ORBWEVA Retention & Lifecycle Skill
Keep the customers you worked so hard to acquire. Lifecycle email sequences, satisfaction surveys, and retention strategies.
Commands
| Command | What it does |
|---|---|
/retain:emails |
Lifecycle email sequences (onboarding, engagement, win-back) |
/retain:nps |
NPS/CSAT survey design and analysis |
/retain:cohort |
Cohort analysis framework and interpretation |
/retain:playbook |
Full retention playbook with prioritized actions |
/retain:help |
Command reference |
Stage 1: Lifecycle Emails (/retain:emails)
Goal: Design email sequences for every stage of the customer lifecycle.
Onboarding Sequence (Days 0-14)
ONBOARDING EMAILS
==================
Goal: Get user to aha moment as fast as possible.
Aha moment: [define — e.g., "completed first project", "invited a teammate"]
DAY 0 — Welcome (immediate)
Subject: "Welcome to [Product] — here's your first step"
Content:
- What they can do RIGHT NOW (one specific action)
- Link to that action (not to docs, not to a tour — the action itself)
- Set expectation: "Over the next week, I'll send you 3 tips to get the most out of [Product]"
CTA: [Single action that leads to aha moment]
DAY 1 — Quick win
Subject: "[First name], try this in 2 minutes"
Content:
- One specific feature that delivers immediate value
- Screenshot or GIF showing the result
- Social proof: "[X users] did this in their first day"
CTA: [Try this feature]
DAY 3 — Core value
Subject: "The one thing power users do differently"
Content:
- The #1 behavior that correlates with retention
- How to do it (step by step)
- Before/after comparison
CTA: [Do the thing]
DAY 7 — Check-in
Subject: "How's it going with [Product]?"
Content:
- IF activated: "You've done [X] — here's what's next"
- IF not activated: "I noticed you haven't tried [aha action] yet. Here's why it matters."
- Personal tone (from founder, not "the team")
CTA: [Next step or reply to this email]
DAY 14 — Expand or recover
Subject (activated): "3 things you might not know about [Product]"
Subject (not activated): "Can I help?"
Content:
- Activated: Advanced features, integrations, invite teammates
- Not activated: Direct ask — "What's blocking you? Reply and I'll help."
CTA: [Expand usage or reply for help]
Engagement Sequence (ongoing)
ENGAGEMENT EMAILS
==================
Goal: Keep active users engaged and expanding.
Trigger: Usage-based, not time-based.
MILESTONE EMAIL
Trigger: User hits a usage milestone
Subject: "You just hit [milestone] — here's what that means"
Content: Celebrate + show next level + social comparison
USAGE DROP EMAIL
Trigger: Activity drops >50% from average for 2+ weeks
Subject: "We miss you at [Product]"
Content: NOT guilt. Show what they're missing (new features, team activity).
CTA: One-click return to their workspace
FEATURE ANNOUNCEMENT
Trigger: Ship something relevant to their usage pattern
Subject: "New: [Feature] — built for users like you"
Content: What it does + why it matters to THEM (based on usage)
CTA: Try it now
EXPANSION TRIGGER
Trigger: Approaching plan limit or team size threshold
Subject: "[First name], your team is growing"
Content: Show usage approaching limit + what the next tier unlocks
Tone: Helpful, not salesy
Win-Back Sequence (post-churn)
WIN-BACK EMAILS
=================
Goal: Re-engage churned users with new value.
DAY 30 (after churn)
Subject: "What's changed since you left"
Content:
- 2-3 specific improvements since they churned
- Acknowledge their reason for leaving (if captured)
- Special offer: [discount / free month / extended trial]
CTA: Come back and try [specific new thing]
DAY 90 (after churn)
Subject: "[Product] update — thought of you"
Content:
- Major feature announcement or milestone
- Customer success story relevant to their use case
CTA: See what's new
DAY 180 (after churn) — final attempt
Subject: "Last one from us"
Content:
- Respect their decision
- Leave the door open
- Unsubscribe option prominent
CTA: If you ever want to come back, [link]
Email Anti-Patterns
EMAIL MISTAKES
===============
[ ] Sending from "noreply@" — kills replies and trust
[ ] Daily emails in week 1 — overwhelming, causes unsubscribe
[ ] Feature lists instead of outcomes
[ ] Same email to activated and non-activated users
[ ] No personalization beyond first name
[ ] "Just checking in" with no value
[ ] Marketing emails to users who haven't activated yet
Output
Deliver: Complete email sequence for requested lifecycle stage + subject lines + trigger conditions + anti-pattern check.
Stage 2: NPS/CSAT Surveys (/retain:nps)
Goal: Measure satisfaction and identify at-risk customers.
NPS Survey
NPS (NET PROMOTER SCORE)
==========================
THE QUESTION:
"On a scale of 0-10, how likely are you to recommend [Product]
to a friend or colleague?"
Follow-up (required): "What's the primary reason for your score?"
SCORING:
9-10: Promoters (loyal, will refer)
7-8: Passives (satisfied but not enthusiastic)
0-6: Detractors (at risk, may churn or badmouth)
NPS = %Promoters - %Detractors (range: -100 to +100)
BENCHMARKS:
>50: Excellent (world-class)
30-50: Great
0-30: Good (room to improve)
<0: Concerning (more detractors than promoters)
WHEN TO SEND:
- After [X days/weeks] of active use (not immediately)
- Quarterly for ongoing measurement
- NOT after a support interaction (biased)
- NOT during onboarding (too early)
SEGMENTATION:
Always segment NPS by:
[ ] Plan tier (free vs paid)
[ ] Usage level (power user vs casual)
[ ] Tenure (new vs long-term)
[ ] Industry / role (if B2B)
The overall NPS is less useful than the segment analysis.
CSAT Survey
CSAT (CUSTOMER SATISFACTION SCORE)
====================================
THE QUESTION:
"How satisfied are you with [specific interaction/feature]?"
Scale: Very satisfied / Satisfied / Neutral / Dissatisfied / Very dissatisfied
CSAT = (Satisfied + Very Satisfied) / Total responses × 100
WHEN TO USE CSAT vs NPS:
NPS: Overall relationship health (quarterly)
CSAT: Specific touchpoint quality (after support, after feature use)
BEST PRACTICES:
[ ] Ask about specific interactions, not the product generally
[ ] Send within 24 hours of the interaction
[ ] Keep to 1-2 questions max
[ ] Always include open-text follow-up
[ ] Act on feedback visibly ("You asked, we built")
Output
Deliver: Survey design + sending triggers + scoring setup + segmentation plan + action framework for each score band.
Stage 3: Cohort Analysis (/retain:cohort)
Goal: Understand retention trends over time by grouping users into cohorts.
Cohort Table
COHORT RETENTION TABLE
========================
Cohort | M0 | M1 | M2 | M3 | M4 | M5 | M6
───────────┼───────┼───────┼───────┼───────┼───────┼───────┼──────
Jan (n=__) | 100% | ___% | ___% | ___% | ___% | ___% | ___%
Feb (n=__) | 100% | ___% | ___% | ___% | ___% | ___% |
Mar (n=__) | 100% | ___% | ___% | ___% | ___% | |
Apr (n=__) | 100% | ___% | ___% | ___% | | |
May (n=__) | 100% | ___% | ___% | | | |
Jun (n=__) | 100% | ___% | | | | |
WHAT TO LOOK FOR:
✓ Newer cohorts retain better than older ones → product improving
✓ Curves flatten after Month X → retained core exists
✗ Newer cohorts retain worse → product or market degrading
✗ No flattening → no retained core (PMF issue)
✗ Big drop at Month 1 → onboarding problem
Interpretation Guide
COMMON COHORT PATTERNS
========================
Pattern: "The Cliff"
Shape: Sharp drop in M1, then gradual decline
Meaning: Onboarding failure — users don't reach aha moment
Fix: Improve first-run experience, reduce time-to-value
Pattern: "The Plateau"
Shape: Moderate drop, then flattens at X%
Meaning: You have a retained core. Those users have PMF.
Fix: Get MORE users to look like the retained segment.
Pattern: "The Smile"
Shape: Drop, then curve back up
Meaning: Re-engagement is working (emails, notifications, new features)
Fix: Double down on re-engagement. Investigate what brings them back.
Pattern: "The Slide"
Shape: Continuous decline, never flattens
Meaning: No PMF. Users try it and leave permanently.
Fix: Go back to /discovery:interview. Something fundamental is wrong.
Output
Deliver: Cohort table + pattern identification + root cause analysis + specific actions.
Stage 4: Retention Playbook (/retain:playbook)
Goal: Prioritized retention strategy customized to the product.
Retention Audit
RETENTION AUDIT
================
Current metrics:
Monthly churn rate: ___%
NPS score: ___
Activation rate: ___%
Time to aha moment: ___
DAU/MAU ratio: ___
HEALTH CHECK:
[ ] Onboarding emails set up and personalized
[ ] Usage-drop detection and alert system
[ ] NPS/CSAT survey running quarterly
[ ] Cohort analysis reviewed monthly
[ ] Churn reasons categorized and tracked
[ ] Win-back sequence active
[ ] Expansion triggers identified
Missing items: ___/7 — prioritize in this order.
Retention Priority Stack
RETENTION PRIORITIES (fix in this order)
==========================================
1. ACTIVATION (if activation rate < 40%)
→ Users who don't activate WILL churn. Fix this first.
→ Actions: /retain:emails (onboarding sequence)
2. INVOLUNTARY CHURN (if failed payments > 2% of churn)
→ Easiest win. Set up dunning emails and card retry.
→ Actions: Payment retry logic + dunning sequence
3. EARLY CHURN (if M1 drop > 40%)
→ Onboarding isn't working. Users don't see value fast enough.
→ Actions: Reduce time-to-value, improve first-run experience
4. MID-TERM CHURN (if M3-6 retention declining)
→ Users saw value but it faded. Feature depth or habit issue.
→ Actions: Engagement emails, feature discovery, usage milestones
5. EXPANSION (if NRR < 100%)
→ Existing users aren't growing. Upsell opportunities missing.
→ Actions: Usage-based upgrade triggers, team invite flows
Output
Deliver: Retention audit + prioritized action plan + specific email/survey/process recommendations.
Principles
- Retention is the foundation. Acquiring users into a leaky bucket is expensive waste.
- Activate before you engage. No amount of lifecycle emails fixes a broken onboarding.
- Segment everything. Overall retention hides segment-level truths.
- Ask, then act visibly. Surveys without follow-through erode trust.
- Win-back is cheaper than acquisition. Churned users already know your product.