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:**[Customer] Success Criteria
Business Objectives:
- [Primary goal]
- [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:**- How easy was onboarding? (1-5)
- Did you achieve your first goal? (Y/N)
- What could we improve?
- 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