Imported from writer/skills (skills/retention-playbook-generator/SKILL.md). Install upstream with npx skills add writer/skills --skill retention-playbook-generator. Copyright stays with the author.

Retention Playbook Generator

Overview

This skill produces an end-to-end retention playbook covering every stage of the post-acquisition customer lifecycle — from first purchase through advocacy. It specifies exact trigger conditions, communication sequences, channel strategies, offer structures, and success metrics for each lifecycle stage, calibrated to CPG and retail e-commerce purchase dynamics.

When to Use

• Designing or overhauling a retention marketing program
• Building automated lifecycle email/SMS/push workflows
• Improving repeat purchase rate, customer retention, or LTV
• Launching or optimizing a loyalty or rewards program
• Creating win-back and reactivation campaigns
• Establishing retention KPIs and measurement frameworks

Required Inputs

Methodology

Step 1 — Lifecycle Stage Definition

Define the customer lifecycle stages with transition criteria:

New Customer → Developing → Established → VIP → Champion
       ↓            ↓            ↓         ↓
    Lapsed      At Risk      Declining   Dormant → Lost

Step 2 — Stage-Specific Playbook Construction

Stage: New Customer (First 30 Days)

Objective: Drive 2nd purchase; build brand relationship

Flow: Post-Purchase Welcome Series

KPI Targets:

• 2nd purchase rate within 60 days: 30%–40% (consumable CPG), 15%–25% (semi-durable)
• Welcome series email open rate: 50%+
• Subscription conversion (if applicable): 10%–15% of new customers

Stage: Developing Customer (Orders 2–3)

Objective: Build purchase habit; expand basket

Flow: Habit-Building Series

KPI Targets:

• 3rd purchase rate: 55%–65% of those who made 2nd purchase
• Cross-sell acceptance: 15%–20%
• Loyalty enrollment: 40%–50% of 2nd-time buyers

Stage: Established Customer (3+ Orders)

Objective: Maintain cadence; increase AOV and share of wallet

Flow: Relationship Deepening

KPI Targets:

• Annual retention rate: 70%–80%
• AOV growth: 5%–10% YoY
• Category penetration: expand from avg 1.5 to 2.5 categories

Stage: VIP Customer (Top 10%)

Objective: Maximize lifetime value; cultivate advocacy

Flow: VIP Experience

KPI Targets:

• VIP retention rate: 85%–95%
• VIP referral rate: 15%–25%
• VIP AOV premium vs. average: 2×–3×

Stage: At Risk → Lapsed → Dormant

Objective: Prevent churn and reactivate

Flow: Win-Back Ladder

KPI Targets:

• At-risk save rate: 25%–35%
• Lapsed win-back rate: 10%–18%
• Dormant reactivation rate: 3%–8%

Step 3 — Channel Strategy

Define channel orchestration rules:

Email: Primary lifecycle channel; used for all stages

• Frequency cap: 3–4 emails/week maximum
• Personalization: product history, name, preferences, browse behavior
• Best send times: Tuesday–Thursday, 9–11 AM and 7–9 PM local time

SMS: High-urgency, high-value moments

• Frequency cap: 4–6 SMS/month maximum
• Use for: reorder reminders, flash sales, shipping updates, win-back offers
• Always include opt-out; comply with TCPA
• Expected CTR: 15%–25% (significantly higher than email)

Push Notifications: Engagement and real-time triggers

• Use for: price drops on browsed items, back-in-stock, loyalty milestones
• Frequency cap: 1–2/day maximum
• Personalize with product imagery

Direct Mail: High-value moments and premium customers

• Use for: VIP welcome kits, dormant win-back (final attempt), holiday catalogs
• Cost: $2–$5/piece; reserve for LTV > $200 customers
• Expected response rate: 2%–5% (higher than digital for lapsed audiences)

Step 4 — Offer Architecture

Structure offers to protect margin while driving action:

Offer Hierarchy (escalate only as needed):

1. Value-add (no margin impact): Free content, exclusive access, early launch
2. Shipping incentive: Free or expedited shipping ($5–$8 cost)
3. Points bonus: 2× or 3× loyalty points (deferred cost)
4. Percentage discount: 10% → 15% → 20% (escalating ladder)
5. Dollar-off: $10 off $50+ (protects AOV with minimum)
6. Free gift: GWP with purchase (inventory cost, perceived high value)
7. Bundle discount: 15% off curated bundle (AOV protective)

Rules:

• Never lead with maximum discount; always start with value-add
• Cap escalation at 25% off; beyond that, the customer is discount-dependent
• Track discount depth per customer; flag those requiring >15% to convert
• Exclude full-price loyal customers from discount flows (they don't need them)

Step 5 — Measurement Framework

Primary Retention KPIs:

Flow-Level KPIs:

• Open rate, click rate, conversion rate per touchpoint
• Revenue attributed to each lifecycle flow
• Unsubscribe rate per flow (flag if >0.5% per send)
• Time-to-next-purchase after each flow trigger

Output Specification

1. Lifecycle Stage Map: Visual stage definitions with transition criteria
2. Stage Playbooks: For each stage — trigger, flow, touchpoints, content, offers, channels, timing
3. Channel Strategy: Frequency caps, best practices, orchestration rules
4. Offer Architecture: Escalation ladder with margin impact estimates
5. KPI Dashboard: Retention metrics with benchmarks and targets
6. Implementation Roadmap: Phased rollout plan with priority ranking
7. Tech Requirements: ESP/CRM flow configurations, data triggers, integration needs

Examples

Input: "Build a retention playbook for our DTC protein bar brand. Repurchase cycle is 21 days. Current repeat rate is 22% (goal: 35%). We use Klaviyo for email and Attentive for SMS."

Output: Complete 7-stage playbook with Klaviyo flow specifications. Post-purchase sequence with day 0–28 touchpoints driving 2nd purchase. Subscription push at day 14 with "never run out" messaging. Win-back ladder starting at day 42. Implementation roadmap: Phase 1 (weeks 1–2) — post-purchase welcome, Phase 2 (weeks 3–4) — reorder reminders, Phase 3 (weeks 5–6) — win-back flows. Projected repeat rate improvement from 22% to 32% within 90 days based on benchmarks.

Input: "Our skincare brand has high first-purchase-to-second drop-off (70% churn before order 2). Design a retention program focused on the first 60 days."

Output: Intensive first-60-day playbook with 12-touch post-purchase sequence. Day 1: order confirmation with routine-builder content. Day 3: ingredient education video. Day 7: "How's your skin feeling?" check-in with usage tips. Day 14: review request + before/after gallery. Day 21: personalized routine expansion recommendation. Day 30: subscribe & save with 15% off. Day 45: "Results take time" reassurance content. Day 60: reorder nudge with 10% off if no 2nd purchase. Projected: reduce 60-day churn from 70% to 55%.

Guidelines

• The post-purchase-to-second-purchase window is the most critical retention moment; invest disproportionately here
• Different product categories require different timing — don't apply a one-size-fits-all cadence
• Always segment VIPs out of discount flows; they devalue the brand relationship for your best customers
• SMS is powerful but consent-dependent; never assume SMS opt-in
• Measure incrementality of retention programs, not just attributed revenue
• For subscription brands, retention playbook should include pause/skip optimization (not just cancel prevention)
• Direct mail has a resurgence in DTC — use it selectively for high-value moments
• Avoid over-communicating; respect frequency caps aggressively — unsubscribes are irreversible
• Test one variable at a time in lifecycle flows; multi-variable changes make attribution impossible

Validation Checklist

• All lifecycle stages are defined with clear transition criteria
• Each stage has a specified trigger, flow, and touchpoint sequence
• Channel selection is appropriate for each touchpoint with frequency caps
• Offer architecture escalates gradually and protects margin
• KPI targets are set per stage with realistic benchmarks
• Post-purchase to 2nd purchase flow is comprehensive (minimum 6 touchpoints)
• Win-back ladder includes at least 4 escalation steps before sunset
• VIP program includes non-monetary value (access, experience, recognition)
• Implementation is phased with clear priority ordering
• Measurement plan includes incrementality testing approach