Customer Success pack
Claude Skill

Onboarding Playbook Builder

Designs a customer onboarding playbook that gets customers to first value fast — without consuming the CS team's entire week.

What it does

Builds a structured onboarding plan: week-by-week milestones, owner per milestone, customer-facing artifacts, internal handoff checklist. Designed to scale beyond white-glove without sacrificing activation.

When to use

  • New customer segment requires a new onboarding flow
  • Existing onboarding is producing poor activation (customers ghost in week 2)
  • CS team is drowning in onboardings and need a repeatable playbook

When not to use

  • You have < 10 customers — over-engineering before the pattern is clear
  • Your onboarding is genuinely white-glove because every customer is different (rare)

Install

Download the .zip, then unzip into your Claude skills folder.

mkdir -p ~/.claude/skills
unzip ~/Downloads/onboarding-playbook-builder.zip -d ~/.claude/skills/

# Restart Claude Code session.
# Skill is now available — Claude will use it when relevant.

SKILL.md

SKILL.md
---
name: onboarding-playbook-builder
description: Use when designing or redesigning a customer onboarding playbook. Triggers on "onboarding playbook", "customer activation", "first value", "implementation plan".
---

# Onboarding Playbook Builder

Onboarding done well lifts retention by 20-40%. Done badly, it's the source of half your future churn. The playbook converts CS effort from "white glove every customer" to "consistent value delivery at scale."

## Required inputs

1. **Customer segment** — SMB / mid-market / enterprise; ACV range; vertical
2. **The "first value" definition** — what should the customer be able to do or see in their first N days
3. **Stakeholders involved** — champion, admin, end users, exec sponsor
4. **Typical implementation complexity** — pure SaaS signup vs. integration / SSO / data migration
5. **Current onboarding pain points** — what's breaking now (if redesigning)

## Output

### Phase model (typically 4 phases)
- **Phase 1: Kickoff (week 1)** — alignment, expectations, success criteria
- **Phase 2: Foundation (week 1-2)** — setup, integrations, admin training
- **Phase 3: Activation (week 2-4)** — first real use, first value, end-user adoption
- **Phase 4: Adoption (week 4-8)** — usage habits, expansion, internal champion

### Per-phase plan
| Phase | Milestones | Owner (us / customer) | Artifact | Risk if missed |
|---|---|---|---|---|

### Customer-facing artifacts
- Welcome email + first-week schedule
- Kickoff agenda template (60 min, structured)
- Implementation checklist (clear who-does-what)
- Quick-win playbook (the 3 things to do in week 1 that prove value)
- 30/60/90 day check-in agendas

### Internal handoff
- Sales → CS: what info CS needs from the closed deal (not just contract — context, expectations, concerns)
- CS → Support after activation: what's "done" looks like

### Activation milestones (measurable)
The specific things you'll watch:
- Admin logged in within X days
- N users invited within X days
- First key action taken within X days
- Champion has run a team training within X days

### Red flags during onboarding
- Customer ghosting kickoff
- Admin not engaging in week 1
- "We'll start using it next month" stalls
- Internal champion handoff to someone new

For each: the specific intervention.

### Where the playbook breaks down
Honest. The customer segments / situations where the standard playbook won't work and needs adaptation.

## Anti-patterns
- Hour-by-hour rigid plan (real customers have real schedules)
- "We'll figure it out" handoff from sales (predictable disaster)
- Skipping the success-criteria conversation in kickoff
- Treating onboarding as "training" rather than "getting to value"

## Cadence + ownership
- Per-customer: weekly status email through phase 1-3, then check-in cadence
- Per-CSM: portfolio review of all onboardings monthly
- Team: quarterly retro on which segments are activating well, which aren't

Example prompts

Once installed, try these prompts in Claude:

  • Design an onboarding playbook for mid-market B2B SaaS customers (ACV $30-60K). First value should land in 14 days.
  • Our enterprise onboarding takes 90 days and the team is burnt out. Help me redesign for repeatability.