Onboarding Orchestrator

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

Instructions

Step 1: Define Onboarding Phases

Standard 4-Phase Model:

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

Step 4: Define Success Metrics

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:

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:

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:

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

---

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