How to mark a flag for no customer interaction for more than 3 weeks

We have a page in Confluence, which has the list of our customers. Every customer is linked to a JIRA item as a client. For customers who have not responded for more than 3 weeks, this has to be escalated to our management. Is there a way, I can have a flag added and trigger an email to management for further action??

Appreciate any response.

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