Use this skill when building health scores, predicting churn, identifying expansion signals, or running QBRs. Triggers on customer success, health scores, churn prediction, expansion signals, customer QBRs, onboarding playbooks, NRR optimization, and any task requiring customer success strategy or operations.
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name
customer-success-playbook
version
0.1.0
description
Use this skill when building health scores, predicting churn, identifying expansion signals, or running QBRs. Triggers on customer success, health scores, churn prediction, expansion signals, customer QBRs, onboarding playbooks, NRR optimization, and any task requiring customer success strategy or operations.
When this skill is activated, always start your first response with the 🧢 emoji.
Customer Success Playbook
Customer Success (CS) is the discipline of ensuring customers achieve their
desired outcomes using your product - making churn prevention a byproduct of
genuine value delivery rather than a reactive damage-control function. This skill
covers the full CS operating model: health scoring, onboarding design, churn
prediction, expansion identification, QBR execution, segmentation, and team
performance measurement.
When to use this skill
Trigger this skill when the user:
Needs to build or improve a customer health scoring system
Wants to design or audit an onboarding playbook
Asks how to predict, detect, or prevent customer churn
Needs to identify expansion and upsell opportunities
Wants to run effective Quarterly Business Reviews (QBRs)
Asks how to segment customers by value or risk tier
Needs to define CS team KPIs or OKRs
Is working on NRR (Net Revenue Retention) or GRR (Gross Revenue Retention) improvement
Sales prospecting, lead scoring, or new logo acquisition (pre-sale belongs to sales enablement)
Key principles
Proactive, not reactive - CS that only responds to support tickets is account
management, not customer success. Intervene before customers feel pain. The best
save is the one that never needed saving.
Health scores drive action - A health score that lives in a dashboard but
never triggers a workflow is decoration. Every health band must have an associated
motion: what the CSM does, when, and how. Score without action is noise.
Onboarding determines lifetime value - The first 30-90 days set the trajectory
for the entire customer relationship. Customers who reach their first "aha moment"
quickly retain at 2-3x the rate of those who struggle. Invest disproportionately
in time-to-value.
Expansion is earned, not sold - Upsells from customers who haven't achieved
their desired outcomes produce churn, not growth. Expansion should follow proven
value, not quota pressure. The signal to expand is the customer asking for more,
not the CSM pitching more.
Segment by value and risk - Not all customers deserve the same coverage model.
High-ARR accounts need white-glove, human-led success. Low-ARR accounts need
scalable, tech-touch programs. Mismatching coverage to tier burns CSM capacity on
accounts that can't justify the cost and underserves accounts that need attention.
Core concepts
The CS lifecycle
Every customer moves through predictable phases, each with distinct success criteria:
Phase
Duration
Goal
Key risk
Onboarding
Days 1-90
First value realization
Slow time-to-value, scope creep
Adoption
Months 3-12
Broad, deep usage across team
Shallow single-user adoption
Renewal
90 days before renewal
Confirmed ROI, signed renewal
Surprise objections at renewal
Expansion
Post-renewal or milestone
Upsell based on proven value
Premature pitching
Advocacy
Ongoing
Reference, case study, promoter
Neglect after expansion
Health score components
A well-designed health score is a weighted composite of leading indicators that
predict renewal probability. Common dimensions and typical weights:
Design a weighted, multi-dimensional model that produces a single score (0-100) and
a color-coded band (Red / Yellow / Green) with automatic CSM action triggers.
Step 1 - Define dimensions and weights.
Select 4-6 dimensions relevant to your business. Product usage should carry the
highest weight (30-40%) because it is objective and hardest to fake.
Step 2 - Normalize each dimension to 0-100.
Map each raw metric to a 0-100 sub-score using thresholds. Example for usage:
Step 5 - Build a feedback loop. Compare health score 90 days prior to renewal
against actual renewal outcome. Tune weights until model achieves >75% predictive
accuracy for churn.
See references/health-score-model.md for the full scoring template.
Design an onboarding playbook
Onboarding ends when the customer achieves their first committed outcome, not when
technical setup is complete. Structure around milestones, not calendar dates.
Milestone 1 - Technical kickoff (Days 1-7)
Stakeholder alignment: map goals to product capabilities
Technical setup complete: integrations, SSO, data imports
Success plan signed: 3-5 measurable goals with target dates
Milestone 2 - First value realization (Days 14-30)
Core use case live with real data
At least 3 active users beyond the champion
Customer can demonstrate the product unaided
Milestone 3 - Team adoption (Days 30-60)
60% of licensed seats active
Secondary use case identified or live
Milestone 4 - Outcome confirmation (Days 60-90)
At least one success plan goal achieved or measurably progressing
EBR scheduled with executive sponsor
Expansion signals documented for account plan
Predict and prevent churn - early warning system
Tiered alert triggers:
Alert level
Trigger criteria
Response
Watch
Health score drops from Green to Yellow
CSM schedules check-in within 7 days
Warning
Yellow for 21+ days, or any single dimension at 0
CSM escalates, builds risk mitigation plan
Critical
Health score Red, OR champion departs, OR formal complaint
Executive engagement within 48 hours, save plan
Save plan template:
Root cause analysis - what drove the score down?
Executive alignment - is there internal will to stay?
Remediation actions - concrete steps with owners and dates
Success criteria - what does "saved" look like at 30/60/90 days?
Go/no-go checkpoint - if criteria not met, prepare graceful offboarding
Identify expansion opportunities - signals and timing
Qualification criteria before starting an expansion motion:
Health score Green for at least 60 consecutive days
At least one success plan goal achieved with documented ROI
Champion actively engaged
Renewal is not within 60 days
Expansion conversation framework:
Anchor to achieved value - reference a specific metric
Surface the adjacent pain - ask about problems the expanded product solves
Quantify the gap - help the customer estimate the cost of not solving it
Propose a pilot or phased expansion
Involve the AE for formal commercial motion; CSM does not own the close
Run effective QBRs - agenda
A QBR is a strategic alignment meeting, not a product demo. Target audience is
executive sponsors; goal is confirming strategic value and setting next-quarter direction.
QBR agenda (60 minutes):
Time
Section
Owner
0-5 min
Welcome and objectives
CSM
5-20 min
Results: goals vs. actuals from last quarter
CSM + Customer champion
20-30 min
Value realized: ROI story with business metrics
CSM
30-40 min
Challenges and open risks (honest)
Both sides
40-50 min
Goals and success criteria for next quarter
Customer executive
50-60 min
Product roadmap alignment + asks from customer
CSM + AE
Preparation checklist: Pull 90-day health score trend, document 2 quantified
ROI data points, prepare 3 success plan status updates, know the renewal date,
brief your exec sponsor, identify one expansion opportunity (if Green health).
Segment and tier CS coverage
Tier
ARR range
Coverage model
CSM ratio
Touchpoint cadence
Enterprise
>$100K
Named CSM, white-glove, proactive
1:10-20
Bi-weekly syncs, quarterly EBRs
Mid-Market
$20K-$100K
Named CSM, pooled for scale
1:40-80
Monthly syncs, semi-annual EBRs
SMB / Long Tail
<$20K
Tech-touch: automated email, in-app, community
1:200+
Automated lifecycle sequences
Measure CS team performance - metrics
Lagging metrics:
Metric
Definition
Target benchmark
Gross Revenue Retention (GRR)
Revenue retained excluding expansion
>90% for SaaS
Net Revenue Retention (NRR)
Revenue retained including expansion, minus churn
>110% signals healthy growth
Logo Churn Rate
% of customers lost in a period
<5% annually
Renewal Rate
% of renewals closed on time
>95%
Leading metrics:
Metric
Why it matters
Time-to-First-Value
Predicts long-term retention
Health Score Distribution
Portfolio risk visibility
QBR Completion Rate
Measures strategic engagement
Expansion Pipeline Coverage
Expansion predictability
Anti-patterns
Anti-pattern
Why it fails
What to do instead
Health score theater
Score exists in Salesforce but drives zero workflow
Tie every health band to a mandatory CSM action with SLA
One-size-fits-all coverage
Named CSMs on $5K accounts burns capacity; $500K accounts get neglected
Segment by ARR; build tech-touch for the long tail
Renewal-only QBRs
Signals the relationship is purely transactional
Run QBRs on a calendar cadence regardless of renewal timing
Premature expansion
Pitching upsells before first outcome produces churn, not revenue
Gate expansion on Green health (60+ days) and one achieved goal
Champion dependency
Single champion leaves and account collapses
Map at least two stakeholders; involve exec sponsor from onboarding
Vanity NPS
Sending surveys without acting on detractors
Close the loop on every detractor within 5 business days
Gotchas
Health score with no action trigger is decoration - A health score that lives in Salesforce and gets reviewed once a month during pipeline calls is not driving behavior. Every health band must have a mandatory CSM action with a defined SLA. Green without an expansion motion and Red without an escalation protocol are both failures of the system.
Champion departure is not always visible in usage data - Product usage can remain stable for 30-60 days after a champion leaves, because the remaining users keep using the product out of habit. The champion departure is a leading indicator that usage will decline. Monitor LinkedIn/CRM for job changes on key contacts, not just product telemetry.
Premature expansion pitches accelerate churn - Attempting to upsell a customer who has not yet achieved their primary success plan goals communicates that you care more about revenue than their outcomes. It damages trust, poisons renewal conversations, and produces contraction, not expansion. Gate expansion motions strictly on Green health for 60+ days and at least one documented ROI milestone.
QBR attendance without executive preparation - A QBR where the customer executive shows up cold (no agenda sent in advance, no pre-read, no briefing with the champion) quickly turns into a status update that could have been an email. Send the agenda and ROI data 5 business days in advance and pre-brief the champion on what you want the executive to walk away thinking.
Onboarding completion measured by setup, not value - Marking onboarding complete when technical setup is done (SSO configured, data imported) does not indicate the customer has achieved any business value. The real onboarding milestone is first value realization: a user has completed a meaningful workflow with real data and can demonstrate it unaided.
References
references/health-score-model.md - Detailed weighted health score model with
dimension definitions, normalization tables, and threshold calibration guidance
Only load the reference file when the task requires designing or auditing a health
scoring system in detail.
Companion check
On first activation of this skill in a conversation: check which companion skills are installed by running ls ~/.claude/skills/ ~/.agent/skills/ ~/.agents/skills/ .claude/skills/ .agent/skills/ .agents/skills/ 2>/dev/null. Compare the results against the recommended_skills field in this file's frontmatter. For any that are missing, mention them once and offer to install:
