reaperinvest Customer Success Playbook
When to Use This Skill
Use this skill when you need to:
- Design a proactive customer success program with defined touchpoints
- Map the customer lifecycle from onboarding through renewal and expansion
- Create playbooks for common scenarios (new customer, at-risk, expansion-ready)
- Standardize how you nurture and retain customers long-term
DO NOT use this skill for customer onboarding flows (use onboarding-flow), support templates, or sales processes. This is for the ongoing success strategy across the full customer lifecycle.
Core Principle
CUSTOMER SUCCESS IS NOT REACTIVE SUPPORT — IT IS A PROACTIVE SYSTEM THAT ENSURES CUSTOMERS ACHIEVE THEIR GOALS WITH YOUR PRODUCT, BECAUSE THEIR SUCCESS IS YOUR RETENTION.
Phase 1: Lifecycle Definition
Map the customer journey from purchase to advocacy.
Required Inputs
| Input | What to Ask | Default |
|---|---|---|
| Business model | "Subscription, project-based, retainer, or product?" | Subscription |
| Average customer lifetime | "How long does a typical customer stay?" | 12 months |
| Revenue per customer | "Average revenue per customer per year?" | No default |
| Churn rate | "What percentage of customers leave per year?" | Unknown |
| Current touchpoints | "When do you proactively reach out to customers today?" | Rarely / only when they contact us |
| Success definition | "What outcome means a customer is successful with your product?" | No default |
GATE: Confirm lifecycle context before designing the playbook.
Phase 2: Design Playbooks
Create stage-specific playbooks for the customer lifecycle.
Lifecycle Stages
## Customer Lifecycle Map
| Stage | Duration | Goal | Key Metric |
|-------|----------|------|-----------|
| Onboarding | Days 1-30 | First value realization | Time to first win |
| Adoption | Days 30-90 | Regular usage established | Feature adoption rate |
| Growth | Months 3-9 | Expanded usage and value | Expansion revenue |
| Renewal | Month 9-12 | Retention and commitment | Renewal rate |
| Advocacy | Ongoing | Referrals and testimonials | Referral count, NPS |
Stage Playbooks
Onboarding Playbook:
## Onboarding (Days 1-30)
**Touchpoints:**
- Day 1: Welcome email + first action prompt
- Day 3: Check-in — did they complete first action?
- Day 7: Quick call or video to confirm progress
- Day 14: Milestone check — are they using key features?
- Day 30: Onboarding review — health score baseline
**Success signals:** Completed setup, used core feature 3+ times, asked questions
**Risk signals:** No login after Day 3, no response to check-ins, support ticket filed
Adoption Playbook:
## Adoption (Days 30-90)
**Touchpoints:**
- Monthly check-in email with usage tips
- Day 45: Share a relevant case study or best practice
- Day 60: Proactive value review ("Here is what you have achieved so far")
- Day 90: Quarterly business review (formal or informal)
**Success signals:** Regular usage, exploring advanced features, positive feedback
**Risk signals:** Declining usage, no response to outreach, complaints about value
Growth Playbook:
## Growth (Months 3-9)
**Touchpoints:**
- Monthly value-add email (tips, features, industry insights)
- Quarterly business review
- Feature announcements relevant to their use case
- Expansion conversation when usage signals readiness
**Expansion triggers:**
- Customer hits usage limits
- Customer asks about additional features
- Customer's team or business is growing
- Customer achieves original goal and needs new ones
Renewal Playbook:
## Renewal (Month 9-12)
**Touchpoints:**
- Month 9: Pre-renewal health check and value summary
- Month 10: Renewal conversation with ROI data
- Month 11: Formal renewal proposal
- Month 12: Renewal confirmation or save conversation
**Renewal preparation:**
1. Compile value delivered (metrics, outcomes, usage data)
2. Identify any unresolved issues and fix them before renewal
3. Prepare expansion offer if appropriate
4. Have a save playbook ready if they hesitate
GATE: Present playbooks for review and customization.
Phase 3: Touchpoint Content
Write the key messages and templates.
Quarterly Business Review Template
## Quarterly Business Review: [Customer Name]
**Period:** [Quarter]
**Prepared by:** [Your name]
### Value Delivered
- [Metric 1: What they achieved using your product]
- [Metric 2: Time saved, revenue generated, problems solved]
- [Metric 3: Progress toward their stated goal]
### Usage Highlights
- [Feature/service usage data]
- [Adoption milestones reached]
### Recommendations
1. [Suggestion to deepen usage]
2. [Feature they have not tried yet]
3. [Best practice from similar customers]
### Next Quarter Goals
- [Goal aligned with their business objectives]
Save Conversation Framework
When a customer signals they may leave:
- Listen first — understand the real reason (do not sell)
- Acknowledge — validate their concern
- Address — present a specific solution to their issue
- Offer — if appropriate, provide a concession (discount, pause, service credit)
- Follow up — regardless of outcome, check in within 1 week
Phase 4: Measure
Track the effectiveness of the customer success program.
Success Metrics
## Customer Success Dashboard
| Metric | Target | Current |
|--------|--------|---------|
| Gross retention rate | 90%+ | — |
| Net revenue retention | 100%+ | — |
| Time to first value | Under [X] days | — |
| Quarterly business review completion | 80%+ | — |
| NPS score | 50+ | — |
| Expansion rate | [X]% of customers | — |
Monthly Review
- Which customers moved between lifecycle stages?
- Are touchpoints happening on schedule?
- Which playbook actions are driving the best outcomes?
- Are there new risk signals to add to the playbooks?
Anti-Patterns
- Reactive only — waiting for customers to contact you means you have already lost proactive influence.
- Same treatment for all customers — a new customer and a 2-year customer need different touchpoints. Stage matters.
- Touchpoints without value — "Just checking in" emails with no content get ignored. Every touchpoint must deliver value.
- Ignoring expansion signals — customers who hit usage limits and ask about features are buying signals. Do not miss them.
- No renewal preparation — starting the renewal conversation 30 days out is too late. Start at 90 days.
Recovery
- User has no customer data: Start with a simple spreadsheet: customer name, start date, last contact, health status (green/yellow/red). Build from there.
- User has too many customers to manage individually: Automate low-touch stages (onboarding emails, usage tips). Reserve manual effort for at-risk and expansion-ready accounts.
- Churn rate is high and unknown cause: Start with exit interviews for the next 5 churned customers. The patterns will emerge quickly.
- User is the only person doing customer success: Focus on the highest-value customers first. Automate or templatize everything possible.
- Customers do not respond to check-ins: Change the channel, the timing, or the content. A "Here is what you achieved" email gets more response than "Just checking in."