depending on a field value entered in the create screen. I want to implement this at the time of creating a work item.
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That has nothing to do with what you asked.
I don't know what you actually want here - to do something with transitions or to do something with group assignee (which you cannot do because assignee must be a single user)
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