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Wake The Dead 🧟‍♂️ : Turn Stalled Opportunities into Won Deals

Wake The Dead 🧟‍♂️ : Turn Stalled Opportunities into Won Deals
Jacob Tuwiner
Wake The Dead 🧟‍♂️ : Turn Stalled Opportunities into Won Deals
Wake The Dead 🧟‍♂️ : Turn Stalled Opportunities into Won Deals

Most follow-up emails don’t wake the dead…(the dead = prospects that never made it through your pipeline)

This play uses Clay to send automated emails (personalized w/ ChatGPT + CRM notes) to restart conversations with closed-lost prospects.

100% automated emails SO GOOD — they get results like:

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All of these sequences were 100% automated using Clay + ChatGPT + CRM notes.

Here’s exactly how I did it:


  1. Create list of closed-lost opportunities from past few years (export from Salesforce/HubSpot)
  1. Pull key deal info into Clay table (prospect name/email, when the deal was lost, deal notes, etc)
  1. Use ChatGPT to personalize email based on CRM info (see below):
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How to Run the “Wake The Dead” Play

1. Export closed-lost deals from your CRM

Find all of the deals that were were lost in the past 1-2 years and export them as a CSV.

(If you need more help — just ask ChatGPT)

Make sure to include the following info in the export:

  1. Prospect/Contact Info
  1. Full Name
  2. Work Email
  3. Company Name
  1. Opportunity Owner (the AE who owned the deal)
  1. Deal Closed Date (when the deal was lost)
  1. Call Notes (the initial reason the prospect was interested)
  1. Deal Lost Reason (the noted reason for losing the deal)

2. Import key info about the lost deals into Clay

Create a new table in Clay, click “Import People From CSV”, and upload the CSV from step 1:

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3. Personalize variables w/ ChatGPT + CRM info

General steps to create the personalized outputs used in the email:

  1. Check if the email is valid
  1. Check if they’re still at the company (if not they go into other sequence)
  1. Use ChatGPT + CRM notes to create following outputs:
  • Months Ago (created from the date when the deal was closed + normalized)
  • Context Output (created from the CRM call notes)


4. Export personalized variables for email template

After creating all of the personalized outputs — I add them to a “final output” view in Clay and export the view as a CSV.

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See how the CSV outputs are used in the email template below?

“because because” was a mistake - but small mistakes make it feel more human 😉
“because because” was a mistake - but small mistakes make it feel more human 😉

5. Upload into Instantly and schedule sequence


After a few days if they don’t respond — I ask them if another contact in their company (found using the find contact integration) is a better point of contact.


If it wasn’t able to find another contact (who fits specific requirements) it uses “someone else” as a fallback. You’d be surprised by how effective this last little email is haha. Especially since I say “Wine or cookies are stills yours :)”  

…and that’s how I was able to get these kind of results with 100% automated emails:

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Pretty neat, yea?

Appreciate you reading all of this!

If you got any value from it do me a quick favor and share it with someone. The exposure helps my business. Cheers!

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[Bonus] Email Template

-> Swipe the play email copy here.

Table template coming soon!

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A product mockup of a table with columns showing imported LinkedIn contacts and enrichments from different marketing/outbound tools
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