Stale Deal Alert with Re-Engagement Recommendation

Automatically identify deals that have had no activity for a defined number of days and send the rep an alert with an AI-generated re-engagement recommendation. Prevents deals from dying silently in the pipeline without a rep noticing until it's too late.

Trigger: Scheduled daily or weekly check (e.g., every Monday at 8am)

Steps:

  1. Scheduled trigger queries CRM for all open opportunities with last activity older than [X] days
  2. For each stale deal, pull: account name, stage, value, last activity, champion name
  3. Send to AI API: "This deal has been stale for [X] days. Given the stage and what you know, what is the single best re-engagement move?"
  4. Send rep a Slack or Teams alert with deal name, days stale, and AI recommendation
  5. Optionally: create a CRM task for the rep with the recommended action

Tools: Zapier or Power Automate, Claude API, HubSpot or Salesforce or Dynamics 365, Slack or Teams