sales-customer-success

What this skill does

# Customer Success Strategy

Help the user design, optimize, and scale customer success programs — from building health scores and churn playbooks through onboarding optimization, expansion strategy, and CS platform selection.

## Step 1 — Gather context

If `references/learnings.md` exists, read it first for accumulated knowledge.

Ask the user:

1. **What do you need help with?**
   - A) Building or fixing a health score model
   - B) Reducing churn — understanding why customers leave
   - C) Onboarding — accelerating time-to-value for new customers
   - D) Expansion — upsell, cross-sell, identifying growth opportunities
   - E) CS playbooks — designing automated workflows for key moments
   - F) Choosing a CS platform (Vitally, Gainsight, ChurnZero, etc.)
   - G) CS metrics — NRR, GRR, logo retention, time-to-value
   - H) QBRs / business reviews — structure, cadence, content
   - I) Building/scaling a CS team — hiring, book-of-business, ratios
   - J) Something else — describe it

2. **What type of business?**
   - A) B2B SaaS (self-serve / PLG)
   - B) B2B SaaS (sales-led, mid-market)
   - C) B2B SaaS (enterprise, high-touch)
   - D) B2B services / consulting
   - E) Other

3. **Current CS tooling?** (Vitally, Gainsight, ChurnZero, Totango, spreadsheets, CRM-only, none)

4. **Customer count and ACV?** (Rough ranges: <50 customers, 50-500, 500-5000, 5000+; ACV: <$5K, $5-50K, $50-500K, $500K+)

**If the user's request already provides enough context, skip to the relevant step.** Lead with your best-effort answer, then ask 1-2 clarifying questions at the end.

## Step 2 — Route or answer directly

If the request maps to a platform-specific skill, route:
- Gainsight platform questions → `/sales-gainsight {your question}`
- Vitally platform questions → `/sales-vitally {your question}`
- Planhat platform questions → `/sales-planhat {your question}`
- ChurnZero platform questions → `/sales-churnzero {your question}`
- Totango platform questions → `/sales-totango {your question}`
- NPS/CSAT/CES survey methodology → `/sales-customer-feedback {your question}`
- Ecommerce visitor identity/retention → `/sales-retention {your question}`
- In-app messaging for onboarding → `/sales-in-app-messaging {your question}`
- Enterprise digital adoption (Whatfix) → `/sales-whatfix {your question}`
- CRM data quality for CS → `/sales-data-hygiene {your question}`

Otherwise, answer directly using the strategy guidance below.

## Step 3 — Customer success strategy

### Health score design

**The 4-metric framework** (start here, expand later):

| Category | What to measure | Signal type | Example indicators |
|---|---|---|---|
| **Product usage** | Are they using the product? | Leading | DAU/MAU ratio, key feature adoption, login frequency |
| **Engagement** | Are they talking to you? | Leading | Email opens, meeting attendance, support interactions |
| **Outcomes** | Are they getting value? | Lagging | Goal completion, ROI metrics, time-to-value |
| **Sentiment** | How do they feel? | Lagging | NPS score, CSAT trend, champion engagement |

**Weighting guidelines:**
- Weight product usage highest (40-50%) — it's the strongest churn predictor
- Don't weight NPS above 15-20% — it's a lagging indicator
- Adjust weights by segment — enterprise health depends more on champion engagement, PLG depends more on usage
- Don't change weights for 6-10 months after initial setup — you need stable data to validate

**Scoring model:**
- Use a 0-100 or 0-10 composite score
- Define thresholds: Green (healthy), Yellow (at-risk), Red (critical)
- Set thresholds based on actual churn data, not gut feel — run a retroactive analysis

### Churn prevention

**Early warning signals (by priority):**
1. **Champion leaves** — the single strongest churn predictor. Track job changes via LinkedIn/enrichment tools.
2. **Usage decline** — 20%+ drop in key feature usage over 2-4 weeks
3. **Support escalations** — increasing ticket volume or severity
4. **Engagement drop** — missing QBRs, not responding to emails, skipping training
5. **Contract/billing signals** — late payments, downgrade requests, procurement inquiries

**Response playbook by signal:**
| Signal | Response | Timeline |
|---|---|---|
| Champion left | Executive outreach + new champion identification | Within 48 hours |
| Usage declined 20%+ | CSM call + usage review + retraining offer | Within 1 week |
| Health score dropped to Yellow | Check-in email + value reaffirmation | Within 3 days |
| Health score dropped to Red | Executive sponsor escalation + save plan | Within 24 hours |
| Renewal < 90 days + Red health | Save team assembled (CS + Sales + Exec) | Immediately |

### Customer onboarding

**Time-to-value framework:**
1. **Define "first value"** — what's the moment the customer says "this is working"? Map it.
2. **Milestone-based progression** — don't use time-based milestones ("Week 2: do X"). Use outcome-based: "Complete when customer has sent their first campaign."
3. **Track onboarding health separately** — a new customer's health score is meaningless until they've activated. Use project completion % instead.

**Common onboarding stalls and fixes:**
- **Data migration stuck**: Offer white-glove migration for high-ACV accounts; self-serve import tools for low-ACV
- **Champion too busy**: Identify 2-3 stakeholders during kickoff, not just the champion
- **Technical blockers**: Engineering liaison on standby for first 30 days
- **No executive sponsor**: Get exec buy-in during handoff from sales

### Expansion revenue

**Expansion triggers:**
- Usage approaching plan limits (seats, API calls, storage)
- New department or team adopting the product
- Customer asking about features on higher tier
- Champion promoted (now has budget authority)
- Company raised funding or had strong earnings

**Expansion playbook:**
1. Identify the trigger signal (automated via CS platform or manual)
2. CSM validates the opportunity is real (not just a data blip)
3. Warm handoff to AE/AM with context package (usage data, stakeholder map, recommended package)
4. Joint call: CSM provides continuity, AE handles commercial

### CS platform comparison

| Platform | Best for | Pricing | Key strength |
|---|---|---|---|
| **Vitally** | Mid-market B2B SaaS, fast setup | Request pricing (3 tiers) | Modern UI, fast time-to-value, AI copilot |
| **Gainsight** | Enterprise, complex orgs | ~$30K+/year | Deepest feature set, Gartner #1 Leader |
| **ChurnZero** | Mid-market, real-time analytics | Custom | Customer Monitoring score (9.2/10), in-app engagement |
| **Totango** | Enterprise, quick implementation | ~$50K+/year | Modular SuccessBLOCs, quick deploy |
| **Custify** | SMB-mid, affordable | From ~$999/mo | Good value, lifecycle-focused |
| **Planhat** | Data-heavy teams | Custom | Strong data modeling, flexible health scores |

**Decision framework:**
- **< 50 customers, < $5K ACV**: Spreadsheets + CRM is fine. Don't buy a CS platform yet.
- **50-500 customers, $5-50K ACV**: Vitally or ChurnZero — fast setup, good mid-market fit
- **500+ customers, $50K+ ACV**: Gainsight or Totango — enterprise features, complex org support
- **PLG / tech-touch**: Vitally (Tech-Touch plan) or ChurnZero — automation-first design

### CS metrics

| Metric | Formula | Benchmark (B2B SaaS) | Why it matters |
|---|---|---|---|
| **NRR** (Net Revenue Retention) | (Start MRR + expansion - contraction - churn) / Start MRR | 100-120% | The single best CS metric — >100% means you grow even without new customers |
| **GRR** (Gross Revenue Retention) | (Start MRR - contraction - churn) / Start MRR | 85-95% | Shows retention without expansion masking churn |
| **Logo retention** | (Customers end - new) / Customers start | 85-95% | Raw customer count retention |
| **Time-to-value** | Days from contract signed to first value milestone | 14-60 days | Shorter = better retention + expansion |
| **CSAT / NPS** | Survey-based | NPS 30-50 | Sentiment indicator, not a target |

## Step 4 — Action