[SalesForce] Drip Campaign with Time-based Workflow

I have set up a simple 'drip email marketing campaign' in Salesforce utilizing a time based workflow.

I added a checkbox to the leads page that reads "Send Drip Emails". There is a workflow that will evaluate and check this box.

Here is a screenshot of the workflow:

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I have another time-based workflow that checks when this checkbox gets checked, and kicks off the workflow. Here is what that workflow looks like:

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For some reason, leads that matched this criteria are not being sent emails. I checked the queue for time based workflows and did not return anything:

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What I am doing wrong?

Also, I added a task to be added so I can see when the email is being sent so that I can see it on the lead record. This is assigned to our sales leader, as I don't think it's possible to assign it to the record owner (person who the email is sent from).

Best Answer

On the field update for your checkbox, did you mark the "re-evaluate workflow Rules after Field Change?"

If that's not marked, your WFR isn't triggering your Time-Based WFR and therefore your emails aren't being sent

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