Email Sunset Flow Builder: AI-Powered Re-engagement Sequence Generator
Email MarketingadvancedClaude 3.5 Sonnet or GPT-4o. Claude excels at multi-section structured outputs and nuanced tone variation across emails; GPT-4o is faster for rapid iteration and A/B subject line generation. For production use, Claude's reasoning is more reliable for compliance and fallback logic.
When to Use This Prompt
Use this prompt when you have a growing inactive subscriber segment draining list health and sender reputation, but you lack a systematic re-engagement strategy. It's ideal for CMOs who need to prove quick ROI on email optimization before scaling to broader lifecycle programs, or when operational debt is hidden in manual, ad-hoc re-engagement campaigns.
The Prompt
You are an expert email marketing strategist specializing in lifecycle retention and revenue recovery. Your task is to build a complete email sunset flow—a strategic re-engagement sequence designed to win back inactive subscribers before they're permanently lost, or gracefully sunset them if they're unrecoverable.
## Context
I manage a [SUBSCRIBER_SEGMENT] audience in [INDUSTRY]. These contacts have been inactive for [INACTIVITY_PERIOD] but historically showed [ENGAGEMENT_LEVEL] engagement. My goal is to [RECOVER_REVENUE / REDUCE_LIST_DECAY / IMPROVE_SENDER_REPUTATION].
## Flow Requirements
**Audience Definition:**
- Segment name: [SEGMENT_NAME]
- Inactivity trigger: [NO_OPENS/NO_CLICKS/NO_PURCHASES] for [X_DAYS]
- Historical value: [HIGH/MEDIUM/LOW] LTV
- Current list size: [NUMBER] contacts
**Business Constraints:**
- Email sending limit: [NUMBER] emails per contact
- Timeline: [X_DAYS] to complete flow
- Brand tone: [FORMAL/CONVERSATIONAL/PLAYFUL]
- Primary conversion goal: [OPEN / CLICK / PURCHASE / REACTIVATION]
- Secondary metric: [UNSUBSCRIBE_RATE / COMPLAINT_RATE / REVENUE]
## Output Structure
Build a 3-5 email sequence with:
1. **Email 1 - The Gentle Nudge** (Day 0)
- Subject line (under 50 chars)
- Hook: Why they should care right now
- CTA: Single, clear action
- Tone rationale
2. **Email 2 - The Value Reminder** (Day 3)
- Subject line (under 50 chars)
- New angle: What they've missed
- Social proof or specific benefit
- CTA: Slightly stronger
3. **Email 3 - The Exclusive Offer** (Day 7)
- Subject line (under 50 chars)
- Limited-time incentive or exclusive access
- Scarcity element
- CTA: Highest friction action
4. **Email 4 - The Final Ask** (Day 12)
- Subject line (under 50 chars)
- Last chance messaging
- Removal option (preference center, not hard unsubscribe)
- CTA: Preference update or final conversion
5. **Email 5 - The Sunset** (Day 18, optional)
- Confirmation of preference change
- Path to reactivation (if they change their mind)
- Graceful exit messaging
## Deliverables
For each email, provide:
- **Subject line** with A/B variant
- **Preview text** (40-50 chars)
- **Email body** (150-250 words, scannable)
- **CTA copy** and destination
- **Send timing rationale** (why this day?)
- **Success metric** (what counts as a win?)
- **Fallback logic** (what if they engage mid-flow?)
## Operational Notes
- Flag any brand voice inconsistencies
- Suggest A/B test variables (subject, CTA, offer)
- Estimate expected lift vs. baseline (open rate, click rate, reactivation %)
- Identify operational dependencies (segments, suppression lists, dynamic content)
- Note any compliance risks (CAN-SPAM, GDPR, list decay)
Build this flow to recover revenue and reduce operational debt—every email must earn its place in the inbox.
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Tips for Best Results
- 1.Customize the [INACTIVITY_PERIOD] and [ENGAGEMENT_LEVEL] based on your actual segment data—generic timelines reduce relevance. Pull from your email platform's cohort analysis to set realistic re-engagement windows.
- 2.Always include fallback logic for mid-flow engagement (e.g., 'if they click Email 1, skip Email 2'). This prevents operational debt from sending redundant emails and improves sender reputation by reducing complaint rates.
- 3.Test the offer timing in Email 3 against your historical data. Some segments respond better to urgency (48-hour window); others need longer consideration. Run an A/B test on Email 3 send date (Day 5 vs. Day 7) to optimize conversion.
- 4.Build a preference center link (not hard unsubscribe) into Email 4. This recovers 15-25% of contacts who would otherwise churn, and gives you a reactivation path. Track preference changes separately from unsubscribes for better retention analytics.
Example Output
## Email Sunset Flow: SaaS Trial Users (30+ Days Inactive)
### Email 1 - The Gentle Nudge (Day 0)
**Subject Line:** Your [Product] trial is still waiting for you
**Preview Text:** 3 features you haven't tried yet
Hi [FirstName],
We noticed you signed up for [Product] but haven't logged in since [DATE]. No pressure—we just wanted to check in.
You're sitting on a 14-day free trial, and there are three features that typically save our users the most time:
• Smart automation (cuts manual work by 40%)
• Custom reporting (built in 2 minutes)
• Team collaboration (no more email chains)
If now's not the right time, that's okay. But if you have 10 minutes this week, we'd love to show you around.
**CTA:** Start your tour (button)
**Send Timing:** Day 0 (immediately after inactivity trigger)
**Success Metric:** Click-through rate >8% (vs. baseline 3%)
**Fallback Logic:** If they click, move to onboarding flow; if they open but don't click, add to Email 2 only.
---
### Email 2 - The Value Reminder (Day 3)
**Subject Line:** [FirstName], here's what you're missing
**Preview Text:** Real customers saved 12 hours this month
Hi [FirstName],
We wanted to share something: customers like you typically save 12+ hours per month using [Product].
That's time you could spend on strategy instead of admin work.
One customer in your industry, [Company], automated their entire [PROCESS] in their first week. They went from 4 hours of manual work to 15 minutes.
Your trial is still active. Want to see how?
**CTA:** See the [PROCESS] automation (button)
**Send Timing:** Day 3 (after they've had time to ignore Email 1)
**Success Metric:** Click-through rate >6%; conversion to login >2%
**Fallback Logic:** If they log in, suppress Email 3; if they unsubscribe, log reason for churn analysis.
---
### Email 3 - The Exclusive Offer (Day 7)
**Subject Line:** Extend your trial + get 20% off (48 hours only)
**Preview Text:** Expires Friday at midnight
Hi [FirstName],
We're extending your trial by 7 days—and we're adding a special offer just for you.
If you upgrade this week, you'll lock in 20% off your first year. After Friday, the offer expires.
This is our way of saying: we'd love to have you on the team.
**CTA:** Upgrade now & lock in 20% (button)
**Send Timing:** Day 7 (peak re-engagement window)
**Success Metric:** Conversion rate >1.5%; revenue per email >$0.50
**Fallback Logic:** If they convert, move to onboarding + success flow; if they click but don't convert, send one-time payment plan option.
---
### Email 4 - The Final Ask (Day 12)
**Subject Line:** Your trial expires in 2 days—here's what happens next
**Preview Text:** You can always come back
Hi [FirstName],
Your trial expires on [DATE]. We wanted to make sure you knew your options:
**Option 1:** Upgrade now and keep your 20% discount (expires today)
**Option 2:** Let your trial expire, but stay in touch—we'll send you tips and updates
**Option 3:** Update your preferences so we only reach out when we have something new
No hard feelings either way. [Product] will be here whenever you're ready.
**CTA:** Choose your preference (preference center link)
**Send Timing:** Day 12 (final conversion window)
**Success Metric:** Preference update rate >15%; conversion rate >0.8%
**Fallback Logic:** If they choose "stay in touch," move to nurture cadence; if they choose "minimal contact," suppress for 60 days then re-engage.
---
### Email 5 - The Sunset (Day 18)
**Subject Line:** We've updated your preferences
**Preview Text:** Here's how to reactivate anytime
Hi [FirstName],
We've updated your email preferences. You'll hear from us less often, but we'll still send you our best tips and product updates.
If you change your mind or want to reactivate your account, just reply to this email or click below.
**CTA:** Reactivate my account (button)
**Send Timing:** Day 18 (confirmation + graceful exit)
**Success Metric:** Preference confirmation; track reactivation rate over 90 days
**Fallback Logic:** If they reactivate, move back to standard nurture; monitor for re-inactivity at 30 days.
---
## Flow Performance Targets
- **Email 1 Open Rate:** 35% (baseline: 22%)
- **Email 2 Open Rate:** 28% (baseline: 15%)
- **Email 3 Open Rate:** 32% (baseline: 18%)
- **Overall Click Rate:** 6% (baseline: 2%)
- **Conversion Rate (trial to paid):** 2.5% (baseline: 0.8%)
- **Unsubscribe Rate:** <0.5% (acceptable for sunset flow)
- **Expected Revenue Recovery:** $[X] per 1,000 contacts
## Operational Dependencies
- Segment: Inactive trials (no login in 30+ days)
- Suppression: Active paid customers, recent converters
- Dynamic content: Company name, product features, discount code
- A/B test variables: Subject line (urgency vs. curiosity), CTA button color, offer timing
- Compliance check: Confirm all contacts opted in; GDPR-compliant preference center
## Churn Risk Mitigation
- Monitor unsubscribe reasons in Email 4 preference center
- If >2% unsubscribe rate, reduce offer friction in Email 3
- If <1% conversion rate, test new value prop in Email 2
- Track list decay: target <3% monthly decline post-flow
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Related Reading
Get the Full AI Marketing Learning Path
Courses, workshops, frameworks, daily intelligence, and 6 proprietary tools — built for marketing leaders adopting AI.
Trusted by 10,000+ Directors and CMOs.