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

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

What Claude Does vs What You Decide

Instructions

Step 1: Define Onboarding Phases

Step 2: Map Milestones per Phase

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

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

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

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

Step 3: Design Touchpoint Cadence

Step 4: Define Success Metrics

Examples

Example 1: B2B SaaS Onboarding Playbook

## 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:**
-

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

Phase 2: Setup (Days 8-21)

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

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

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

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

Phase 3: Adoption (Days 22-45)

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

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

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

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)

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

Phase 4: Optimization (Days 46-90)

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

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

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

Automation Triggers

Risk Indicators

## 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