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Stale Deal Re-Warming

Example prompt: "Find all deals in HubSpot with no logged activity in 10 days. Send a friendly check-in email to the contact and alert the sales manager on Slack."

How to automate stale deal rewarming with GloriaMundo

The Problem

Deals go quiet. A prospect stops replying, a rep gets busy with hotter leads, and suddenly there are a dozen open deals in the pipeline with no activity logged in the past week or two. These are not necessarily lost — many just need a nudge. But identifying stale deals means running filtered CRM reports, and writing individual follow-up emails for each one takes time that reps would rather spend on active opportunities. The result is that winnable deals slip through the cracks, and pipeline reports overstate the real value of open opportunities.

How GloriaMundo Solves It

We build a scheduled workflow that runs daily (or weekly). An integration step queries HubSpot for all open deals where the last logged activity is older than a configurable threshold — say, 10 days. For each stale deal, an LLM step drafts a short, friendly check-in email tailored to the deal context: it references the deal name, the last conversation topic, and asks a low-pressure question to re-engage. A conditional step filters out any deals already in a closing stage (to avoid awkward nudges on deals that are just waiting on contracts). The drafted emails are saved as Gmail drafts for the rep to review, or sent directly if you prefer. A summary of all stale deals and actions taken is posted to a Slack channel so the sales manager has visibility. Glass Box preview shows you the stale deal list and draft emails before anything is sent.

Example Workflow Steps

  1. Trigger (scheduled): Runs every weekday morning at 9am.
  2. Step 1 (integration): Query HubSpot for open deals with no logged activity in the past 10 days.
  3. Step 2 (conditional): Filter out deals in closing stages (e.g., "Contract Sent", "Closed Won") to avoid unnecessary follow-ups.
  4. Step 3 (LLM): For each remaining stale deal, draft a brief check-in email referencing the deal context and last known conversation topic.
  5. Step 4 (integration): Save each draft email in Gmail for the rep to review and send.
  6. Step 5 (integration): Post a summary to a Slack channel — list of stale deals, days inactive, and actions taken — so the sales manager can follow up.

Integrations Used

  • HubSpot — source of deal data and activity history
  • Gmail — where check-in email drafts are saved for rep review
  • Slack — summary alert channel for the sales manager

Who This Is For

Sales managers and account executives who want to make sure no open deal goes unattended for too long. Especially useful for teams with 20+ active deals per rep, where it is easy to lose track of which prospects have gone quiet.

Time & Cost Saved

Manually auditing the pipeline for stale deals and writing follow-up emails takes roughly 30-45 minutes per day for a diligent rep. This workflow automates the identification and drafting, reducing the effort to a quick review of pre-written emails — around 10 minutes. Over a month, that is 7-12 hours saved per rep. More importantly, re-engaged deals that would otherwise have been forgotten represent recovered pipeline value that is difficult to quantify but often significant.