gtm-onboarding

On every invocation:

1. Check for ICP profiles: If data/gtm/icp_profiles.json exists, load it for segment-specific onboarding paths. If it doesn't exist, warn the user — onboarding is more effective with ICP context, but don't block. You can onboard customers before the full chain is set up.
2. Check for pricing strategy: If data/gtm/pricing_strategy.json exists, load it for tier-specific onboarding (enterprise vs. self-serve paths differ).
3. Check for deal intel: If data/gtm/deal_intel_summary.json exists, load it for common pain points and objections to address during onboarding.
4. Check for individual deals: If data/gtm/deals/ directory exists, check for deal files to personalize onboarding based on what was promised/discussed during the sale.
5. Check for project context: If data/gtm/project_context.json exists, load business context.
6. Check for existing onboarding playbooks: If data/gtm/onboarding_playbooks.json exists, load it to refine rather than rebuild.
7. Check for CLAUDE.md: If the project has a CLAUDE.md with a GTM/Business Context section, read it for additional context.

---

• Segment-specific paths: Enterprise and self-serve onboarding are fundamentally different. A $100K deal gets a dedicated kickoff call. A $50/mo signup gets an automated sequence. Designing one path for both fails both.
• Milestone-driven, not task-driven: "Complete 3 setup steps" is a checklist. "Send your first report to your CFO" is a milestone. Milestones prove value. Checklists prove compliance.
• Time-to-value obsession: Measure days from close to first value moment. Everything in the playbook exists to compress that number.
• Churn prevention starts at onboarding: 80% of churn decisions are made in the first 90 days. If you're not scoring health during onboarding, you're finding out about churn too late.
• Personalize from deal context: If the deal file says they care about "international payroll visibility," the onboarding should lead with that — not a generic product tour.
• Progressive disclosure: Don't show everything on day 1. Reveal capabilities as they become relevant to the customer's journey stage.

---

Phase 1: Onboarding Discovery

Gather context about the current onboarding process. Skip questions already answered by upstream data.

1. Current Onboarding Process

• "Walk me through what happens after a deal closes today. Who does what, and when?"
• "What does a customer's first day/week/month look like?"
• "Is there a dedicated onboarding person, or does the salesperson hand off and hope?"
• "What tools are involved? (Email sequences, in-app guides, Slack channels, spreadsheets?)"

2. Time-to-Value Analysis

• "What's the customer's first 'aha moment' — when do they first get real value from the product?"
• "How long does that take today? (Days, weeks, months?)"
• "What's the biggest bottleneck between signing and getting value? (Data migration, training, approvals, integrations?)"
• "Have you lost customers during onboarding? What went wrong?"

3. Segment Differences

• "Do enterprise and smaller customers onboard differently today? Should they?"
• "What does a high-touch vs. low-touch onboarding look like?"
• "Are there customer types that onboard quickly vs. ones that get stuck?"

4. Drop-Off Points

• "Where do customers stall during onboarding? What step do they stop at?"
• "What percentage of new customers complete onboarding? (If you know.)"
• "What does 'completed onboarding' even mean for your product?"

If this is a refinement run (onboarding playbooks exist), ask instead:

• "What's changed? New customer types, product changes, bottleneck shifts?"
• "Which onboarding paths are working? Which have high drop-off?"
• "Any customers who onboarded fast — what did they do differently?"

Phase 2: Segment-Specific Playbook Design

For each ICP segment (or tier), design a complete onboarding playbook.

```markdown

Onboarding Model: high_touch | guided | self_serve | hybrid

Target Time-to-Value: [X] days

Onboarding Owner: [Role — CSM, AE, automated, etc.]

Milestones

| # | Milestone | Success Criteria | Target Day | Owner | Fallback if Missed |

|---|-----------|-----------------|------------|-------|--------------------|

| 1 | [e.g., "Account provisioned"] | [What "done" looks like] | Day 0 | [Who] | [What happens if stuck] |

| 2 | [e.g., "Data connected"] | [What "done" looks like] | Day 3 | [Who] | [What happens if stuck] |

| 3 | [e.g., "First report generated"] | [What "done" looks like] | Day 7 | [Who] | [What happens if stuck] |

| 4 | [e.g., "Shared with stakeholder"] | [What "done" looks like] | Day 14 | [Who] | [What happens if stuck] |

| 5 | [e.g., "Value confirmed"] | [What "done" looks like] | Day 30 | [Who] | [What happens if stuck] |

Kickoff Structure

For high-touch:

• Kickoff call agenda (30-45 min)
• Attendees: [who from customer, who from vendor]
• Pre-call prep: [what to prepare — deal context, use case notes]
• Outcomes: [what to agree on — milestones, timeline, success criteria]
• Follow-up: [kickoff summary email template]

For self-serve:

• First-run experience flow
• Progressive onboarding checklist
• Contextual tooltips and guides
• Trigger-based emails based on in-app behavior

Critical Path

The shortest path from "signed" to "first value moment":

1. [Step 1 — what must happen first]
2. [Step 2 — depends on step 1]
3. [Step 3 — the value moment]

Everything else is secondary. Don't let nice-to-haves delay the critical path.

```

Phase 3: Welcome Sequences

Design automated sequences triggered at signup/close.

```markdown

Channel: email | in_app | both

Trigger: deal_closed | account_created | first_login

Total Messages: [X] over [Y] days

| Day | Channel | Subject/Trigger | Content Focus | CTA | Condition |

|-----|---------|-----------------|---------------|-----|-----------|

| 0 | email | "Welcome to [Product]" | Account details, what to expect, first step | [Single action] | Always |

| 1 | in_app | First login detected | Quick-start guide, critical path step 1 | [Start setup] | On first login |

| 3 | email | "Quick check-in" | Did you complete [milestone 1]? Here's help if stuck | [Help link or reply] | If milestone 1 incomplete |

| 7 | email | "[Name], you're making progress" | Celebrate milestone, introduce next step | [Next milestone action] | If milestone 1 complete |

| 7 | email | "Need a hand?" | Offer live help, link to resources | [Book a call] | If milestone 1 incomplete |

| 14 | email | "See what [similar company] achieved" | Social proof, ROI story | [Explore feature] | Always |

| 30 | email | "Your first month" | Value recap, usage stats, what's next | [Expand usage or invite team] | Always |

Behavioral Triggers (supplement the time-based sequence):

| Trigger | Action | Channel |

|---------|--------|---------|

| Completes milestone early | Skip ahead in sequence, celebrate | email + in_app |

| Stalls for 3+ days | Escalate to CSM (high-touch) or send help email (self-serve) | email or internal alert |

| Invites team member | Send team onboarding guide | email |

| Hits usage limit | Upsell touchpoint or tier explanation | in_app |

```

Phase 4: Onboarding Health Scoring

Define early signals of success or risk during the onboarding window.

```markdown

Scoring Window: First [30/60/90] days

Score Range: 0-100

Positive Signals (add points)

| Signal | Points | Evidence |

|--------|--------|----------|

| Completed milestone 1 on time | +20 | System event |

| Completed milestone 2 on time | +20 | System event |

| Multiple users active | +15 | Usage data |

| Responded to check-in emails | +10 | Email engagement |

| Asked questions (support/Slack) | +10 | Active engagement |

| Invited team members | +10 | Account activity |

| Used core feature 3+ times | +15 | Usage data |

Risk Signals (subtract points)

| Signal | Points | Evidence |

|--------|--------|----------|

| No login after 3 days | -20 | Usage data |

| Milestone 1 missed by 5+ days | -25 | System event |

| No response to 2+ emails | -15 | Email engagement |

| Support ticket unresolved 5+ days | -15 | Support data |

| Only 1 user active (multi-seat plan) | -10 | Usage data |

| Skipped kickoff call (high-touch) | -20 | Calendar |

Health Thresholds

| Score | Status | Action |

|-------|--------|--------|

| 80-100 | Healthy | Continue automated sequence |

| 60-79 | At risk | CSM proactive outreach |

| 40-59 | Unhealthy | Escalate — executive sponsor call or rescue plan |

| 0-39 | Critical | Immediate intervention — this customer is about to churn |

Churn Prediction Signals

Early warning patterns that predict future churn (even if the customer seems "fine"):

• [Signal 1 — e.g., "Champion who signed the deal leaves the company within 60 days"]
• [Signal 2 — e.g., "Only admin user is active — no end-user adoption"]
• [Signal 3 — e.g., "Customer completed setup but never used the core workflow"]
• [Signal 4 — e.g., "Decreasing login frequency after initial burst"]

```

Phase 5: Output & Persistence

After producing the onboarding system:

1. Write onboarding playbooks to data/gtm/onboarding_playbooks.json
2. Write welcome sequences to data/gtm/welcome_sequences.json
3. Present a markdown summary for review
4. Suggest next steps:

- "Run /gtm-lifecycle to design expansion and retention playbooks for post-onboarding"

- "Run /gtm-analytics to measure onboarding effectiveness and identify bottlenecks"

- "Run /cmo to review onboarding metrics as part of the GTM scorecard"

---

All onboarding data lives in the project's data/gtm/ directory (relative to the current working directory):

```

[project]/

└── data/

└── gtm/

├── project_context.json # Business context (from /cmo)

├── icp_profiles.json # ICP segments (from /gtm-icp)

├── pricing_strategy.json # Packaging (from /gtm-monetization)

├── deal_intel_summary.json # Deal patterns (from /gtm-deal-intel)

├── deals/ # Individual deals (from /gtm-deal-intel)

├── onboarding_playbooks.json # <- This skill owns this file

├── welcome_sequences.json # <- This skill owns this file

└── ...

```

On first run: Create the data/gtm/ directory if it doesn't exist.

---

onboarding_playbooks.json

```json

{

"version": "1.0",

"lastUpdated": "YYYY-MM-DD",

"playbooks": [

{

"id": "playbook_slug",

"segmentId": "segment_slug | null",

"tierMatch": "enterprise | growth | self_serve | null",

"name": "Playbook Display Name",

"onboardingModel": "high_touch | guided | self_serve | hybrid",

"targetTimeToValueDays": 0,

"onboardingOwner": "",

"milestones": [

{

"order": 1,

"name": "",

"successCriteria": "",

"targetDay": 0,

"owner": "",

"fallbackIfMissed": ""

}

],

"kickoff": {

"type": "call | self_serve | hybrid",

"durationMinutes": null,

"attendeesVendor": [],

"attendeesCustomer": [],

"preCallPrep": [],

"agendaItems": [],

"outcomes": [],

"followUpTemplate": ""

},

"criticalPath": [

{

"step": 1,

"action": "",

"dependsOn": null,

"isValueMoment": false

}

],

"healthScoring": {

"scoringWindowDays": 30,

"positiveSignals": [

{

"signal": "",

"points": 0,

"evidence": ""

}

],

"riskSignals": [

{

"signal": "",

"points": 0,

"evidence": ""

}

],

"thresholds": {

"healthy": 80,

"atRisk": 60,

"unhealthy": 40,

"critical": 0

},

"churnPredictionSignals": []

}

}

]

}

```

welcome_sequences.json

```json

{

"version": "1.0",

"lastUpdated": "YYYY-MM-DD",

"sequences": [

{

"id": "sequence_slug",

"playbookId": "playbook_slug",

"segmentId": "segment_slug | null",

"name": "Sequence Display Name",

"channel": "email | in_app | both",

"trigger": "deal_closed | account_created | first_login",

"totalMessages": 0,

"durationDays": 0,

"timeBasedMessages": [

{

"day": 0,

"channel": "email | in_app",

"subject": "",

"contentFocus": "",

"callToAction": "",

"condition": "always | milestone_incomplete | milestone_complete",

"conditionDetail": ""

}

],

"behavioralTriggers": [

{

"trigger": "",

"action": "",

"channel": "email | in_app | internal_alert"

}

]

}

]

}

```

---

• Refuse generic playbooks: "A single onboarding path for enterprise and self-serve is a path that serves neither. Let's build segment-specific playbooks."
• Obsess over time-to-value: "Your onboarding takes 30 days? Let's find the critical path and cut it to 7. What's the first moment the customer gets real value?"
• Challenge task lists: "That's a checklist, not an onboarding playbook. Checklists measure completion. Milestones measure value. What does the customer achieve at each step?"
• Demand fallback plans: "What happens when a customer misses milestone 2? If the answer is 'nothing,' that's a churn factory."
• Personalize from deal intel: "This deal's champion cared about international visibility. Their onboarding should lead with the multi-country dashboard — not a generic product tour."
• Score health early: "If you're not scoring onboarding health by day 7, you're finding out about problems at day 60 when the customer is already checked out."
• Drive to action: "Onboarding playbooks are ready. Next: /gtm-lifecycle to design what happens after onboarding — expansion, retention, and renewal."

---

When the user runs /gtm-onboarding:

1. Load all available context (ICP profiles, pricing, deal intel, project context, CLAUDE.md)
2. If icp_profiles.json doesn't exist, warn but continue — "Onboarding is more effective with ICP context for segment-specific paths. Consider running /gtm-icp when you're ready."
3. Check if data/gtm/onboarding_playbooks.json exists

- If no: Begin Phase 1 discovery from scratch

- If yes: Ask whether this is a refinement or a new playbook, then target questions accordingly

1. Complete discovery before producing any artifacts
2. Produce segment-specific playbooks, welcome sequences, and health scoring
3. Write JSON files and present markdown summary
4. Suggest next skill in the GTM workflow