retention-optimization-expert
Mission : Reduce churn and improve retention through cohort analysis, at-risk user identification, win-back campaigns, product improvements, and customer success strategies. Turn one-time users into lifelong customers.
STEP 0: Pre-Generation Verification
Before generating the HTML output, verify all required data is collected:
Header & Score Banner
Executive Summary
Cohort Analysis
Segment Retention
At-Risk Identification
Health Score
Win-Back Campaign
Churn Reasons
Retention Loops
Customer Success
Charts
Success Metrics
Roadmap
STEP 1: Detect Previous Context
Ideal Context (All Present):
metrics-dashboard-designer → Retention metrics, cohort data, churn rates
customer-persona-builder → User segments, behavioral patterns
product-positioning-expert → Value delivered, success indicators
onboarding-flow-optimizer → Activation rates, early retention data
customer-feedback-framework → Churn reasons, exit surveys, NPS
Partial Context (Some Present):
metrics-dashboard-designer → Retention metrics available
customer-persona-builder → User segmentation available
onboarding-flow-optimizer → Onboarding data available
No Context:
None of the above skills were run
STEP 2: Context-Adaptive Introduction
If Ideal Context:
I found outputs from metrics-dashboard-designer , customer-persona-builder , product-positioning-expert , onboarding-flow-optimizer , and customer-feedback-framework .
I can reuse:
Retention metrics (D1/D7/D30 retention: [X%], churn rate: [Y%], cohort curves)
User segments ([Segment A], [Segment B], [Segment C])
Value delivered (core features that drive retention)
Activation rates ([X%] of users activated within 7 days)
Churn reasons (top 3: [Reason 1], [Reason 2], [Reason 3])
Proceed with this data? [Yes/Start Fresh]
If Partial Context:
I found outputs from some upstream skills: [list which ones].
I can reuse: [list specific data available]
Proceed with this data, or start fresh?
If No Context:
No previous context detected.
I'll guide you through optimizing retention from the ground up.
STEP 3: Questions (One at a Time, Sequential)
Current Retention Baseline
Question RB1: What is your current retention performance?
Retention Metrics :
Day 1 Retention : [X%] (users who return the next day)
Day 7 Retention : [X%] (users who return within a week)
Day 30 Retention : [X%] (users who return within a month)
6-Month Retention : [X%] (users still active after 6 months)
Churn Metrics :
User Churn Rate : [X% per month]
Revenue Churn Rate : [X% MRR per month]
Logo Churn Rate : [X% customers per month] (B2B companies)
Industry Benchmarks (for context):
Consumer Apps : D30 retention 20-30%
SaaS Products : D30 retention 30-50%, monthly churn <5%
Social Networks : D30 retention 40-60%
E-commerce : 6-month retention 20-40%
Your Performance vs. Benchmark :
Current D30 Retention: [X%]
Benchmark D30 Retention: [Y%]
Gap: [Z percentage points]
Question RB2: What does your retention curve look like?
Retention Curve Analysis :
Plot retention over time (Day 0, Day 1, Day 7, Day 14, Day 30, Day 60, Day 90...):
100% ┤
│●
75% ┤ ●
│ ●
50% ┤ ●_______________
│ ●●●●●● [plateau = retained users]
25% ┤
│
0% └───────────────────────────────────────────
0 7 14 30 60 90 120 [days]
Retention Curve Type :
☐ Steep drop, then plateau (good — you retain a core user base)
☐ Continuous decline (bad — users keep leaving, no plateau)
☐ Gradual decline, small plateau (okay — some retention, needs improvement)
Your Curve : [Describe shape, when plateau occurs, plateau level]
Critical Retention Milestones :
Day 1 → Day 7 : [X% retention — early drop-off period]
Day 7 → Day 30 : [X% retention — product-market fit test]
Day 30 → Day 90 : [X% retention — habit formation period]
Cohort Analysis
Question CA1: How does retention vary by cohort?
Cohort Definition : Group users by signup month (January cohort, February cohort, etc.)
Cohort Retention Table :
Cohort
M0 (Signup)
M1
M2
M3
M6
M12
Jan 2024
100%
42%
35%
30%
25%
20%
Feb 2024
100%
45%
38%
32%
27%
—
Mar 2024
100%
48%
40%
34%
—
—
Apr 2024
100%
50%
42%
—
—
—
Cohort Insights :
Are newer cohorts retaining better? [Yes/No — if yes, what changed?]
Which cohort has the highest retention? [Month + retention %]
Which cohort has the lowest retention? [Month + retention %]
Cohort Improvement Trend :
☐ Improving (newer cohorts retain better — product/onboarding improvements working)
☐ Flat (cohorts retain similarly — no major changes)
☐ Declining (newer cohorts retain worse — product quality or ICP drift)
Question CA2: How does retention vary by user segment?
Segment Retention Comparison :
Segment
D30 Retention
Churn Rate
Why the difference?
[Segment A]
X%
Y%
[e.g., "Power users, use product daily"]
[Segment B]
X%
Y%
[e.g., "Casual users, weekly usage"]
[Segment C]
X%
Y%
[e.g., "Trial users, haven't upgraded"]
[By Acquisition Source]
—
—
—
Organic Search
X%
Y%
[Higher intent, better fit]
Paid Search
X%
Y%
[Lower intent, higher churn]
Referral
X%
Y%
[Best retention — referred by friends]
Social Media
X%
Y%
[Impulse signups, lower retention]
Best Retaining Segment : [Which segment?]
Worst Retaining Segment : [Which segment?]
Action :
Double down on acquiring users similar to best-retaining segment
Improve onboarding for worst-retaining segment or stop acquiring them
Churn Prediction & At-Risk Users
Question CP1: Can you identify at-risk users before they churn?
At-Risk User Definition (users showing declining engagement):
Leading Indicators of Churn (2-4 weeks before churn):
Declining Login Frequency : [e.g., "User logged in 10x last month, only 3x this month"]
Reduced Feature Usage : [e.g., "User stopped using core feature X"]
Lower Session Duration : [e.g., "Average session dropped from 8 min to 2 min"]
Support Tickets : [e.g., "User submitted 3+ bug reports"]
Payment Issues : [e.g., "Credit card declined, didn't update"]
No Activity in X Days : [e.g., "No login in 14+ days"]
Your At-Risk Criteria (choose 3-5):
[Indicator 1] — e.g., "No login in 14 days"
[Indicator 2] — e.g., "Session frequency dropped >50%"
[Indicator 3] — e.g., "Didn't use core feature in last 30 days"
At-Risk User Count :
Total Active Users: [X]
At-Risk Users (meeting 2+ criteria): [Y]
% At Risk: [Z%]
Question CP2: What is your plan to re-engage at-risk users?
Win-Back Campaign (multi-channel, escalating touchpoints):
Tier 1: Subtle Re-Engagement (Days 7-14 inactive)
Email 1 : "We miss you! Here's what's new" (feature updates, product improvements)
In-App Notification : "You haven't logged in recently. Come back for [incentive]"
Push Notification (if mobile app): "Your [X] is waiting for you"
Tier 2: Value Reminder (Days 15-21 inactive)
Email 2 : "Remember why you signed up? Here's how [Product] helps with [pain point]"
Case Study : "How [Customer Name] achieved [result] with [Product]"
Personal Outreach (for high-value users): CEO/CSM sends personal email
Tier 3: Incentive (Days 22-30 inactive)
Email 3 : "We'd love to have you back. Here's [discount/free month/bonus credits]"
Survey : "What would bring you back? We're listening" (with incentive for completing)
Tier 4: Last Chance (Days 30+ inactive)
Email 4 : "Last chance to keep your data. Account will be deactivated in 7 days"
Phone Call (for enterprise): CSM calls to understand churn reason and offer solutions
Win-Back Channels (choose 3-5):
☐ Email (sequence of 3-4 emails)
☐ In-app notifications
☐ Push notifications (mobile)
☐ SMS (high-value users only)
☐ Retargeting ads (Facebook, Google)
☐ Personal outreach (phone, LinkedIn)
Win-Back Success Metrics :
Open Rate : [Target: >25%]
Click Rate : [Target: >10%]
Reactivation Rate : [Target: >5% of inactive users return]
Churn Reasons & Exit Analysis
Question CR1: Why do users churn?
Exit Survey (trigger when user cancels or becomes inactive):
Question 1 : Why are you leaving?
☐ Too expensive
☐ Didn't see value / wasn't using it
☐ Missing features I need
☐ Found a better alternative
☐ Too complicated / hard to use
☐ Poor customer support
☐ Technical issues / bugs
☐ Other: [open text]
Question 2 : What would have kept you as a customer?
Question 3 : Would you consider returning in the future?
☐ Yes, if [condition]
☐ No
Churn Reason Breakdown (based on exit surveys + data analysis):
Churn Reason
% of Churned Users
Addressable?
Action Plan
Didn't see value / low usage
X%
✅ Yes
Improve onboarding, activation
Too expensive
X%
✅ Yes
Introduce lower-tier plan, annual discount
Missing features
X%
✅ Yes
Build top-requested features
Found better alternative
X%
⚠️ Maybe
Competitive analysis, differentiate
Too complicated
X%
✅ Yes
Simplify UI, improve help docs
Poor support
X%
✅ Yes
Hire more support, reduce response time
Technical issues
X%
✅ Yes
Fix bugs, improve performance
Company shut down / no longer needed
X%
❌ No
Unavoidable churn
Top 3 Addressable Churn Reasons :
[Reason 1] — [Action plan]
[Reason 2] — [Action plan]
[Reason 3] — [Action plan]
Question CR2: How can you reduce involuntary churn?
Involuntary Churn = Users who churn due to failed payments (not because they wanted to leave)
Payment Failure Reasons :
Expired credit card
Insufficient funds
Bank decline (fraud alert)
Card changed (lost/stolen)
Dunning Campaign (recover failed payments):
Failed Payment Day 0:
Email 1 : "Payment failed. Please update your payment method" (link to billing page)
In-app banner : "Action required: Update payment method"
Day 3:
Email 2 : "Reminder: Your payment failed. Update card to keep access"
Grace period : Keep product access for 7-14 days
Day 7:
Email 3 : "Final reminder: Update payment or service will be suspended in 3 days"
SMS (optional): "Your [Product] account will be suspended. Update payment now"
Day 10:
Suspend Service : Downgrade to free plan or suspend account
Email 4 : "Account suspended. Update payment to restore access"
Smart Dunning Tactics :
Retry Schedule : Retry failed payment 3 times (Day 0, Day 3, Day 7)
Alternative Payment Methods : Offer PayPal, bank transfer, crypto
Update Card Before Expiry : Email users 30 days before card expires
Involuntary Churn Rate :
Current: [X% of total churn]
Target: [<20% of total churn]
Retention Loops & Product Improvements
Question RL1: What retention loops can you build?
Retention Loop = A repeating cycle that brings users back to the product
Examples :
Content Drip Loop (e.g., Duolingo, Netflix)
New content released regularly (daily lessons, weekly episodes)
Push notification: "Your [new content] is ready"
User returns → consumes content → waits for next drop
Social Loop (e.g., LinkedIn, Facebook)
User posts content
Followers engage (likes, comments)
Push notification: "[Friend] commented on your post"
User returns → engages → posts again
Progress Loop (e.g., Strava, MyFitnessPal)
User logs progress (workout, meal, habit)
App shows streaks, achievements, leaderboards
User returns to maintain streak → logs progress → cycle continues
Collaboration Loop (e.g., Slack, Figma, Notion)
User invites team members
Team collaborates in product
Notifications: "[@mention] left a comment"
User returns → collaborates → cycle continues
Email Digest Loop (e.g., Substack, Reddit)
User subscribes to digest (daily, weekly)
Email: "Here's what you missed this week"
User clicks → returns to product → subscribes again
Your Retention Loop(s) (choose 1-3):
[Loop Type] : [How it works — trigger → action → return]
[Loop Type] : [How it works]
[Loop Type] : [How it works]
Implementation Plan :
Loop 1: [What needs to be built? Timeline?]
Loop 2: [What needs to be built? Timeline?]
Question RL2: What product improvements will reduce churn?
Churn-Reducing Product Changes (based on churn reasons and user feedback):
Churn Reason
Product Improvement
Priority
Timeline
"Didn't see value / low usage"
Improve onboarding, add activation checklist
High
4 weeks
"Missing feature X"
Build feature X (top-requested)
High
8 weeks
"Too complicated"
Simplify UI, add tooltips, create video tutorials
Medium
6 weeks
"Technical issues"
Fix top 5 bugs, improve performance
High
2 weeks
"Poor support"
Hire 2 support reps, reduce response time to <2 hours
Medium
4 weeks
Quick Wins (implement in next 30 days):
[Improvement 1] — e.g., "Add onboarding checklist (3 tasks to activation)"
[Improvement 2] — e.g., "Fix top 3 bugs causing user frustration"
[Improvement 3] — e.g., "Send weekly email digest to inactive users"
Long-Term Bets (implement in next 90 days):
[Improvement 1] — e.g., "Build top-requested feature (X)"
[Improvement 2] — e.g., "Redesign core workflow to reduce friction"
[Improvement 3] — e.g., "Add social features (commenting, sharing)"
Customer Success Strategy
Question CS1: What is your customer success strategy?
Customer Success Model (choose based on ARPU and scale):
ARPU
Model
CS Ratio
Touchpoints
<$100/mo
Tech-Touch (automated)
1 CSM : ∞ users
Email, in-app, chatbot, self-service resources
$100-$500/mo
Hybrid (light-touch)
1 CSM : 100-200
Quarterly check-ins, email, webinars, resources
$500-$2k/mo
High-Touch (proactive)
1 CSM : 50-100
Monthly QBRs, onboarding, ongoing support
>$2k/mo
White-Glove (dedicated)
1 CSM : 10-30
Dedicated CSM, weekly check-ins, custom success plan
Your Model : [Tech-Touch / Hybrid / High-Touch / White-Glove]
Customer Success Touchpoints :
Onboarding (Days 0-30):
Day 0 : Welcome email + onboarding checklist
Day 3 : Check-in email: "How's onboarding going? Need help?"
Day 7 : Onboarding call (high-touch) or webinar (light-touch)
Day 14 : Feature tutorial: "Here's how to use [power feature]"
Day 30 : Success check-in: "Did you achieve [goal]?"
Ongoing Success (Month 2+):
Monthly : Usage report: "Here's your activity this month"
Quarterly : QBR (Quarterly Business Review) — review goals, usage, ROI
Ad Hoc : Trigger-based outreach (e.g., usage drops, feature launch, renewal coming up)
Renewal/Expansion (30-60 days before renewal):
Renewal campaign : "Your contract renews in 60 days. Let's review value delivered"
Expansion conversation : "You're using X feature heavily. Have you considered Y feature?"
Customer Health Score (predict churn risk):
Factor
Weight
Healthy
At Risk
Churn Risk
Login Frequency
30%
10+ /mo
3-9 /mo
<3 /mo
Feature Usage (core features)
25%
80%+
40-79%
<40%
Support Tickets (open)
15%
0-1
2-3
4+
NPS Score
15%
9-10
7-8
0-6
Payment Status
15%
Current
Late
Failed
Health Score Calculation :
Green (80-100) : Healthy, potential for expansion
Yellow (50-79) : At risk, requires proactive outreach
Red (<50) : Churn risk, urgent intervention
Current Health Score Distribution :
Green: [X%] of customers
Yellow: [Y%] of customers
Red: [Z%] of customers
Question CS2: How will you scale customer success?
Scaling Customer Success (as you grow from 100 → 1,000 → 10,000 customers):
Phase 1: Manual (0-100 customers)
1 CSM handles all customers
Personal touch: emails, calls, QBRs
Learn what works, document best practices
Phase 2: Semi-Automated (100-1,000 customers)
Segment customers (high-value = high-touch, low-value = tech-touch)
Automate touchpoints (email sequences, in-app messages, webinars)
Hire 2-3 CSMs for high-value accounts
Phase 3: Fully Scaled (1,000+ customers)
CSM team by segment : Enterprise (white-glove), Mid-Market (high-touch), SMB (tech-touch)
Self-service resources : Help center, video tutorials, community forum
Proactive monitoring : Health score dashboard, automated alerts for at-risk accounts
Your Scaling Plan :
Current customer count: [X]
Current CSM count: [Y]
Next hire milestone: [When you reach Z customers, hire CSM #N]
Implementation Roadmap
Question IR1: What is your 90-day retention optimization plan?
Phase 1: Analyze (Weeks 1-3)
Goal : Understand why users churn and identify at-risk segments
Deliverable : Retention analysis report with top 3 churn drivers and at-risk user list
Phase 2: Intervene (Weeks 4-6)
Goal : Launch win-back campaigns and reduce involuntary churn
Deliverable : Win-back and dunning campaigns live, 20% of at-risk high-value users contacted
Phase 3: Improve Product (Weeks 7-12)
Goal : Build retention loops and fix top churn drivers
Deliverable : Retention loop live, top churn drivers addressed via product improvements
Phase 4: Monitor & Iterate (Ongoing)
Goal : Track retention metrics and continuously optimize
Weekly : Review at-risk user list, reach out to red-health-score users
Monthly : Review cohort retention, churn rate, win-back campaign performance
Quarterly : Deep dive into churn reasons, prioritize product improvements
Success Metrics (track over 90 days):
D30 Retention : [Baseline → Target — e.g., 35% → 45%]
Churn Rate : [Baseline → Target — e.g., 8% → 5%]
Win-Back Reactivation Rate : [Target: 5-10% of inactive users return]
Involuntary Churn : [Baseline → Target — e.g., 30% of churn → <20% of churn]
Health Score : [% of users in Green — e.g., 60% → 75%]
STEP 4: Generate Comprehensive Retention Optimization Strategy
You will now receive a comprehensive document covering :
Section 1: Executive Summary
Current retention performance (D1/D7/D30, churn rate)
Retention curve shape and critical drop-off points
Top 3 churn drivers and action plans
Section 2: Cohort Analysis Deep Dive
Cohort retention table (M0, M1, M3, M6, M12)
Cohort improvement trend (improving, flat, declining)
Segment retention comparison (by persona, acquisition source, plan tier)
Best-retaining and worst-retaining segments
Section 3: Churn Prediction & At-Risk Users
At-risk user criteria (3-5 leading indicators)
At-risk user count and % of user base
Customer health score model (5 factors, weighted)
Health score distribution (Green, Yellow, Red)
Section 4: Win-Back & Dunning Campaigns
Win-Back Campaign : 4-tier email sequence (Days 7, 14, 21, 30 inactive)
Dunning Campaign : Payment failure recovery (Day 0, 3, 7, 10)
Win-back channels (email, in-app, push, SMS, retargeting, personal outreach)
Success metrics (open rate, click rate, reactivation rate)
Section 5: Churn Reason Analysis
Exit survey questions (3 key questions)
Churn reason breakdown (% of churned users, addressable?, action plan)
Top 3 addressable churn reasons with action plans
Involuntary churn strategy (dunning, grace period, alternative payments)
Section 6: Retention Loops & Product Improvements
Retention Loops (1-3 loops: content drip, social, progress, collaboration, email digest)
Quick Wins (implement in 30 days: onboarding checklist, bug fixes, email digest)
Long-Term Bets (implement in 90 days: build top feature, redesign workflow, add social features)
Section 7: Customer Success Strategy
Customer success model (tech-touch, hybrid, high-touch, white-glove)
Touchpoints (onboarding Days 0-30, ongoing success, renewal/expansion)
Customer health score calculation (5 factors, Green/Yellow/Red)
Scaling plan (manual → semi-automated → fully scaled)
Section 8: Implementation Roadmap
Phase 1 (Weeks 1-3) : Cohort analysis, churn reason analysis, at-risk user identification
Phase 2 (Weeks 4-6) : Win-back campaign, dunning campaign, personal outreach
Phase 3 (Weeks 7-12) : Quick wins, retention loop, feature improvements
Phase 4 (Ongoing) : Monitor metrics, weekly/monthly/quarterly reviews
Section 9: Success Metrics
D30 Retention: [Baseline → Target]
Churn Rate: [Baseline → Target]
Win-Back Reactivation Rate: [Target: 5-10%]
Involuntary Churn: [<20% of total churn]
Health Score: [75%+ of users in Green]
Section 10: Next Steps
Launch win-back campaign this week
Schedule monthly retention review meetings
Integrate with customer-feedback-framework (use exit surveys to gather churn reasons)
Integrate with onboarding-flow-optimizer (improve early retention via better activation)
STEP 5: Quality Review & Iteration
After generating the strategy, I will ask:
Quality Check :
Is the retention baseline and target realistic? (D30 retention 35% → 45% in 90 days is achievable)
Are churn reasons based on real data (exit surveys, user interviews)?
Are at-risk criteria measurable and actionable?
Is the win-back campaign multi-channel and escalating?
Are retention loops feasible to build in the given timeline?
Is the customer success model appropriate for your ARPU and scale?
Iterate? [Yes — refine X / No — finalize]
STEP 6: Save & Next Steps
Once finalized, I will:
Save the retention optimization strategy to your project folder
Suggest running onboarding-flow-optimizer next (to improve early retention)
Remind you to launch the win-back campaign this week
8 Critical Guidelines for This Skill
Retention > Acquisition : It's 5-7x cheaper to retain a customer than acquire a new one. Prioritize retention over growth.
Cohort analysis is essential : Don't just track overall retention. Track by cohort (signup month) and segment (persona, acquisition source, plan tier).
At-risk users can be saved : Identify users showing declining engagement 2-4 weeks before they churn, and intervene proactively.
Involuntary churn is addressable : 20-40% of churn is due to failed payments. Implement dunning campaigns to recover revenue.
Exit surveys are mandatory : You can't fix churn if you don't know why users leave. Trigger exit surveys on cancellation.
Retention loops > one-time campaigns : Build repeating cycles (content drip, social, progress) that bring users back automatically.
Health scores predict churn : Track 5 factors (login frequency, feature usage, support tickets, NPS, payment status) to calculate customer health.
Customer success scales with ARPU : Low ARPU = tech-touch (automated). High ARPU = high-touch (dedicated CSM).
Quality Checklist (Before Finalizing)
Retention baseline and targets are clearly defined (D1/D7/D30, churn rate)
Cohort analysis shows retention by signup month and user segment
At-risk user criteria are measurable (3-5 leading indicators)
Win-back campaign is multi-channel with 4 touchpoints (Days 7, 14, 21, 30)
Dunning campaign is implemented to reduce involuntary churn
Top 3 churn reasons are identified with action plans
1-3 retention loops are defined (content drip, social, progress, collaboration, email digest)
Customer success model matches your ARPU and scale
Implementation roadmap is realistic (Weeks 1-3: Analyze, Weeks 4-6: Intervene, Weeks 7-12: Improve)
Success metrics are tracked (D30 retention, churn rate, win-back reactivation, involuntary churn, health score)
Integration with Other Skills
Upstream Skills (reuse data from):
metrics-dashboard-designer → Retention metrics, cohort data, churn rates, health scores
customer-persona-builder → User segments for cohort analysis
product-positioning-expert → Value delivered, success indicators
onboarding-flow-optimizer → Activation rates, early retention data
customer-feedback-framework → Churn reasons, exit surveys, NPS, CSAT
email-marketing-architect → Win-back email sequences, drip campaigns
growth-hacking-playbook → Retention loops (AARRR framework)
Downstream Skills (use this data in):
customer-feedback-framework → Gather feedback from churned users and at-risk users
onboarding-flow-optimizer → Improve early retention (D1-D7) via better onboarding and activation
product roadmap → Prioritize features that reduce churn (top-requested features, bug fixes)
investor-pitch-deck-builder → Use improved retention metrics in traction slides
financial-model-architect → Use lower churn rate to project revenue and LTV
HTML Output Verification
After generating the HTML report, verify all elements render correctly:
Visual Verification Checklist
Data Quality Verification
Template Location
Skeleton template: html-templates/retention-optimization-expert.html
Test output: skills/retention-metrics/retention-optimization-expert/test-template-output.html
End of Skill
1 --- 2 name: retention-optimization-expert 3 description: Reduce churn and improve retention through cohort analysis, at-risk user identification, win-back campaigns, and customer success strategies. Generate comprehensive HTML reports with retention curves, health scores, churn analysis, and 90-day implementation roadmaps. 4 --- 5
6 # retention-optimization-expert
7
8 **Mission**: Reduce churn and improve retention through cohort analysis, at-risk user identification, win-back campaigns, product improvements, and customer success strategies. Turn one-time users into lifelong customers.
9
10 ---
11
12 ## STEP 0: Pre-Generation Verification
13
14 Before generating the HTML output, verify all required data is collected:
15
16 ### Header & Score Banner
17 - [ ] `{{BUSINESS_NAME}}` - Company/product name
18 - [ ] `{{DATE}}` - Report generation date
19 - [ ] `{{D30_RETENTION}}` - 30-day retention rate (e.g., "38%")
20 - [ ] `{{D7_RETENTION}}` - 7-day retention rate (e.g., "52%")
21 - [ ] `{{CHURN_RATE}}` - Monthly churn rate (e.g., "6.2%")
22 - [ ] `{{AT_RISK_PERCENT}}` - Percentage of at-risk users (e.g., "18%")
23 - [ ] `{{HEALTH_GREEN}}` - Percentage of healthy users (e.g., "62%")
24 - [ ] `{{CURVE_TYPE}}` - Short curve type (e.g., "Steep Drop + Plateau")
25
26 ### Executive Summary
27 - [ ] `{{EXECUTIVE_SUMMARY}}` - 2-3 paragraphs with retention overview, key interventions
28 - [ ] `{{CURVE_TYPE_FULL}}` - Full curve description (e.g., "Steep Drop, Then Plateau (Good)")
29 - [ ] `{{CURVE_DESCRIPTION}}` - Explanation of what the curve means for the business
30
31 ### Cohort Analysis
32 - [ ] `{{COHORT_ROWS}}` - 4+ cohort rows with M0-M6 retention percentages
33 - Each row: cohort name, M0 (100%), M1, M2, M3, M6 with color classes
34
35 ### Segment Retention
36 - [ ] `{{SEGMENT_CARDS}}` - 3-4 user segments
37 - Each card: segment name, D30 retention, churn rate
38
39 ### At-Risk Identification
40 - [ ] `{{RISK_INDICATORS}}` - 4-5 at-risk criteria
41 - Each indicator: icon, title, description of criteria
42
43 ### Health Score
44 - [ ] `{{HEALTH_GREEN}}` - Healthy percentage (80-100 score)
45 - [ ] `{{HEALTH_YELLOW}}` - At-risk percentage (50-79 score)
46 - [ ] `{{HEALTH_RED}}` - Churn risk percentage (<50 score)
47 - [ ] `{{HEALTH_FACTORS}}` - 5 health score factors with weights
48
49 ### Win-Back Campaign
50 - [ ] `{{WINBACK_TIERS}}` - 4 escalating tiers
51 - Each tier: name, day range, 2-4 actions
52
53 ### Churn Reasons
54 - [ ] `{{CHURN_ROWS}}` - 5-6 churn reasons
55 - Each row: reason, percentage, addressable status, action plan
56
57 ### Retention Loops
58 - [ ] `{{LOOP_CARDS}}` - 2-3 retention loops
59 - Each card: loop type, description, 3-4 cycle steps
60
61 ### Customer Success
62 - [ ] `{{CS_MODEL_NAME}}` - CS model name (e.g., "Hybrid Model")
63 - [ ] `{{CS_MODEL_RATIO}}` - CSM to account ratios
64 - [ ] `{{TOUCHPOINT_PHASES}}` - 3 phases (Onboarding, Ongoing, Renewal)
65 - Each phase: name, 4-5 touchpoints
66
67 ### Charts
68 - [ ] `{{RETENTION_LABELS}}` - JSON array of time periods (D0, D1, D7, etc.)
69 - [ ] `{{RETENTION_DATA}}` - JSON array of retention percentages
70 - [ ] `{{COHORT_LABELS}}` - JSON array of cohort names
71 - [ ] `{{COHORT_DATA}}` - JSON array of M3 retention rates
72 - [ ] `{{CHURN_LABELS}}` - JSON array of churn reason labels
73 - [ ] `{{CHURN_DATA}}` - JSON array of churn percentages
74 - [ ] `{{HEALTH_DATA}}` - JSON array [healthy%, at-risk%, churn-risk%]
75
76 ### Success Metrics
77 - [ ] `{{METRIC_CARDS}}` - 5 key metrics with baseline and target values
78
79 ### Roadmap
80 - [ ] `{{ROADMAP_PHASES}}` - 4 phases (Analyze, Intervene, Improve, Monitor)
81 - Each phase: name, timing, goal, 4-5 tasks
82
83 ---
84
85 ## STEP 1: Detect Previous Context
86
87 ### Ideal Context (All Present):
88 - **metrics-dashboard-designer** → Retention metrics, cohort data, churn rates
89 - **customer-persona-builder** → User segments, behavioral patterns
90 - **product-positioning-expert** → Value delivered, success indicators
91 - **onboarding-flow-optimizer** → Activation rates, early retention data
92 - **customer-feedback-framework** → Churn reasons, exit surveys, NPS
93
94 ### Partial Context (Some Present):
95 - **metrics-dashboard-designer** → Retention metrics available
96 - **customer-persona-builder** → User segmentation available
97 - **onboarding-flow-optimizer** → Onboarding data available
98
99 ### No Context:
100 - None of the above skills were run
101
102 ---
103
104 ## STEP 2: Context-Adaptive Introduction
105
106 ### If Ideal Context:
107 > I found outputs from **metrics-dashboard-designer**, **customer-persona-builder**, **product-positioning-expert**, **onboarding-flow-optimizer**, and **customer-feedback-framework**.
108 >
109 > I can reuse:
110 > - **Retention metrics** (D1/D7/D30 retention: [X%], churn rate: [Y%], cohort curves)
111 > - **User segments** ([Segment A], [Segment B], [Segment C])
112 > - **Value delivered** (core features that drive retention)
113 > - **Activation rates** ([X%] of users activated within 7 days)
114 > - **Churn reasons** (top 3: [Reason 1], [Reason 2], [Reason 3])
115 >
116 > **Proceed with this data?** [Yes/Start Fresh]
117
118 ### If Partial Context:
119 > I found outputs from some upstream skills: [list which ones].
120 >
121 > I can reuse: [list specific data available]
122 >
123 > **Proceed with this data, or start fresh?**
124
125 ### If No Context:
126 > No previous context detected.
127 >
128 > I'll guide you through optimizing retention from the ground up.
129
130 ---
131
132 ## STEP 3: Questions (One at a Time, Sequential)
133
134 ### Current Retention Baseline
135
136 **Question RB1: What is your current retention performance?**
137
138 **Retention Metrics**:
139 - **Day 1 Retention**: [X%] (users who return the next day)
140 - **Day 7 Retention**: [X%] (users who return within a week)
141 - **Day 30 Retention**: [X%] (users who return within a month)
142 - **6-Month Retention**: [X%] (users still active after 6 months)
143
144 **Churn Metrics**:
145 - **User Churn Rate**: [X% per month]
146 - **Revenue Churn Rate**: [X% MRR per month]
147 - **Logo Churn Rate**: [X% customers per month] (B2B companies)
148
149 **Industry Benchmarks** (for context):
150 - **Consumer Apps**: D30 retention 20-30%
151 - **SaaS Products**: D30 retention 30-50%, monthly churn <5%
152 - **Social Networks**: D30 retention 40-60%
153 - **E-commerce**: 6-month retention 20-40%
154
155 **Your Performance vs. Benchmark**:
156 - Current D30 Retention: [X%]
157 - Benchmark D30 Retention: [Y%]
158 - Gap: [Z percentage points]
159
160 ---
161
162 **Question RB2: What does your retention curve look like?**
163
164 **Retention Curve Analysis**:
165
166 Plot retention over time (Day 0, Day 1, Day 7, Day 14, Day 30, Day 60, Day 90...):
167
168 ```
169 100% ┤
170 │●
171 75% ┤ ●
172 │ ●
173 50% ┤ ●_______________
174 │ ●●●●●● [plateau = retained users]
175 25% ┤
176 │
177 0% └───────────────────────────────────────────
178 0 7 14 30 60 90 120 [days]
179 ```
180
181 **Retention Curve Type**:
182 - ☐ **Steep drop, then plateau** (good — you retain a core user base)
183 - ☐ **Continuous decline** (bad — users keep leaving, no plateau)
184 - ☐ **Gradual decline, small plateau** (okay — some retention, needs improvement)
185
186 **Your Curve**: [Describe shape, when plateau occurs, plateau level]
187
188 **Critical Retention Milestones**:
189 - **Day 1 → Day 7**: [X% retention — early drop-off period]
190 - **Day 7 → Day 30**: [X% retention — product-market fit test]
191 - **Day 30 → Day 90**: [X% retention — habit formation period]
192
193 ---
194
195 ### Cohort Analysis
196
197 **Question CA1: How does retention vary by cohort?**
198
199 **Cohort Definition**: Group users by signup month (January cohort, February cohort, etc.)
200
201 **Cohort Retention Table**:
202
203 | Cohort | M0 (Signup) | M1 | M2 | M3 | M6 | M12 |
204 |-----------|-------------|------|------|------|------|------|
205 | Jan 2024 | 100% | 42% | 35% | 30% | 25% | 20% |
206 | Feb 2024 | 100% | 45% | 38% | 32% | 27% | — |
207 | Mar 2024 | 100% | 48% | 40% | 34% | — | — |
208 | Apr 2024 | 100% | 50% | 42% | — | — | — |
209
210 **Cohort Insights**:
211 - Are newer cohorts retaining better? [Yes/No — if yes, what changed?]
212 - Which cohort has the highest retention? [Month + retention %]
213 - Which cohort has the lowest retention? [Month + retention %]
214
215 **Cohort Improvement Trend**:
216 - ☐ **Improving** (newer cohorts retain better — product/onboarding improvements working)
217 - ☐ **Flat** (cohorts retain similarly — no major changes)
218 - ☐ **Declining** (newer cohorts retain worse — product quality or ICP drift)
219
220 ---
221
222 **Question CA2: How does retention vary by user segment?**
223
224 **Segment Retention Comparison**:
225
226 | Segment | D30 Retention | Churn Rate | Why the difference? |
227 |------------------------|---------------|------------|----------------------------------------------|
228 | [Segment A] | X% | Y% | [e.g., "Power users, use product daily"] |
229 | [Segment B] | X% | Y% | [e.g., "Casual users, weekly usage"] |
230 | [Segment C] | X% | Y% | [e.g., "Trial users, haven't upgraded"] |
231 | [By Acquisition Source]| — | — | — |
232 | Organic Search | X% | Y% | [Higher intent, better fit] |
233 | Paid Search | X% | Y% | [Lower intent, higher churn] |
234 | Referral | X% | Y% | [Best retention — referred by friends] |
235 | Social Media | X% | Y% | [Impulse signups, lower retention] |
236
237 **Best Retaining Segment**: [Which segment?]
238 **Worst Retaining Segment**: [Which segment?]
239
240 **Action**:
241 - Double down on acquiring users similar to best-retaining segment
242 - Improve onboarding for worst-retaining segment or stop acquiring them
243
244 ---
245
246 ### Churn Prediction & At-Risk Users
247
248 **Question CP1: Can you identify at-risk users before they churn?**
249
250 **At-Risk User Definition** (users showing declining engagement):
251
252 **Leading Indicators of Churn** (2-4 weeks before churn):
253 1. **Declining Login Frequency**: [e.g., "User logged in 10x last month, only 3x this month"]
254 2. **Reduced Feature Usage**: [e.g., "User stopped using core feature X"]
255 3. **Lower Session Duration**: [e.g., "Average session dropped from 8 min to 2 min"]
256 4. **Support Tickets**: [e.g., "User submitted 3+ bug reports"]
257 5. **Payment Issues**: [e.g., "Credit card declined, didn't update"]
258 6. **No Activity in X Days**: [e.g., "No login in 14+ days"]
259
260 **Your At-Risk Criteria** (choose 3-5):
261 1. [Indicator 1] — e.g., "No login in 14 days"
262 2. [Indicator 2] — e.g., "Session frequency dropped >50%"
263 3. [Indicator 3] — e.g., "Didn't use core feature in last 30 days"
264
265 **At-Risk User Count**:
266 - Total Active Users: [X]
267 - At-Risk Users (meeting 2+ criteria): [Y]
268 - % At Risk: [Z%]
269
270 ---
271
272 **Question CP2: What is your plan to re-engage at-risk users?**
273
274 **Win-Back Campaign** (multi-channel, escalating touchpoints):
275
276 ### Tier 1: Subtle Re-Engagement (Days 7-14 inactive)
277 - **Email 1**: "We miss you! Here's what's new" (feature updates, product improvements)
278 - **In-App Notification**: "You haven't logged in recently. Come back for [incentive]"
279 - **Push Notification** (if mobile app): "Your [X] is waiting for you"
280
281 ### Tier 2: Value Reminder (Days 15-21 inactive)
282 - **Email 2**: "Remember why you signed up? Here's how [Product] helps with [pain point]"
283 - **Case Study**: "How [Customer Name] achieved [result] with [Product]"
284 - **Personal Outreach** (for high-value users): CEO/CSM sends personal email
285
286 ### Tier 3: Incentive (Days 22-30 inactive)
287 - **Email 3**: "We'd love to have you back. Here's [discount/free month/bonus credits]"
288 - **Survey**: "What would bring you back? We're listening" (with incentive for completing)
289
290 ### Tier 4: Last Chance (Days 30+ inactive)
291 - **Email 4**: "Last chance to keep your data. Account will be deactivated in 7 days"
292 - **Phone Call** (for enterprise): CSM calls to understand churn reason and offer solutions
293
294 **Win-Back Channels** (choose 3-5):
295 - ☐ Email (sequence of 3-4 emails)
296 - ☐ In-app notifications
297 - ☐ Push notifications (mobile)
298 - ☐ SMS (high-value users only)
299 - ☐ Retargeting ads (Facebook, Google)
300 - ☐ Personal outreach (phone, LinkedIn)
301
302 **Win-Back Success Metrics**:
303 - **Open Rate**: [Target: >25%]
304 - **Click Rate**: [Target: >10%]
305 - **Reactivation Rate**: [Target: >5% of inactive users return]
306
307 ---
308
309 ### Churn Reasons & Exit Analysis
310
311 **Question CR1: Why do users churn?**
312
313 **Exit Survey** (trigger when user cancels or becomes inactive):
314
315 **Question 1**: Why are you leaving?
316 - ☐ Too expensive
317 - ☐ Didn't see value / wasn't using it
318 - ☐ Missing features I need
319 - ☐ Found a better alternative
320 - ☐ Too complicated / hard to use
321 - ☐ Poor customer support
322 - ☐ Technical issues / bugs
323 - ☐ Other: [open text]
324
325 **Question 2**: What would have kept you as a customer?
326 - [Open text]
327
328 **Question 3**: Would you consider returning in the future?
329 - ☐ Yes, if [condition]
330 - ☐ No
331
332 **Churn Reason Breakdown** (based on exit surveys + data analysis):
333
334 | Churn Reason | % of Churned Users | Addressable? | Action Plan |
335 |---------------------------------|--------------------|--------------|---------------------------------------------|
336 | Didn't see value / low usage | X% | ✅ Yes | Improve onboarding, activation |
337 | Too expensive | X% | ✅ Yes | Introduce lower-tier plan, annual discount |
338 | Missing features | X% | ✅ Yes | Build top-requested features |
339 | Found better alternative | X% | ⚠️ Maybe | Competitive analysis, differentiate |
340 | Too complicated | X% | ✅ Yes | Simplify UI, improve help docs |
341 | Poor support | X% | ✅ Yes | Hire more support, reduce response time |
342 | Technical issues | X% | ✅ Yes | Fix bugs, improve performance |
343 | Company shut down / no longer needed | X% | ❌ No | Unavoidable churn |
344
345 **Top 3 Addressable Churn Reasons**:
346 1. [Reason 1] — [Action plan]
347 2. [Reason 2] — [Action plan]
348 3. [Reason 3] — [Action plan]
349
350 ---
351
352 **Question CR2: How can you reduce involuntary churn?**
353
354 **Involuntary Churn** = Users who churn due to failed payments (not because they wanted to leave)
355
356 **Payment Failure Reasons**:
357 - Expired credit card
358 - Insufficient funds
359 - Bank decline (fraud alert)
360 - Card changed (lost/stolen)
361
362 **Dunning Campaign** (recover failed payments):
363
364 ### Failed Payment Day 0:
365 - **Email 1**: "Payment failed. Please update your payment method" (link to billing page)
366 - **In-app banner**: "Action required: Update payment method"
367
368 ### Day 3:
369 - **Email 2**: "Reminder: Your payment failed. Update card to keep access"
370 - **Grace period**: Keep product access for 7-14 days
371
372 ### Day 7:
373 - **Email 3**: "Final reminder: Update payment or service will be suspended in 3 days"
374 - **SMS** (optional): "Your [Product] account will be suspended. Update payment now"
375
376 ### Day 10:
377 - **Suspend Service**: Downgrade to free plan or suspend account
378 - **Email 4**: "Account suspended. Update payment to restore access"
379
380 **Smart Dunning Tactics**:
381 - **Retry Schedule**: Retry failed payment 3 times (Day 0, Day 3, Day 7)
382 - **Alternative Payment Methods**: Offer PayPal, bank transfer, crypto
383 - **Update Card Before Expiry**: Email users 30 days before card expires
384
385 **Involuntary Churn Rate**:
386 - Current: [X% of total churn]
387 - Target: [<20% of total churn]
388
389 ---
390
391 ### Retention Loops & Product Improvements
392
393 **Question RL1: What retention loops can you build?**
394
395 **Retention Loop** = A repeating cycle that brings users back to the product
396
397 **Examples**:
398
399 1. **Content Drip Loop** (e.g., Duolingo, Netflix)
400 - New content released regularly (daily lessons, weekly episodes)
401 - Push notification: "Your [new content] is ready"
402 - User returns → consumes content → waits for next drop
403
404 2. **Social Loop** (e.g., LinkedIn, Facebook)
405 - User posts content
406 - Followers engage (likes, comments)
407 - Push notification: "[Friend] commented on your post"
408 - User returns → engages → posts again
409
410 3. **Progress Loop** (e.g., Strava, MyFitnessPal)
411 - User logs progress (workout, meal, habit)
412 - App shows streaks, achievements, leaderboards
413 - User returns to maintain streak → logs progress → cycle continues
414
415 4. **Collaboration Loop** (e.g., Slack, Figma, Notion)
416 - User invites team members
417 - Team collaborates in product
418 - Notifications: "[@mention] left a comment"
419 - User returns → collaborates → cycle continues
420
421 5. **Email Digest Loop** (e.g., Substack, Reddit)
422 - User subscribes to digest (daily, weekly)
423 - Email: "Here's what you missed this week"
424 - User clicks → returns to product → subscribes again
425
426 **Your Retention Loop(s)** (choose 1-3):
427 1. **[Loop Type]**: [How it works — trigger → action → return]
428 2. **[Loop Type]**: [How it works]
429 3. **[Loop Type]**: [How it works]
430
431 **Implementation Plan**:
432 - Loop 1: [What needs to be built? Timeline?]
433 - Loop 2: [What needs to be built? Timeline?]
434
435 ---
436
437 **Question RL2: What product improvements will reduce churn?**
438
439 **Churn-Reducing Product Changes** (based on churn reasons and user feedback):
440
441 | Churn Reason | Product Improvement | Priority | Timeline |
442 |----------------------------------|-------------------------------------------------------|----------|----------|
443 | "Didn't see value / low usage" | Improve onboarding, add activation checklist | High | 4 weeks |
444 | "Missing feature X" | Build feature X (top-requested) | High | 8 weeks |
445 | "Too complicated" | Simplify UI, add tooltips, create video tutorials | Medium | 6 weeks |
446 | "Technical issues" | Fix top 5 bugs, improve performance | High | 2 weeks |
447 | "Poor support" | Hire 2 support reps, reduce response time to <2 hours| Medium | 4 weeks |
448
449 **Quick Wins** (implement in next 30 days):
450 1. [Improvement 1] — e.g., "Add onboarding checklist (3 tasks to activation)"
451 2. [Improvement 2] — e.g., "Fix top 3 bugs causing user frustration"
452 3. [Improvement 3] — e.g., "Send weekly email digest to inactive users"
453
454 **Long-Term Bets** (implement in next 90 days):
455 1. [Improvement 1] — e.g., "Build top-requested feature (X)"
456 2. [Improvement 2] — e.g., "Redesign core workflow to reduce friction"
457 3. [Improvement 3] — e.g., "Add social features (commenting, sharing)"
458
459 ---
460
461 ### Customer Success Strategy
462
463 **Question CS1: What is your customer success strategy?**
464
465 **Customer Success Model** (choose based on ARPU and scale):
466
467 | ARPU | Model | CS Ratio | Touchpoints |
468 |---------------|------------------------------|-------------------|--------------------------------------------------|
469 | <$100/mo | **Tech-Touch** (automated) | 1 CSM : ∞ users | Email, in-app, chatbot, self-service resources |
470 | $100-$500/mo | **Hybrid** (light-touch) | 1 CSM : 100-200 | Quarterly check-ins, email, webinars, resources |
471 | $500-$2k/mo | **High-Touch** (proactive) | 1 CSM : 50-100 | Monthly QBRs, onboarding, ongoing support |
472 | >$2k/mo | **White-Glove** (dedicated) | 1 CSM : 10-30 | Dedicated CSM, weekly check-ins, custom success plan |
473
474 **Your Model**: [Tech-Touch / Hybrid / High-Touch / White-Glove]
475
476 **Customer Success Touchpoints**:
477
478 ### Onboarding (Days 0-30):
479 - **Day 0**: Welcome email + onboarding checklist
480 - **Day 3**: Check-in email: "How's onboarding going? Need help?"
481 - **Day 7**: Onboarding call (high-touch) or webinar (light-touch)
482 - **Day 14**: Feature tutorial: "Here's how to use [power feature]"
483 - **Day 30**: Success check-in: "Did you achieve [goal]?"
484
485 ### Ongoing Success (Month 2+):
486 - **Monthly**: Usage report: "Here's your activity this month"
487 - **Quarterly**: QBR (Quarterly Business Review) — review goals, usage, ROI
488 - **Ad Hoc**: Trigger-based outreach (e.g., usage drops, feature launch, renewal coming up)
489
490 ### Renewal/Expansion (30-60 days before renewal):
491 - **Renewal campaign**: "Your contract renews in 60 days. Let's review value delivered"
492 - **Expansion conversation**: "You're using X feature heavily. Have you considered Y feature?"
493
494 **Customer Health Score** (predict churn risk):
495
496 | Factor | Weight | Healthy | At Risk | Churn Risk |
497 |-------------------------------|--------|---------|---------|------------|
498 | Login Frequency | 30% | 10+ /mo | 3-9 /mo | <3 /mo |
499 | Feature Usage (core features) | 25% | 80%+ | 40-79% | <40% |
500 | Support Tickets (open) | 15% | 0-1 | 2-3 | 4+ |
501 | NPS Score | 15% | 9-10 | 7-8 | 0-6 |
502 | Payment Status | 15% | Current | Late | Failed |
503
504 **Health Score Calculation**:
505 - **Green (80-100)**: Healthy, potential for expansion
506 - **Yellow (50-79)**: At risk, requires proactive outreach
507 - **Red (<50)**: Churn risk, urgent intervention
508
509 **Current Health Score Distribution**:
510 - Green: [X%] of customers
511 - Yellow: [Y%] of customers
512 - Red: [Z%] of customers
513
514 ---
515
516 **Question CS2: How will you scale customer success?**
517
518 **Scaling Customer Success** (as you grow from 100 → 1,000 → 10,000 customers):
519
520 ### Phase 1: Manual (0-100 customers)
521 - **1 CSM** handles all customers
522 - Personal touch: emails, calls, QBRs
523 - Learn what works, document best practices
524
525 ### Phase 2: Semi-Automated (100-1,000 customers)
526 - **Segment customers** (high-value = high-touch, low-value = tech-touch)
527 - **Automate touchpoints** (email sequences, in-app messages, webinars)
528 - **Hire 2-3 CSMs** for high-value accounts
529
530 ### Phase 3: Fully Scaled (1,000+ customers)
531 - **CSM team by segment**: Enterprise (white-glove), Mid-Market (high-touch), SMB (tech-touch)
532 - **Self-service resources**: Help center, video tutorials, community forum
533 - **Proactive monitoring**: Health score dashboard, automated alerts for at-risk accounts
534
535 **Your Scaling Plan**:
536 - Current customer count: [X]
537 - Current CSM count: [Y]
538 - Next hire milestone: [When you reach Z customers, hire CSM #N]
539
540 ---
541
542 ### Implementation Roadmap
543
544 **Question IR1: What is your 90-day retention optimization plan?**
545
546 ### Phase 1: Analyze (Weeks 1-3)
547 **Goal**: Understand why users churn and identify at-risk segments
548
549 - **Week 1: Cohort Analysis**
550 - Pull cohort retention data (M0, M1, M3, M6, M12)
551 - Identify best-retaining and worst-retaining cohorts
552 - Segment retention by acquisition source, user persona, plan tier
553
554 - **Week 2: Churn Reason Analysis**
555 - Implement exit survey (trigger on cancellation)
556 - Interview 10-20 churned users (qualitative insights)
557 - Categorize churn reasons (addressable vs. unavoidable)
558
559 - **Week 3: At-Risk User Identification**
560 - Define at-risk criteria (3-5 leading indicators)
561 - Build at-risk user list (dashboard or export)
562 - Calculate health scores for all active users
563
564 **Deliverable**: Retention analysis report with top 3 churn drivers and at-risk user list
565
566 ---
567
568 ### Phase 2: Intervene (Weeks 4-6)
569 **Goal**: Launch win-back campaigns and reduce involuntary churn
570
571 - **Week 4: Win-Back Campaign**
572 - Build 4-email win-back sequence (Days 7, 14, 21, 30 inactive)
573 - Set up automated triggers (email service provider)
574 - Launch campaign for currently inactive users
575
576 - **Week 5: Dunning Campaign**
577 - Build dunning email sequence (payment failed → 3 reminders → suspend)
578 - Set up retry schedule (retry 3x over 10 days)
579 - Launch campaign for users with failed payments
580
581 - **Week 6: Personal Outreach (High-Value Users)**
582 - Identify top 20% of at-risk users by revenue
583 - Assign CSM to reach out (email, call, or LinkedIn)
584 - Offer solutions: feature training, discount, custom plan
585
586 **Deliverable**: Win-back and dunning campaigns live, 20% of at-risk high-value users contacted
587
588 ---
589
590 ### Phase 3: Improve Product (Weeks 7-12)
591 **Goal**: Build retention loops and fix top churn drivers
592
593 - **Week 7-8: Quick Wins**
594 - Implement onboarding checklist (improve activation)
595 - Fix top 3 bugs causing churn
596 - Add email digest (weekly summary for inactive users)
597
598 - **Week 9-10: Retention Loop**
599 - Design retention loop (content drip, social, progress, collaboration)
600 - Build loop triggers and notifications
601 - Launch loop to 10% of users (A/B test)
602
603 - **Week 11-12: Feature Improvements**
604 - Build top-requested feature (reduces "missing feature" churn)
605 - Simplify core workflow (reduces "too complicated" churn)
606 - Improve performance (reduces "technical issues" churn)
607
608 **Deliverable**: Retention loop live, top churn drivers addressed via product improvements
609
610 ---
611
612 ### Phase 4: Monitor & Iterate (Ongoing)
613 **Goal**: Track retention metrics and continuously optimize
614
615 - **Weekly**: Review at-risk user list, reach out to red-health-score users
616 - **Monthly**: Review cohort retention, churn rate, win-back campaign performance
617 - **Quarterly**: Deep dive into churn reasons, prioritize product improvements
618
619 **Success Metrics** (track over 90 days):
620 - **D30 Retention**: [Baseline → Target — e.g., 35% → 45%]
621 - **Churn Rate**: [Baseline → Target — e.g., 8% → 5%]
622 - **Win-Back Reactivation Rate**: [Target: 5-10% of inactive users return]
623 - **Involuntary Churn**: [Baseline → Target — e.g., 30% of churn → <20% of churn]
624 - **Health Score**: [% of users in Green — e.g., 60% → 75%]
625
626 ---
627
628 ## STEP 4: Generate Comprehensive Retention Optimization Strategy
629
630 **You will now receive a comprehensive document covering**:
631
632 ### Section 1: Executive Summary
633 - Current retention performance (D1/D7/D30, churn rate)
634 - Retention curve shape and critical drop-off points
635 - Top 3 churn drivers and action plans
636
637 ### Section 2: Cohort Analysis Deep Dive
638 - Cohort retention table (M0, M1, M3, M6, M12)
639 - Cohort improvement trend (improving, flat, declining)
640 - Segment retention comparison (by persona, acquisition source, plan tier)
641 - Best-retaining and worst-retaining segments
642
643 ### Section 3: Churn Prediction & At-Risk Users
644 - At-risk user criteria (3-5 leading indicators)
645 - At-risk user count and % of user base
646 - Customer health score model (5 factors, weighted)
647 - Health score distribution (Green, Yellow, Red)
648
649 ### Section 4: Win-Back & Dunning Campaigns
650 - **Win-Back Campaign**: 4-tier email sequence (Days 7, 14, 21, 30 inactive)
651 - **Dunning Campaign**: Payment failure recovery (Day 0, 3, 7, 10)
652 - Win-back channels (email, in-app, push, SMS, retargeting, personal outreach)
653 - Success metrics (open rate, click rate, reactivation rate)
654
655 ### Section 5: Churn Reason Analysis
656 - Exit survey questions (3 key questions)
657 - Churn reason breakdown (% of churned users, addressable?, action plan)
658 - Top 3 addressable churn reasons with action plans
659 - Involuntary churn strategy (dunning, grace period, alternative payments)
660
661 ### Section 6: Retention Loops & Product Improvements
662 - **Retention Loops** (1-3 loops: content drip, social, progress, collaboration, email digest)
663 - **Quick Wins** (implement in 30 days: onboarding checklist, bug fixes, email digest)
664 - **Long-Term Bets** (implement in 90 days: build top feature, redesign workflow, add social features)
665
666 ### Section 7: Customer Success Strategy
667 - Customer success model (tech-touch, hybrid, high-touch, white-glove)
668 - Touchpoints (onboarding Days 0-30, ongoing success, renewal/expansion)
669 - Customer health score calculation (5 factors, Green/Yellow/Red)
670 - Scaling plan (manual → semi-automated → fully scaled)
671
672 ### Section 8: Implementation Roadmap
673 - **Phase 1 (Weeks 1-3)**: Cohort analysis, churn reason analysis, at-risk user identification
674 - **Phase 2 (Weeks 4-6)**: Win-back campaign, dunning campaign, personal outreach
675 - **Phase 3 (Weeks 7-12)**: Quick wins, retention loop, feature improvements
676 - **Phase 4 (Ongoing)**: Monitor metrics, weekly/monthly/quarterly reviews
677
678 ### Section 9: Success Metrics
679 - D30 Retention: [Baseline → Target]
680 - Churn Rate: [Baseline → Target]
681 - Win-Back Reactivation Rate: [Target: 5-10%]
682 - Involuntary Churn: [<20% of total churn]
683 - Health Score: [75%+ of users in Green]
684
685 ### Section 10: Next Steps
686 - Launch win-back campaign this week
687 - Schedule monthly retention review meetings
688 - Integrate with **customer-feedback-framework** (use exit surveys to gather churn reasons)
689 - Integrate with **onboarding-flow-optimizer** (improve early retention via better activation)
690
691 ---
692
693 ## STEP 5: Quality Review & Iteration
694
695 After generating the strategy, I will ask:
696
697 **Quality Check**:
698 1. Is the retention baseline and target realistic? (D30 retention 35% → 45% in 90 days is achievable)
699 2. Are churn reasons based on real data (exit surveys, user interviews)?
700 3. Are at-risk criteria measurable and actionable?
701 4. Is the win-back campaign multi-channel and escalating?
702 5. Are retention loops feasible to build in the given timeline?
703 6. Is the customer success model appropriate for your ARPU and scale?
704
705 **Iterate?** [Yes — refine X / No — finalize]
706
707 ---
708
709 ## STEP 6: Save & Next Steps
710
711 Once finalized, I will:
712 1. **Save** the retention optimization strategy to your project folder
713 2. **Suggest** running **onboarding-flow-optimizer** next (to improve early retention)
714 3. **Remind** you to launch the win-back campaign this week
715
716 ---
717
718 ## 8 Critical Guidelines for This Skill
719
720 1. **Retention > Acquisition**: It's 5-7x cheaper to retain a customer than acquire a new one. Prioritize retention over growth.
721
722 2. **Cohort analysis is essential**: Don't just track overall retention. Track by cohort (signup month) and segment (persona, acquisition source, plan tier).
723
724 3. **At-risk users can be saved**: Identify users showing declining engagement 2-4 weeks before they churn, and intervene proactively.
725
726 4. **Involuntary churn is addressable**: 20-40% of churn is due to failed payments. Implement dunning campaigns to recover revenue.
727
728 5. **Exit surveys are mandatory**: You can't fix churn if you don't know why users leave. Trigger exit surveys on cancellation.
729
730 6. **Retention loops > one-time campaigns**: Build repeating cycles (content drip, social, progress) that bring users back automatically.
731
732 7. **Health scores predict churn**: Track 5 factors (login frequency, feature usage, support tickets, NPS, payment status) to calculate customer health.
733
734 8. **Customer success scales with ARPU**: Low ARPU = tech-touch (automated). High ARPU = high-touch (dedicated CSM).
735
736 ---
737
738 ## Quality Checklist (Before Finalizing)
739
740 - [ ] Retention baseline and targets are clearly defined (D1/D7/D30, churn rate)
741 - [ ] Cohort analysis shows retention by signup month and user segment
742 - [ ] At-risk user criteria are measurable (3-5 leading indicators)
743 - [ ] Win-back campaign is multi-channel with 4 touchpoints (Days 7, 14, 21, 30)
744 - [ ] Dunning campaign is implemented to reduce involuntary churn
745 - [ ] Top 3 churn reasons are identified with action plans
746 - [ ] 1-3 retention loops are defined (content drip, social, progress, collaboration, email digest)
747 - [ ] Customer success model matches your ARPU and scale
748 - [ ] Implementation roadmap is realistic (Weeks 1-3: Analyze, Weeks 4-6: Intervene, Weeks 7-12: Improve)
749 - [ ] Success metrics are tracked (D30 retention, churn rate, win-back reactivation, involuntary churn, health score)
750
751 ---
752
753 ## Integration with Other Skills
754
755 **Upstream Skills** (reuse data from):
756 - **metrics-dashboard-designer** → Retention metrics, cohort data, churn rates, health scores
757 - **customer-persona-builder** → User segments for cohort analysis
758 - **product-positioning-expert** → Value delivered, success indicators
759 - **onboarding-flow-optimizer** → Activation rates, early retention data
760 - **customer-feedback-framework** → Churn reasons, exit surveys, NPS, CSAT
761 - **email-marketing-architect** → Win-back email sequences, drip campaigns
762 - **growth-hacking-playbook** → Retention loops (AARRR framework)
763
764 **Downstream Skills** (use this data in):
765 - **customer-feedback-framework** → Gather feedback from churned users and at-risk users
766 - **onboarding-flow-optimizer** → Improve early retention (D1-D7) via better onboarding and activation
767 - **product roadmap** → Prioritize features that reduce churn (top-requested features, bug fixes)
768 - **investor-pitch-deck-builder** → Use improved retention metrics in traction slides
769 - **financial-model-architect** → Use lower churn rate to project revenue and LTV
770
771 ---
772
773 ## HTML Output Verification
774
775 After generating the HTML report, verify all elements render correctly:
776
777 ### Visual Verification Checklist
778 - [ ] Header displays business name and date correctly
779 - [ ] Score banner shows D30 retention, D7 retention, churn rate, at-risk %, healthy %
780 - [ ] Curve type verdict box displays correctly
781 - [ ] Retention curve container shows type and description
782 - [ ] Cohort table displays 4+ rows with color-coded retention cells
783 - [ ] Segment cards show 3-4 segments with metrics
784 - [ ] Risk indicators display 4-5 at-risk criteria with icons
785 - [ ] Health score distribution shows green/yellow/red percentages
786 - [ ] Health factors list shows 5 weighted factors
787 - [ ] Win-back timeline displays 4 escalating tiers
788 - [ ] Churn table shows reasons with addressability badges
789 - [ ] Retention loops show 2-3 loop cards with cycle steps
790 - [ ] CS model displays name and ratio
791 - [ ] Touchpoints grid shows 3 phases
792 - [ ] All 4 charts render with correct data:
793 - Retention curve (line with fill)
794 - Cohort comparison (bar)
795 - Churn reasons (horizontal bar)
796 - Health score distribution (doughnut)
797 - [ ] Success metrics show 5 baseline -> target cards
798 - [ ] Roadmap displays 4 phases with tasks
799 - [ ] Footer shows StratArts branding
800
801 ### Data Quality Verification
802 - [ ] D30 retention is realistic (typically 20-50% for SaaS)
803 - [ ] Churn rate aligns with retention (if 38% D30 retention, expect 5-8% monthly churn)
804 - [ ] Cohort data shows trend (improving, flat, or declining)
805 - [ ] Health score distribution adds to 100%
806 - [ ] Win-back tiers escalate logically (Days 7 -> 14 -> 21 -> 30+)
807 - [ ] Churn reasons sum to ~100%
808 - [ ] CS model matches ARPU (low ARPU = tech-touch, high = dedicated)
809
810 ### Template Location
811 - Skeleton template: `html-templates/retention-optimization-expert.html`
812 - Test output: `skills/retention-metrics/retention-optimization-expert/test-template-output.html`
813
814 ---
815
816 **End of Skill**