Claude Skill

Win-back Drafter

Drafts win-back emails for closed-lost prospects. References the original objection and what's actually changed.

Download skill (.zip)Or download whole pack

What it does

Given context about a prospect who passed 6+ months ago, this skill drafts a re-engagement email that acknowledges the original conversation, names what's genuinely different now, and makes a low-friction ask. No "just reconnecting!" energy.

When to use

✓A prospect passed 6+ months ago and something has changed (your product, their situation, the market)
✓You're working through a closed-lost list

When not to use

✗Nothing has actually changed — re-engaging without new info is just spam
✗They explicitly said "never contact us again"

Install

Download the .zip, then unzip into your Claude skills folder.

mkdir -p ~/.claude/skills
unzip ~/Downloads/win-back-drafter.zip -d ~/.claude/skills/

# Restart Claude Code session.
# Skill is now available — Claude will use it when relevant.

SKILL.md

---
name: win-back-drafter
description: Drafts re-engagement emails for closed-lost prospects. References original objection and what's changed.
---

# Win-back Drafter

When the user wants to re-engage a closed-lost prospect, draft an email that acknowledges the previous conversation directly.

## Required input

- **When user last talked** to them
- **Why they didn't buy** — specific reason, not "they passed"
- **What's genuinely different now** — on the user's side (new feature, pricing, proof point) OR on the prospect's side (signal that their situation changed)

If "what's different" is weak or fake, push back. A win-back email without a real reason is the worst kind of cold outreach.

## Output: the email

- Maximum 100 words
- **Line 1**: Acknowledge the previous conversation directly. Don't pretend it's fresh outreach.
- **Line 2**: Reference the specific reason they passed
- **Line 3-4**: What's actually different (concrete, not vague "we've improved")
- **Line 5**: Low-friction ask — 15-min call, NOT a demo
- **Final line**: Graceful out — "If still not relevant, I'll close the loop"

## Tone

Conversational. Like writing to someone you remember. Not "Dear Mr. Smith" formal, not aggressive sales.

## What NOT to do

- "Hope you're doing well" / "It's been a while" — generic
- "Just wanted to reconnect" — that's exactly the energy we're avoiding
- "I noticed you might still be looking..." — fake assumption
- Pretend the previous conversation didn't happen
- Promise vague "improvements" without naming them

## Process

1. Restate the prospect context to confirm you have it right
2. Identify the strongest "what's changed" angle
3. Draft the email
4. Add: "If they reply with [common response], here's how to handle it" — anticipate the next move

Example prompts

Once installed, try these prompts in Claude:

Last conversation was 8 months ago. They passed because we lacked SOC 2. We just got SOC 2 certified. Draft win-back.

Related prompts

Don't want to install a skill? These prompts in /prompts cover similar ground for one-shot use:

sales prompts