Hi @slohberg ,
welcome to the Atlassian Community!
I worked with webhooks several times, but I didn't find any way, how to do it. Maybe others were more successful...
In the past I've handled it like this - when the request was successful, external WebService sends Jira some sort of notification using Jira REST API (write comment to issue, update some custom field...). But this is not very good solution.
I started to use Send web request action in Automation for Jira instead of webhooks recently, because it provides more functionality (response data, audit log...).
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