home / skills / ncklrs / startup-os-skills / cs-strategist

cs-strategist skill

Q: When should CS own NRR versus shared ownership?

CS should own NRR operationally with cross-functional partners (sales, product, finance) contributing; CS drives retention and expansion playbooks and reporting.

safe

/skills/cs-strategist

This skill helps design scalable CS organizations, segment customers, define playbooks, measure KPIs, and align technology to drive predictable revenue growth.

npx playbooks add skill ncklrs/startup-os-skills --skill cs-strategist

Review the files below or copy the command above to add this skill to your agents.

Files (12)

SKILL.md

7.0 KB

---
name: cs-strategist
description: 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.
---

# 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:
1. **Segment ruthlessly** — One-size-fits-all is no-size-fits-any
2. **Measure outcomes, not activities** — Calls made ≠ value delivered
3. **Scale before you hire** — Technology enables, humans differentiate
4. **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, hiring
- `segmentation-*` — Customer tiering, coverage models, resource allocation
- `metrics-*` — KPIs, health scores, forecasting, reporting
- `playbooks-*` — Lifecycle playbooks, automation, QBRs
- `executive-*` — Stakeholder management, EBRs, C-level relationships
- `technology-*` — CS platforms, tool stack, integration
- `value-*` — Value realization, ROI frameworks, success plans
- `journey-*` — 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

Overview

This skill delivers strategic Customer Success leadership guidance for designing CS orgs, segmentation, playbooks, KPIs, and technology strategy. It focuses on building predictable revenue through outcome-driven CS: clear tiers (tech/low/high touch), measurable success metrics, and scalable processes. Use it to create operating models that drive NRR, reduce churn, and scale before hiring.

How this skill works

When invoked, the skill applies a structured rule set across core domains: org design, segmentation, metrics, playbooks, exec engagement, technology, value realization, and journey mapping. It recommends customer tiers and coverage ratios, defines KPIs (NRR, GRR, NPS, CSAT, CES), and produces playbook and tooling suggestions tailored to segment economics. Outputs include role models, coverage decisions, metric targets, and a prioritized tech stack and implementation roadmap.

When to use it

Building or redesigning a CS organization and team structure
Defining customer segmentation, coverage models, and CSM ratios
Designing lifecycle playbooks, onboarding, and scaled automation
Setting CS metrics, forecasting, and reporting (NRR, GRR, health scores)
Selecting or rationalizing the CS technology stack
Preparing executive reporting, EBRs, or stakeholder engagement plans

Best practices

Segment ruthlessly by ARR, complexity, and strategic value; avoid one-size-fits-all playbooks
Measure outcomes (NRR, time-to-value) before activities; make health scores actionable
Scale with automation and tooling before adding headcount; humans focus on differentiated accounts
Own the number: CS is accountable for NRR and expansion motion
Design playbooks per tier: high touch = bespoke success plans; tech touch = automated journeys

Example use cases

Define a three-tier coverage model and recommended CSM ratios for a SaaS scale-up
Create KPI targets and a reporting dashboard for CS leadership focused on NRR and GRR
Design onboarding and time-to-value playbooks for mid-market accounts
Recommend a CS tech stack (customer 360, product analytics, engagement, feedback) and integration priorities
Build an executive reporting cadence and template for EBRs and quarterly reviews

FAQ

What NRR targets should I set by segment?

Aim for Enterprise 115–130%+, Mid-market 105–115%, SMB 95–105% as initial targets and adjust for your market dynamics.

How do I choose between low touch and tech touch?

Use ARR, complexity, and strategic value: <$15k and low complexity = tech touch; $15k–100k with moderate complexity = low touch.

When should CS own NRR versus shared ownership?

CS should own NRR operationally with cross-functional partners (sales, product, finance) contributing; CS drives retention and expansion playbooks and reporting.