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:

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:**
| 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):

- Progress review (10 min)

- Blocker resolution (10 min)

- Admin training preview (5 min)

- Next steps (5 min)

Admin Training Agenda (60 min):

- Platform overview (15 min)

- User management (15 min)

- Core workflows (20 min)

- 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):

- Adoption metrics review (10 min)

- Value realization check (10 min)

- Expansion opportunities (5 min)

- 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