Retention emails are higher-leverage than acquisition emails because the audience already pays you. Most B2B teams underinvest because the per-segment customization is hard to scale. AI changes that. Here are the 3 sequence types and the prompts.
1. Renewal nurture (60-90 days before renewal). Reinforce value before the decision moment.
2. Expansion outreach. Trigger when usage signals warrant additional product.
3. Win-back. Targeted re-engagement for churned customers.
Build a 60-day renewal nurture sequence for [CUSTOMER NAME]. Customer plan: [TIER] Renewal date: [DATE] Their original use case (from sales): [SHORT] Their usage pattern: [HEAVY / MODERATE / LOW USE] Their last 6 months of engagement: [SUMMARY] Key wins they achieved: [LIST] Key friction they experienced: [LIST IF KNOWN] 3-touch sequence over 60 days: - Day -60: ROI reminder — specific numbers showing what they got - Day -30: Strategic check-in — what we could do together next year - Day -7: Renewal confirmation + any negotiation flag For each email: - Subject line (specific, not "Your renewal is coming up") - Body (150-200 words) - Single CTA per email - Personal tone — this is a relationship, not a campaign The arc moves from "remember what you got" to "here is what is next" to "let us make this easy."
Build a win-back sequence for a customer who churned [N MONTHS AGO]. Why they churned (stated reason): [REASON] Why they REALLY churned (your honest assessment): [HONEST] What has changed about our product since they left: [LIST] What has changed about their business that we know of: [LIST IF KNOWN] 3-touch sequence over 60 days: - Touch 1: "We have changed" — honest reference to the original reason, specific changes we have made - Touch 2: Insight piece — relevant content with no pitch - Touch 3: Specific offer — low-friction re-engagement For each email: - Acknowledge the past honestly (do not pretend they were not a customer) - Lead with what changed, not what they should buy again - Offer 1 specific easy next step (audit, call, free trial of a new module) - Max 150 words Voice: humble, specific, not pushy. They left for a reason. Earn the second chance.