Onboarding Orchestrator

Create structured onboarding programs that drive rapid time-to-value through milestone-based playbooks, proactive touchpoints, and early success metrics.

When to Use This Skill

• Designing new onboarding programs
• Improving existing onboarding metrics
• Creating segment-specific playbooks
• Automating onboarding touchpoints
• Measuring onboarding effectiveness

Methodology Foundation

Based on Lincoln Murphy's First Value Delivery and Gainsight Onboarding Best Practices, focusing on:

• Time to First Value (TTFV)
• Milestone-based progression
• Success criteria definition
• Risk identification during ramp

What Claude Does vs What You Decide

| Claude Does | You Decide | |-------------|------------| | Designs milestone frameworks | Implementation timeline | | Creates touchpoint schedules | Resource allocation | | Identifies success metrics | Definition of "success" | | Suggests automation triggers | Tool selection | | Builds playbook templates | Customization per segment |

Instructions

Step 1: Define Onboarding Phases

Standard 4-Phase Model:

| Phase | Duration | Focus | Exit Criteria | |-------|----------|-------|---------------| | Kickoff | Week 1 | Alignment, access | Kickoff complete, logins work | | Setup | Week 2-3 | Configuration | Core setup done | | Adoption | Week 4-6 | First use case | TTFV achieved | | Optimization | Week 7-12 | Full rollout | Steady state reached |

Step 2: Map Milestones per Phase

Kickoff Milestones:

• [ ] Kickoff call completed
• [ ] Success criteria documented
• [ ] Admin account created
• [ ] Integration requirements identified
• [ ] Timeline agreed

Setup Milestones:

• [ ] Technical setup complete
• [ ] Data migration (if needed)
• [ ] Integrations connected
• [ ] User accounts provisioned
• [ ] Admin trained

Adoption Milestones:

• [ ] First workflow created
• [ ] 50% users logged in
• [ ] First value moment achieved
• [ ] End user training complete
• [ ] Champion identified

Optimization Milestones:

• [ ] 80% users active
• [ ] Full use case deployed
• [ ] Self-service adoption
• [ ] QBR scheduled
• [ ] Expansion discussed

Step 3: Design Touchpoint Cadence

| Day | Type | Purpose | Owner | |-----|------|---------|-------| | 0 | Email | Welcome + next steps | Auto | | 1 | Call | Kickoff call | CSM | | 3 | Email | Setup checklist | Auto | | 7 | Call | Setup review | CSM | | 14 | Email | Training resources | Auto | | 21 | Call | Adoption check-in | CSM | | 30 | Email | 30-day survey | Auto | | 45 | Call | Value review | CSM | | 60 | Email | Optimization tips | Auto | | 90 | Call | QBR/Health check | CSM |

Step 4: Define Success Metrics

| Metric | Target | Measurement | |--------|--------|-------------| | Time to Kickoff | <3 days | Contract → Kickoff | | Time to Setup | <14 days | Kickoff → Setup complete | | Time to First Value | <30 days | Contract → First use case | | 30-day activation | >70% | Users logged in | | 60-day adoption | >50% | Users weekly active | | Onboarding CSAT | >4.5 | Survey score | | Onboarding NPS | >50 | Survey score |

Examples

Example 1: B2B SaaS Onboarding Playbook

Output:

## Customer Onboarding Playbook: Enterprise Segment

### Overview
- **Segment**: Enterprise ($100K+ ARR)
- **Target TTFV**: 45 days
- **CSM:Account Ratio**: 1:15
- **Onboarding Duration**: 90 days

---

### Phase 1: Kickoff (Days 0-7)

**Objectives:**
- Establish relationship and trust
- Align on success criteria
- Set expectations and timeline

**Milestones:**
| Milestone | Owner | Day | Status |
|-----------|-------|-----|--------|
| Welcome email sent | Auto | 0 | |
| Kickoff scheduled | CSM | 1 | |
| Kickoff call completed | CSM | 3 | |
| Success criteria doc sent | CSM | 4 | |
| Technical requirements gathered | CSM | 5 | |
| Project plan shared | CSM | 7 | |

**Kickoff Call Agenda (60 min):**
1. Introductions (5 min)
2. Business objectives (15 min)
3. Success criteria definition (15 min)
4. Technical overview (10 min)
5. Timeline and milestones (10 min)
6. Q&A and next steps (5 min)

**Success Criteria Template:**
```markdown
## [Customer] Success Criteria

**Business Objectives:**
1. [Primary goal]
2. [Secondary goal]

**Success Metrics:**
| Metric | Baseline | Target | Timeline |
|--------|----------|--------|----------|
| [Metric 1] | X | Y | 90 days |

**Key Stakeholders:**
| Name | Role | Involvement |
|------|------|-------------|

**Risks/Dependencies:**
-

Exit Criteria → Phase 2:

• [ ] Kickoff call complete
• [ ] Success criteria documented and signed off
• [ ] Technical requirements understood
• [ ] Project timeline agreed

---

Phase 2: Setup (Days 8-21)

Objectives:

• Complete technical implementation
• Configure product for use case
• Provision and train admins

Milestones: | Milestone | Owner | Day | Status | |-----------|-------|-----|--------| | SSO/Auth configured | Tech | 10 | | | Core integration connected | Tech | 12 | | | Data migration complete | Tech | 14 | | | Admin accounts created | CSM | 14 | | | Admin training session | CSM | 16 | | | Setup review call | CSM | 21 | |

Setup Check-In Call (Day 14, 30 min):

1. Progress review (10 min)
2. Blocker resolution (10 min)
3. Admin training preview (5 min)
4. Next steps (5 min)

Admin Training Agenda (60 min):

1. Platform overview (15 min)
2. User management (15 min)
3. Core workflows (20 min)
4. Reporting basics (10 min)

Exit Criteria → Phase 3:

• [ ] Technical setup 100% complete
• [ ] At least 1 admin trained
• [ ] Users provisioned
• [ ] No open blockers

---

Phase 3: Adoption (Days 22-45)

Objectives:

• Achieve first value moment
• Drive user adoption
• Establish usage patterns

Milestones: | Milestone | Owner | Day | Status | |-----------|-------|-----|--------| | End user training scheduled | CSM | 22 | | | First training session | CSM | 25 | | | First workflow live | Customer | 28 | | | 50% users logged in | - | 30 | | | First value achieved | - | 35 | | | Adoption review call | CSM | 45 | |

End User Training (60 min per session):

• Session 1: Core functionality
• Session 2: Advanced features
• Session 3: Best practices

First Value Checklist:

• [ ] Primary use case configured
• [ ] First real work completed
• [ ] Customer confirms value
• [ ] Quote-worthy moment captured

30-Day Survey:

1. How easy was onboarding? (1-5)
2. Did you achieve your first goal? (Y/N)
3. What could we improve?
4. NPS: How likely to recommend? (0-10)

Exit Criteria → Phase 4:

• [ ] First value moment achieved
• [ ] 50%+ users logged in
• [ ] No critical blockers
• [ ] Customer confirms progress

---

Phase 4: Optimization (Days 46-90)

Objectives:

• Full use case deployment
• Drive to steady-state adoption
• Prepare for ongoing success

Milestones: | Milestone | Owner | Day | Status | |-----------|-------|-----|--------| | Second use case identified | CSM | 50 | | | Full team rollout | Customer | 60 | | | 80% adoption achieved | - | 75 | | | QBR scheduled | CSM | 80 | | | Handoff to ongoing success | CSM | 90 | |

60-Day Check-In (30 min):

1. Adoption metrics review (10 min)
2. Value realization check (10 min)
3. Expansion opportunities (5 min)
4. Ongoing cadence (5 min)

90-Day QBR Handoff:

• Full value review
• Health score baseline
• Ongoing success plan
• Expansion discussion

---

Automation Triggers

| Trigger | Action | Timing | |---------|--------|--------| | Contract signed | Welcome email | Immediate | | Day 3, no kickoff | Alert CSM | Day 3 | | Setup incomplete | Nudge email | Day 18 | | Day 30, <25% login | Risk alert | Day 30 | | First value achieved | Celebration email | On event | | Day 45, low adoption | Intervention call | Day 45 |

---

Risk Indicators

| Signal | Risk Level | Response | |--------|------------|----------| | No kickoff by Day 5 | 🟠 High | Escalate internally | | Setup blocked >7 days | 🟠 High | Technical escalation | | <25% login at Day 30 | 🔴 Critical | Intervention call | | Champion disengaged | 🟠 High | Find alternate contact | | No first value by Day 45 | 🔴 Critical | Executive involvement |

## Skill Boundaries

### What This Skill Does Well
- Structuring onboarding programs
- Defining milestones and metrics
- Creating touchpoint schedules
- Building playbook templates

### What This Skill Cannot Do
- Know your specific product setup
- Execute onboarding automatically
- Replace customer relationship skills
- Predict implementation blockers

### When to Escalate to Human
- Technical implementation issues
- Customer relationship problems
- Scope changes or delays
- Executive involvement needs

## References

- Lincoln Murphy's Customer Success Onboarding
- Gainsight Onboarding Best Practices
- Totango Time to First Value Guide
- ChurnZero Onboarding Automation

## Related Skills

- `account-health` - Post-onboarding health
- `churn-prediction` - Onboarding risk signals
- `expansion-signals` - Early expansion opportunities

## Skill Metadata

- **Domain**: Customer Success
- **Complexity**: Intermediate
- **Mode**: cyborg
- **Time to Value**: 2-4 hours for playbook design
- **Prerequisites**: Product knowledge, segment definitions