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Win back closed-lost deals with one honest email per stakeholder
Picked and checked by Olga Pearson, SalesUpLevel
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Reported: "I've closed $1,556,541 (thanks Claude), from deals I had initially lost ... ~16 months from closed lost to eventually take the customer to closed won but that's ~300K per year (for every year I've been at Clozd)".
Go back through calls on deals you lost, pull the problem each person described in their own words, and send each stakeholder a short, personal note asking if it ever got solved. No pitch.
By Austen Schaefer, Enterprise Account Executive III, Clozd · Austen Schaefer on LinkedIn ↗ · Sep 25, 2026
If you sell: run it before your 10am
- List your closed-lost deals from the past 6 to 18 months.
- For each, pull the call notes or transcripts (his: Gong) and note each stakeholder's problem in their words.
- Paste the notes into Claude with the prompt below.
- Edit each email so it sounds like you, then send one per stakeholder.
- Log replies and set a reminder to check back on the "still a problem" ones.
I'm re-engaging a deal I marked Closed Lost. My call notes are below. Write a separate short email to each stakeholder that: Opens by acknowledging what was going on in their world when we last spoke Reminds them of the specific problem they described, in their own words Asks one honest question: did it get solved, or is it still a problem? Mentions any other project they brought up, without pushing Ends with "No agenda here" and an easy way to say nothing's changed Rules: under 150 words, no pitch, no "just circling back," no attachments. It should sound like a person, not a sequence. Subject line: "Checking back in — still thinking about [Company]" Context: Stakeholders: [names + titles] Last spoke: [month/year] Why we lost: [competitor / no decision / budget / unknown]
If you lead a team: roll it out
- Make a quarterly closed-lost win-back hour part of every AE's calendar.
Watch out for
- The $1.56M is cumulative over his years at Clozd, with about 16 months from lost to won, so this is slow money.
- The prompt is quoted exactly (it has a dash in the subject line; change it if you like).
- Paste only call notes your company allows in AI tools.
Source: Austen Schaefer, Austen Schaefer on LinkedIn, Sep 25, 2026. Results are as reported by the source; we did not measure them.
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