sales-skills/sales-customer-success

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 — Actionable guidance

Focus on the user's specific situation. If you discover a tip not covered in references/learnings.md, append it there.

Gotchas

Best-effort from research — review these, especially items about CS metrics and platform capabilities that evolve quickly.

• Health scores are not a goal. "Improve our health score" is meaningless. Health scores are diagnostic — fix the underlying drivers (usage, engagement, outcomes) and the score follows.

• Don't automate empathy. Automated check-ins are fine for tech-touch. For high-touch accounts, a human CSM call always outperforms a template email when health drops.

• NRR masks churn. A company with 130% NRR but 75% GRR is growing on the backs of a few expanding accounts while bleeding customers. Track both.

• CS platforms need dedicated setup time. Vitally is ~2-4 weeks. Gainsight is ~2-6 months. Budget accordingly.

• Champion tracking is the most underrated CS activity. Most churn happens 3-6 months after a champion leaves. Build a process to detect and respond to champion departures.

• Self-improving: If you discover something not covered here, append it to references/learnings.md with today's date.

Before recommending a specific platform skill

This skill covers a strategy domain across many platforms. Before pointing the user to any specific platform skill (any /sales-{platform} listed in ## Related skills, e.g., /sales-mailshake, /sales-klaviyo, /sales-apollo), read that platform skill's actual SKILL.md first. The 1-line description in ## Related skills is enough to identify a candidate — it's not enough to commit to it or to write a prompt that invokes it well.

How to read it:

• If ~/.claude/skills/{skill-name}/SKILL.md exists locally, Read it.
• For sales-* skills, WebFetch directly from this repo: https://raw.githubusercontent.com/sales-skills/sales/main/skills/{skill-name}/SKILL.md — e.g., for sales-mailshake: https://raw.githubusercontent.com/sales-skills/sales/main/skills/sales-mailshake/SKILL.md.
• For non-sales-* skills (third-party), look up {org}/{repo} in ~/.claude/skills/sales-do/references/skill-sources.md if installed and fetch the same skills/{skill-name}/SKILL.md path under that repo.

After reading, ground your recommendation in something concrete from the SKILL.md (its scope, a sub-flow, its argument-hint shape, or a "Do NOT use for..." negative trigger). Align any generated invocation with the platform skill's argument-hint. If the platform skill turns out not to fit the user's situation, swap to another or handle the question here directly rather than recommending a poor fit.

Related skills

• /sales-vitally — Vitally platform help: Health Scores, Playbooks, Projects, API, integrations. Install: npx skills add sales-skills/sales --skill sales-vitally
• /sales-planhat — Planhat platform help: Health Scores, Revenue Management, CRM Sync, Automation, MCP Server, API. Install: npx skills add sales-skills/sales --skill sales-planhat
• /sales-churnzero — ChurnZero platform help: Health Scores, Plays, Journeys, Renewal Hub, In-App WalkThroughs, Surveys, AI Agents, API. Install: npx skills add sales-skills/sales --skill sales-churnzero
• /sales-gainsight — Gainsight platform help: CS health scores, CTAs, playbooks, success plans, Journey Orchestrator, PX, Staircase AI, Skilljar, API. Install: npx skills add sales-skills/sales --skill sales-gainsight
• /sales-customer-feedback — NPS, CSAT, CES, VoC program design — survey methodology, response rates, closed-loop feedback. Install: npx skills add sales-skills/sales --skill sales-customer-feedback
• /sales-in-app-messaging — In-app messages for onboarding tours, feature announcements, NPS surveys. Install: npx skills add sales-skills/sales --skill sales-in-app-messaging
• /sales-totango — Totango platform help: SuccessBLOCs, SuccessPlays, Health Scores, Customer Data Hub, Unison AI, Catalyst, API. Install: npx skills add sales-skills/sales --skill sales-totango
• /sales-coaching — Sales-to-CS handoff, coaching frameworks, onboarding reps. Install: npx skills add sales-skills/sales --skill sales-coaching
• /sales-do — Not sure which skill to use? The router matches any sales objective to the right skill. Install: npx skills add sales-skills/sales --skill sales-do

Examples

Example 1: Building a health score from scratch

User: "I'm a B2B SaaS with 200 customers, $20K ACV. I have no health scoring — where do I start?"

Approach: Start with the 4-metric framework. Pull product usage from Mixpanel/Amplitude (DAU/MAU ratio, key feature adoption), engagement from CRM (email opens, meeting attendance), outcomes from your product (goal completion), and sentiment from NPS surveys. Weight usage at 40%, engagement at 25%, outcomes at 25%, sentiment at 10%. Set initial thresholds: Green > 70, Yellow 40-70, Red < 40. Don't change weights for 6 months. After 6 months, run a retroactive analysis — did Red accounts actually churn? Adjust thresholds based on real data.

Example 2: Churn spiked after a product change

User: "We shipped a major UI redesign last quarter and churn doubled. How do we recover?"

Approach: Segment churn by cohort — are churners concentrated in accounts that relied on the old UI heavily (power users) or across the board? Pull feature usage data pre/post redesign to identify which workflows broke. For active at-risk accounts: send a CSM-led re-onboarding invitation focused on the new workflows. For recently churned: reach out with a "we heard you" campaign offering guided migration + a concession. Long-term: implement a beta program for major changes so power users have transition time.

Example 3: Choosing between Vitally and Gainsight

User: "We're 300 customers, $30K ACV, 5-person CS team. Vitally or Gainsight?"

Approach: At 300 customers and $30K ACV, you're solidly mid-market. Vitally is purpose-built for this — faster setup (2-4 weeks vs 2-6 months for Gainsight), modern UI that CSMs actually enjoy using, and the AI copilot adds immediate value for call prep and summaries. Gainsight has deeper features but most mid-market teams don't use them and end up paying for complexity they don't need. Recommendation: start with Vitally, evaluate Gainsight when you cross 1000+ accounts or need complex org hierarchy support. Request demos from both and evaluate on: time-to-value, CSM adoption (will your team actually use it?), and total cost including implementation.

Troubleshooting

Health scores don't correlate with actual churn

• Retroactive analysis. Pull 12 months of health score data and actual churn events. If Red accounts didn't churn and Green accounts did, your indicators are wrong.
• Check data freshness. If product usage data syncs daily but health scores update weekly, you're always behind. Match cadences.
• Segment your model. Enterprise accounts churn differently than SMB — a single health model may not work across segments.

Onboarding is taking too long

• Map the critical path. Identify the 3-5 steps between "signed contract" and "first value moment." Everything else is optional.
• Identify the bottleneck. Is it data migration? Internal approvals? Training? Technical setup? Each has a different fix.
• Set a time-to-value SLA. "90% of customers reach first value within 14 days." Measure and report on it. What gets measured gets managed.

CS team is reactive, not proactive

• Automate the signal detection. Use a CS platform (Vitally, Gainsight, ChurnZero) to surface at-risk accounts automatically instead of relying on CSMs to check manually.
• Create a daily priority view. Each CSM should start the day with a ranked list of accounts needing attention, ordered by health score and renewal date.
• Ring-fence proactive time. Block 2-3 hours daily for outreach to Yellow/Red accounts. If CSMs are 100% reactive (firefighting), no tool will fix it — it's a capacity problem.