cs-strategist
Strategic Customer Success leadership guidance for CS org design, customer segmentation and tiering (tech touch, low touch, high touch), success metrics and KPIs (NRR, GRR, NPS, CSAT, CES), playbook development, executive stakeholder management, CS technology stack strategy, value realization frameworks, and customer journey mapping. Use when building CS teams, defining customer segments, designing playbooks, measuring success outcomes, or implementing CS platforms.
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Install
Works with every agent the skills CLI supports.
npx skills add https://github.com/ncklrs/startup-os-skills --skill cs-strategist- 01
Install
Run the command in your project. The CLI asks which agents to install for.
- 02
Describe the task
Ask your agent for something this skill covers. It loads cs-strategist automatically when relevant.
- 03
Review the result
The agent follows the SKILL.md steps, scripts and references bundled with the skill.
SKILL.md
The instructions your agent reads when the skill is triggered.
CS Strategist
Strategic Customer Success expertise for building and scaling world-class CS organizations — from team structure and segmentation to playbooks, metrics, and technology.
Philosophy
Customer Success is not support with a different name. It's a strategic function that drives predictable revenue growth through proactive customer value delivery.
The best CS organizations:
- Segment ruthlessly — One-size-fits-all is no-size-fits-any
- Measure outcomes, not activities — Calls made ≠ value delivered
- Scale before you hire — Technology enables, humans differentiate
- Own the number — CS owns Net Revenue Retention, full stop
How This Skill Works
When invoked, apply the guidelines in rules/ organized by:
org-*— CS org design, team structure, roles, hiringsegmentation-*— Customer tiering, coverage models, resource allocationmetrics-*— KPIs, health scores, forecasting, reportingplaybooks-*— Lifecycle playbooks, automation, QBRsexecutive-*— Stakeholder management, EBRs, C-level relationshipstechnology-*— CS platforms, tool stack, integrationvalue-*— Value realization, ROI frameworks, success plansjourney-*— Customer journey mapping, touchpoints, moments of truth
Core Frameworks
The CS Maturity Model
| Stage | Characteristics | Focus |
|---|---|---|
| Reactive | Support-driven, firefighting | Basic retention |
| Proactive | Health monitoring, early intervention | Churn prevention |
| Strategic | Outcome-focused, expansion-driven | NRR growth |
| Transformational | Customer value embedded in product | Market leadership |
Customer Segmentation Tiers
┌─────────────────────────────────────────────────────────┐
│ HIGH TOUCH │
│ Enterprise / Strategic accounts ($100k+ ARR) │
│ Dedicated CSM, EBRs, custom success plans │
│ Ratio: 1:10-25 accounts │
├─────────────────────────────────────────────────────────┤
│ LOW TOUCH │
│ Mid-market accounts ($15k-$100k ARR) │
│ Pooled CSMs, scaled programs, office hours │
│ Ratio: 1:50-100 accounts │
├─────────────────────────────────────────────────────────┤
│ TECH TOUCH │
│ SMB / Self-serve accounts (<$15k ARR) │
│ Automated journeys, community, self-service │
│ Ratio: 1:500+ accounts (or no dedicated CSM) │
└─────────────────────────────────────────────────────────┘
The CS Metrics Hierarchy
| Category | Metrics | Owner |
|---|---|---|
| Business Outcomes | NRR, GRR, Logo Retention | CS Leadership |
| Leading Indicators | Health Score, Adoption, NPS | CS Operations |
| Activity Metrics | Touchpoints, QBRs, Time-to-Value | CSMs |
Net Revenue Retention Formula
Starting MRR + Expansion - Contraction - Churn
NRR = ─────────────────────────────────────────────────── × 100
Starting MRR
Target NRR by segment:
- Enterprise: 115-130%+
- Mid-market: 105-115%
- SMB: 95-105%
The CS Tech Stack
| Layer | Function | Example Tools |
|---|---|---|
| Core Platform | Customer 360, health scores | Gainsight, ChurnZero, Totango |
| Data Layer | Product analytics, usage | Amplitude, Pendo, Mixpanel |
| Engagement | In-app, email automation | Intercom, Customer.io, Appcues |
| Feedback | Surveys, NPS | Delighted, Wootric, Satismeter |
| Intelligence | Churn prediction, next best action | Planhat, Catalyst |
Customer Journey Stages
PRE-SALES → ONBOARDING → ADOPTION → VALUE → EXPANSION → ADVOCACY
↓ ↓ ↓ ↓ ↓ ↓
Handoff Time-to- Feature Outcome Expansion Reference
Quality Value Adoption Achieved Opportunity Customer
The Value Realization Framework
| Phase | Definition | Deliverable |
|---|---|---|
| Define | Agree on success criteria | Success Plan |
| Deliver | Execute implementation & onboarding | Go-Live |
| Demonstrate | Prove value with metrics | Value Report |
| Develop | Expand usage and outcomes | Growth Plan |
Key Metrics Reference
| Metric | Definition | Good | Great |
|---|---|---|---|
| NRR | Net Revenue Retention | 105%+ | 120%+ |
| GRR | Gross Revenue Retention | 90%+ | 95%+ |
| Logo Retention | Customers retained | 85%+ | 92%+ |
| NPS | Net Promoter Score | 30+ | 50+ |
| CSAT | Customer Satisfaction | 4.0/5 | 4.5/5 |
| CES | Customer Effort Score | <3 | <2 |
| Time to Value | Days to first outcome | <30 | <14 |
| Health Score | Composite customer health | 70+ avg | 80+ avg |
Coverage Model Decision Framework
| Factor | High Touch | Low Touch | Tech Touch |
|---|---|---|---|
| ARR | $100k+ | $15k-100k | <$15k |
| Complexity | High | Medium | Low |
| Strategic Value | High potential | Standard | Transactional |
| Touch Frequency | Weekly-Monthly | Monthly-Quarterly | Automated |
| CSM Ratio | 1:10-25 | 1:50-100 | 1:500+ |
| Cost to Serve | 15-25% of ARR | 5-10% of ARR | <3% of ARR |
Anti-Patterns
- Measuring activities over outcomes — Calls logged ≠ customers retained
- One playbook for all segments — Tech touch playbooks for enterprise fail
- CS as support escalation — Reactive mode kills proactive capacity
- Health scores without action — Red accounts need intervention, not dashboards
- Siloed CS data — CS platform not integrated with CRM/Product
- CSM as single thread — Champion leaves, relationship collapses
- QBRs as PowerPoint theater — Value delivery, not presentation
- Ignoring tech touch — 80% of customers, 20% of attention
FAQ
What does the cs-strategist skill do?
Strategic Customer Success leadership guidance for CS org design, customer segmentation and tiering (tech touch, low touch, high touch), success metrics and KPIs (NRR, GRR, NPS, CSAT, CES), playbook development, executive stakeholder management, CS technology stack strategy, value realization frameworks, and customer journey mapping. Use when building CS teams, defining customer segments, designing playbooks, measuring success outcomes, or implementing CS platforms.
How do I install cs-strategist?
Run npx skills add https://github.com/ncklrs/startup-os-skills --skill cs-strategist in your project. The skills CLI detects the agents you use and copies the skill into the right folder. For Claude Code you can also place the skill folder at ~/.claude/skills/cs-strategist/ (personal) or .claude/skills/cs-strategist/ (project).
Which AI agents can use cs-strategist?
Any agent that supports the open Agent Skills format (a folder with a SKILL.md file), including Claude Code, Codex, Cursor, GitHub Copilot, Gemini CLI, Windsurf, Cline, OpenCode and more.
Is cs-strategist safe to install?
No partner security audit is available yet. Skills can run commands and scripts, so read the SKILL.md and any bundled files before installing.
Who maintains cs-strategist?
It is published by ncklrs in ncklrs/startup-os-skills. It has 143 recorded installs.
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