Stalled Opportunity Playbook: How to Revive Lost Deals in Your CRM

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Your CRM is full of ghosts. Closed/Lost opps, no-decisions, and buyers who said “circle back in Q3” but never heard from you again.

Most of these deals didn’t die because of bad fit. They stalled because of timing, priorities, or bandwidth. The problem is, reps rarely go back to revive them.

This playbook shows you how to revive lost deals and even how to systematise it.

Why Stalled Opportunities Are Worth Another Look

Deals stall for reasons that have nothing to do with fit:

• Budget freezes push buying decisions out a quarter or two.
• Leadership changes reset priorities and delay projects.
• Lost momentum turns initial enthusiasm into silence.

If you only chase net-new prospects, you’re ignoring buyers who already know your product, already took a meeting, and already showed intent.

Re-engaging them is often easier than breaking into a new account.

Step 1: Audit Your CRM

If you're doing this yourself, you want to start with auditing your CRM.

• Pull reports of Closed/Lost deals from the past 6–12 months
• Filter out the “bad fit” accounts and try to isolate opportunities that were lost for reasons like budget freeze or wrong timing.

You can put this into a spreadsheet.

How to systematize this:

Stalled and closed/lost deals are automatically flagged live in Letterdrop. This includes information like reason for stall and the relevant contact.

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Step 2: Review Old Sales Calls

You want to make sure you know why the deal was stalled and when to reach out again.

To do this, you need to sift through call transcripts from tools like Gong or Chorus.

This needs to be flagged in a spreadsheet and even in your CRM itself.

How to systematize this:

AI automatically mines your call transcripts for these reasons and attaches them to the Revive Deals dashboard in Letterdrop.

You even get direct quotes from the prospect.

Step 3: Reach Out

Going back to your spreadsheet, you need to draft emails and DMs at the right time to re-engage your stalled ops.

Using a reminder system (like on your calendar) goes a long way here, as long as you're diligent.

Good examples of messages are:

“Back in April, you mentioned budget freeing up in January. Are you evaluating now?”

“Saw your new VP Marketing started last month. Often priorities reset with new leadership, worth reconnecting?”

How to systematize this:

Outreach drafts itself in Letterdrop. You just need to push it through your outbound system (Apollo, Outreach, etc.) This can be set up in our Workflows.

Reps are messaged via Slack and email accordingly so you know when to reach out, based on what the prospect said.

You can set up approval systems as well as a fallback contact.

Make Reviving Deals Automatic

Your team already put in the work to create those opportunities. The only question is whether you’ll let them rot in the CRM or bring them back at the right moment.

Put reviving them on autopilot so your reps don't need to lift a finger.