Hello @tboardman, I hope you are doing well today. I understand how helpful it would be for you if we can trigger multiple webhooks from one single automation rule. A few of our other customers have also written to us regarding the same in the past and I’d like to confirm this has been raised as a feature request to our product team. 

As of now, we can add only a webhook per rule but you can have different matching conditions to trigger another webhook in a separate rule.     

That said, we’ll be sure to keep you posted with updates in the furture.