ncklrs

cs-strategist

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# Install this skill:
npx skills add ncklrs/startup-os-skills --skill "cs-strategist"

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# 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.

# SKILL.md


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 β€” 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 β€” One-size-fits-all is no-size-fits-any
2. Measure outcomes, not activities β€” Calls made β‰  value delivered
3. Scale before you hire β€” Technology enables, humans differentiate
4. Own the number β€” CS owns Net Revenue Retention, full stop

How This Skill Works

When invoked, apply the guidelines in rules/ organized by:

  • org-* β€” CS org design, team structure, roles, hiring
  • segmentation-* β€” Customer tiering, coverage models, resource allocation
  • metrics-* β€” KPIs, health scores, forecasting, reporting
  • playbooks-* β€” Lifecycle playbooks, automation, QBRs
  • executive-* β€” Stakeholder management, EBRs, C-level relationships
  • technology-* β€” CS platforms, tool stack, integration
  • value-* β€” Value realization, ROI frameworks, success plans
  • journey-* β€” 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

β”Œβ”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”
β”‚                    HIGH TOUCH                           β”‚
β”‚  Enterprise / Strategic accounts ($100k+ ARR)           β”‚
β”‚  Dedicated CSM, EBRs, custom success plans              β”‚
β”‚  Ratio: 1:10-25 accounts                                β”‚
β”œβ”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€
β”‚                    LOW TOUCH                            β”‚
β”‚  Mid-market accounts ($15k-$100k ARR)                   β”‚
β”‚  Pooled CSMs, scaled programs, office hours             β”‚
β”‚  Ratio: 1:50-100 accounts                               β”‚
β”œβ”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€
β”‚                    TECH TOUCH                           β”‚
β”‚  SMB / Self-serve accounts (<$15k ARR)                  β”‚
β”‚  Automated journeys, community, self-service            β”‚
β”‚  Ratio: 1:500+ accounts (or no dedicated CSM)           β”‚
β””β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”€β”˜

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 = ─────────────────────────────────────────────────── Γ— 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 β†’ ONBOARDING β†’ ADOPTION β†’ VALUE β†’ EXPANSION β†’ 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 β€” Calls logged β‰  customers retained
  • One playbook for all segments β€” Tech touch playbooks for enterprise fail
  • CS as support escalation β€” Reactive mode kills proactive capacity
  • Health scores without action β€” Red accounts need intervention, not dashboards
  • Siloed CS data β€” CS platform not integrated with CRM/Product
  • CSM as single thread β€” Champion leaves, relationship collapses
  • QBRs as PowerPoint theater β€” Value delivery, not presentation
  • Ignoring tech touch β€” 80% of customers, 20% of attention

# Supported AI Coding Agents

This skill is compatible with the SKILL.md standard and works with all major AI coding agents:

Learn more about the SKILL.md standard and how to use these skills with your preferred AI coding agent.