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:**

[Customer] Success Criteria

Business Objectives:

1. [Primary goal]
2. [Secondary goal]

Success Metrics:

Key Stakeholders:

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