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Customer Success

skill-samuelcastro-startup-skills-customer-success · by samuelcastro

Guide founders through customer success strategy including onboarding, support processes, churn prevention, and satisfaction measurement. Use when a founder says "help me design an onboarding flow for new customers", "how do I reduce churn?", "create an NPS survey for my product", "build a customer health scoring system", "help me set up a support ticketing process", "how to improve my customer s…

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$ agentstack add skill-samuelcastro-startup-skills-customer-success

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No issues found. Passed automated security review. · v0.1.0 How review works →

  • Prompt-injection patterns
  • Secret / credential exfiltration
  • Dangerous shell & filesystem operations
  • Untrusted network calls
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  • Filesystem access No
  • Shell / process execution No
  • Environment & secrets No
  • Dynamic code execution No

From automated source analysis of v0.1.0. “Used” means the capability is present in the source — more access means more to trust, not that it’s unsafe.

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About

Customer Success

Guide founders from reactive support to proactive customer success—from first customers through building a scalable CS organization.

Reference Files

  • references/onboarding.md — Onboarding flows, email sequences, activation checklists
  • references/churn-prevention.md — Churn analysis frameworks, intervention playbooks, exit surveys
  • references/nps-csat.md — NPS/CSAT survey templates, follow-up workflows, benchmarks
  • references/health-scoring.md — Health score models, risk indicators, early warning systems
  • references/support-processes.md — Support ticketing, escalation paths, QBR templates

Workflow

1. Diagnose Stage & Need

Ask: "Where are you in your customer success journey?"

| Stage | Signals | Focus | |-------|---------|-------| | Early-stage (1-100 customers) | Founder handles support, no formal processes | → Lightweight onboarding, manual health checks | | Growth (100-500 customers) | Can't personally know every customer | → Systematize onboarding, implement health scoring | | Scale (500+ customers) | Building CS team, need playbooks | → Full CS org, automation, QBRs |

Primary Need Identification:

| Need | Signals | Next Step | |------|---------|-----------| | Onboarding | "Customers don't activate", "time to value is long" | → Step 2: Onboarding | | Churn | "Customers leaving", "high churn rate", "why are we losing customers?" | → Step 3: Churn Prevention | | Satisfaction | "Need NPS", "measure satisfaction", "customer feedback" | → Step 4: NPS & CSAT | | Health Scoring | "Predict at-risk customers", "proactive CS" | → Step 5: Health Scoring | | Support | "Support process", "ticketing", "QBRs" | → Step 6: Support & QBRs |

2. Onboarding

Transform new customers into successful, activated users. See references/onboarding.md for complete templates.

Onboarding Framework

The Goal: Deliver first value as fast as possible.

Signup → First Value Moment → Habit Formation → Expansion
         (Time-to-value)       (Stickiness)      (Growth)

Define Your Activation Moment:

| Business Type | Typical Activation | Why | |---------------|-------------------|-----| | B2B SaaS | First workflow completed | Core value realized | | Collaboration tool | Team member invited | Network effect | | Analytics | First report generated | Insight delivered | | Marketplace | First transaction | Both sides connected |

Onboarding Stages

| Stage | Goal | Timeframe | Key Actions | |-------|------|-----------|-------------| | Welcome | Set expectations | Day 0 | Welcome email, account setup | | Setup | Configure product | Day 1-3 | Core settings, integrations | | Activation | Reach first value | Day 3-7 | Guided workflow, first success | | Engagement | Build habit | Day 7-30 | Feature education, check-ins | | Expansion | Deepen usage | Day 30+ | Advanced features, team growth |

Stage-Appropriate Onboarding

Early-Stage (Manual, High-Touch):

  • Personal welcome call for every customer
  • White-glove setup assistance
  • Direct founder/CEO communication
  • Learn what customers actually need

Growth (Hybrid):

  • Self-serve for SMB, high-touch for enterprise
  • Automated email sequences with personal check-ins
  • In-app guidance (tooltips, checklists)
  • Segment by customer size/value

Scale (Automated with Exceptions):

  • Fully automated self-serve onboarding
  • Tech-touch for most, high-touch for strategic accounts
  • CSM assignment based on ARR threshold
  • Onboarding metrics dashboard
Onboarding Email Sequence

| Email | Timing | Purpose | Key Elements | |-------|--------|---------|--------------| | Welcome | Immediately | Confirm, set expectations | Login link, what's next, support contact | | Quick Win | Day 1 | Drive first action | One specific task to complete | | Setup Help | Day 3 | Remove friction | Common setup issues, FAQ link | | Activation Push | Day 5 | Drive to value moment | "Here's what successful users do first" | | Check-in | Day 7 | Personal touch | "How's it going? Questions?" | | Feature Intro | Day 14 | Deepen engagement | One underused feature | | Success Story | Day 21 | Social proof | Customer similar to them | | Expansion | Day 30 | Grow usage | Team features, advanced use cases |

Onboarding Metrics

| Metric | Formula | Target | |--------|---------|--------| | Time to First Value | Days from signup to activation | 60% | | Onboarding Completion | Users completing all steps / Total signups | >80% | | Day 7 Retention | Active day 7 / Total signups | >40% (B2B) |

3. Churn Prevention

Stop customers before they leave. See references/churn-prevention.md for intervention playbooks.

Understanding Churn

Types of Churn:

| Type | Cause | Prevention | |------|-------|------------| | Voluntary | Customer decides to leave | Value delivery, engagement | | Involuntary | Payment failure | Dunning emails, payment recovery | | Downgrade | Reduced spend | Demonstrate value, right-size plans |

Churn Timing Patterns:

| When | Likely Cause | Intervention | |------|--------------|--------------| | First 30 days | Poor onboarding, no value found | Activation focus, onboarding calls | | At renewal | Didn't see ROI | QBR before renewal, value recap | | After price increase | Price/value mismatch | Communicate value, offer options | | After champion leaves | Relationship-dependent | Multi-thread contacts |

Churn Analysis Framework

Step 1: Calculate Churn Rate

Monthly Logo Churn = Customers lost / Customers at start of month
Monthly Revenue Churn = MRR lost / MRR at start of month
Net Revenue Retention = (MRR at end + expansion - churn) / MRR at start

Step 2: Segment Churn

Analyze churn by:

  • Customer segment (SMB/Mid/Enterprise)
  • Tenure (first 90 days vs. established)
  • Acquisition channel
  • Plan type
  • Use case / vertical

Step 3: Identify Patterns

| Question | What It Reveals | |----------|----------------| | When do they churn? | Onboarding vs. renewal problem | | Who churns? | Segment fit issues | | What predicts churn? | Leading indicators | | Why do they say they're leaving? | Root cause |

Churn Intervention Playbook

| Risk Level | Indicators | Action | Owner | |------------|------------|--------|-------| | Critical | Cancellation request, angry ticket | Same-day call, escalate | CS Leader | | High | Usage dropped >50%, no login 14+ days | Outreach within 24h | CSM | | Medium | Usage declining, support tickets up | Automated + personal touch | CSM/Automated | | Low | Minor engagement dip | Automated nurture | Automated |

Exit Survey

When customers churn, learn why:

Exit Survey Questions:

  1. What was your primary reason for canceling? (Required, single select)
  • Found a better alternative
  • Too expensive
  • Missing features we needed
  • Didn't use it enough
  • Poor customer support
  • Company/budget changes
  • Other
  1. What could we have done differently? (Optional, open text)
  1. Would you consider us again in the future? (Required, Yes/No/Maybe)
  1. How likely are you to recommend us to others? (NPS scale)

4. NPS & CSAT

Measure and improve customer satisfaction. See references/nps-csat.md for survey templates.

NPS (Net Promoter Score)

The Question: > "On a scale of 0-10, how likely are you to recommend [Product] to a friend or colleague?"

Scoring:

  • Promoters (9-10): Loyal enthusiasts who refer others
  • Passives (7-8): Satisfied but vulnerable to competition
  • Detractors (0-6): Unhappy customers who can damage brand

NPS Calculation:

NPS = % Promoters - % Detractors
Range: -100 to +100

NPS Benchmarks:

| NPS Score | Rating | Context | |-----------|--------|---------| | 70+ | World-class | Top companies (Apple, USAA) | | 50-69 | Excellent | Strong customer loyalty | | 30-49 | Good | Healthy, room to improve | | 0-29 | Needs work | More detractors than ideal | | Negative | Critical | Urgent action needed |

B2B SaaS NPS Benchmarks:

| Segment | Median | Top Quartile | |---------|--------|--------------| | SMB | 30 | 50+ | | Mid-market | 35 | 55+ | | Enterprise | 40 | 60+ |

CSAT (Customer Satisfaction Score)

The Question: > "How satisfied are you with [specific interaction/product]?"

Scale: 1-5 or 1-7

CSAT Calculation:

CSAT = (Satisfied responses / Total responses) × 100
"Satisfied" = top 2 scores (4-5 on 5-point scale)

When to Use Each:

| Metric | Best For | Timing | |--------|----------|--------| | NPS | Overall relationship, loyalty | Quarterly, after key milestones | | CSAT | Specific interactions | After support ticket, after onboarding | | CES | Ease of experience | After specific task completion |

NPS Survey Implementation

Timing Strategy:

| Trigger | Rationale | |---------|-----------| | Quarterly | Regular pulse on relationship | | Post-onboarding (Day 30) | Measure first impression | | Post-support resolution | Measure support quality | | Pre-renewal (60 days out) | Identify at-risk before too late |

Follow-up Questions (by segment):

For Promoters (9-10): > "What do you love most about [Product]?" > "Would you be open to leaving a review or being a reference?"

For Passives (7-8): > "What would make you rate us higher?" > "What's one thing we could improve?"

For Detractors (0-6): > "We're sorry to hear that. What's the main reason for your score?" > "What would it take to improve your experience?"

NPS Follow-up Workflow

| Segment | Response SLA | Action | Owner | |---------|--------------|--------|-------| | Detractors | 24 hours | Personal call, understand issue | CSM/CS Leader | | Passives | 48 hours | Email follow-up, gather feedback | CSM | | Promoters | 1 week | Thank you, referral/review ask | CSM/Marketing |

5. Customer Health Scoring

Predict and prevent churn before it happens. See references/health-scoring.md for detailed models.

Health Score Components

Build a composite score from multiple signals:

| Category | Weight | Signals | |----------|--------|---------| | Product Usage | 40% | Login frequency, feature adoption, breadth of use | | Engagement | 25% | Support tickets, NPS responses, event attendance | | Relationship | 20% | Executive sponsor, champion strength, multi-threading | | Financial | 15% | Payment history, contract value, expansion potential |

Simple Health Score Model

For Early-Stage (Spreadsheet-Based):

| Dimension | Red (0 pts) | Yellow (1 pt) | Green (2 pts) | |-----------|-------------|---------------|---------------| | Login Frequency | No login 14+ days | 1-2x/week | 3+ times/week | | Feature Adoption | Only 1 feature | 2-3 features | 4+ features | | Support Sentiment | Negative tickets | Neutral | Positive/none | | Stakeholder Access | No response | Single contact | Multi-contact | | NPS Score | Detractor | Passive | Promoter |

Score Interpretation:

  • 8-10: Healthy (Green)
  • 5-7: Needs attention (Yellow)
  • 0-4: At risk (Red)
Stage-Appropriate Health Scoring

Early-Stage (1-100 customers):

  • Manual health check spreadsheet
  • Gut feel + basic usage data
  • Review weekly with founder
  • Focus on learning patterns

Growth (100-500 customers):

  • Simple scoring model in CRM
  • Automated alerts for red accounts
  • Weekly health review meeting
  • Start documenting playbooks

Scale (500+ customers):

  • Automated health scoring platform
  • ML-based churn prediction
  • Real-time dashboards
  • Tiered response playbooks
Acting on Health Scores

| Health | Action | Frequency | Goal | |--------|--------|-----------|------| | Green | Expansion focus | Quarterly QBR | Grow and advocate | | Yellow | Engagement boost | Bi-weekly check-in | Return to green | | Red | Intervention | Immediate | Save or learn |

6. Support Processes & QBRs

Build support systems that scale. See references/support-processes.md for templates.

Support Tier Structure

| Tier | Handles | Response Time | Escalation | |------|---------|---------------|------------| | Tier 1 | FAQs, how-to, basic issues | 70% | | CSAT (Support) | Post-ticket satisfaction | >90% | | Ticket Volume per Customer | Tickets / Active customers | Decreasing trend |

QBR (Quarterly Business Review)

Purpose: Demonstrate value, align on goals, identify expansion.

QBR Agenda (60 min):

| Section | Time | Content | |---------|------|---------| | Business Update | 5 min | Their company news, priorities | | Usage & Value | 15 min | Metrics, ROI achieved | | Wins & Challenges | 10 min | What's working, what's not | | Product Roadmap | 10 min | Relevant upcoming features | | Goals & Action Plan | 15 min | Next quarter objectives | | Expansion Discussion | 5 min | Growth opportunities |

QBR Preparation Checklist:

  • [ ] Usage data and trends pulled
  • [ ] ROI/value metrics calculated
  • [ ] Support ticket summary reviewed
  • [ ] Renewal date confirmed
  • [ ] Expansion opportunities identified
  • [ ] Stakeholder list updated
  • [ ] Previous QBR action items reviewed
When to Start QBRs

| Customer Segment | QBR Frequency | Delivery | |------------------|---------------|----------| | Enterprise ($100K+) | Quarterly | In-person or video | | Mid-market ($25-100K) | Bi-annually | Video call | | SMB (<$25K) | Annually or trigger-based | Email summary |

7. Building a CS Team

When to Hire First CSM:

  • [ ] 50+ customers
  • [ ] Founder can't personally manage all relationships
  • [ ] Churn is becoming a problem
  • [ ] Clear patterns in what makes customers successful

CSM-to-Account Ratios:

| Segment | Ratio | Why | |---------|-------|-----| | Enterprise | 1:10-20 | High-touch required | | Mid-market | 1:30-50 | Balanced touch | | SMB | 1:100-200 | Tech-touch + pooled |

First CS Hire Profile:

  • Previous startup experience at similar stage
  • Can build process, not just follow it
  • Strong communication + empathy
  • Comfortable with ambiguity
  • Technical enough to understand product

Deliverables

1. Onboarding Email Sequence

Create using docx skill:

  • 6-8 email sequence with timing
  • Subject lines and body copy
  • Personalization placeholders
  • Success metrics to track

2. Onboarding Checklist

Create using xlsx skill:

  • Step-by-step activation checklist
  • Owner assignments
  • Timeline targets
  • Completion tracking

3. Churn Analysis Framework

Create as markdown:

  • Churn calculation formulas
  • Segmentation dimensions
  • Analysis template
  • Intervention triggers

4. NPS Survey + Workflow

Create using docx skill:

  • Survey questions
  • Follow-up sequences by segment
  • Response SLAs
  • Reporting template

5. Customer Health Scorecard

Create using xlsx skill:

  • Scoring dimensions and weights
  • Red/yellow/green thresholds
  • Account list with scores
  • Action triggers

6. QBR Template

Create using pptx skill:

  • 8-10 slide deck template
  • Agenda and discussion guide
  • Metrics dashboard slide
  • Action plan format

7. Support Process Document

Create using docx skill:

  • Tier definitions and escalation paths
  • Response time SLAs
  • Ticket categorization
  • Metrics and reporting

Anti-Patterns

Onboarding Mistakes:

  • No defined activation moment (unclear success)
  • Same onboarding for all customers (one-size-fits-none)
  • Too many emails too fast (overwhelm)
  • No measurement (can't improve what you don't track)

Churn Prevention Mistakes:

  • Reactive only (waiting for cancellation request)
  • Not segmenting churn (treating all churn the same)
  • No exit interviews (missing root causes)
  • Focusing on save rate, not prevention

NPS Mistakes:

  • Survey fatigue (too frequent)
  • No follow-up on responses (especially detractors)
  • Gaming the score (

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

Install and usage instructions live in the source repository linked above.

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Versions

  • v0.1.0 Imported from the upstream source.