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