Wake the Dead Play: Reactivate Closed-Lost Deals - The GTM with Clay Blog

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The Wake the Dead Play: Reactivate Closed-Lost Deals with Clay

Author

Author

Jacob Tuwiner

Date

Apr 18, 2026

‍ 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:

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

Here's exactly how I did it:

TL;DR

How to Run the Wake the Dead Sales Play

Bring Closed Lost Deals Back to Life (Wake the Dead Play) - YouTube

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Bring Closed Lost Deals Back to Life (Wake the Dead Play) Jacob Tuwiner | AI Sales Automation

Jacob Tuwiner | AI Sales Automation3.7K subscribers

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

  2. Full Name

  3. Work Email

  4. Company Name

  5. Opportunity Owner (the AE who owned the deal)

  6. Deal Closed Date (when the deal was lost)

  7. Call Notes (the initial reason the prospect was interested)

  8. 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:

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

  2. Check if they're still at the company (if not they go into other sequence)

  3. Use ChatGPT + CRM notes to create following outputs:

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.

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 😉

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:

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!

[Bonus] Email Template

-> Swipe the play email copy here.

Table template coming soon!

‍

Frequently Asked Questions

What is the wake the dead play?

It's a sales reactivation play that uses Clay, ChatGPT, and CRM notes to send fully automated, personalized emails to closed-lost prospects. The goal is to restart conversations with deals that went cold, using context from the original deal to make the outreach feel relevant.

How far back should I go when pulling closed-lost deals?

The play recommends exporting deals lost in the past 1-2 years. Going further back risks reaching contacts who have moved on or whose context is too stale to personalize effectively.

What CRM fields do I need for this to work?

You need prospect name, work email, company name, opportunity owner, deal closed date, call notes (why the prospect was originally interested), and the deal lost reason. These fields feed the ChatGPT personalization step.

What happens if the contact has left the company?

The Clay workflow checks whether the contact is still at the company. If they've left, they get routed into a separate sequence rather than receiving the standard reactivation email.

What email tool is used to send the sequence?

The post uses Instantly to upload the personalized CSV and schedule the email sequence. The personalized variables are exported from Clay as a CSV and mapped into the Instantly email template.

Index

How to Run the Wake the Dead Sales Play

1. Export closed-lost deals from your CRM

2. Import key info about the lost deals into Clay

3. Personalize variables w/ ChatGPT + CRM info

4. Export personalized variables for email template

5. Upload into Instantly and schedule sequence

[Bonus] Email Template

Frequently Asked Questions

What is the wake the dead play?

How far back should I go when pulling closed-lost deals?

What CRM fields do I need for this to work?

What happens if the contact has left the company?

What email tool is used to send the sequence?