onboarding-specialist

What this skill does

# Onboarding Specialist

Expert guidance for transforming new customers into successful, activated users. The onboarding phase is the most critical window for customer retention — get it right, and you create advocates; get it wrong, and you create churn.

## Philosophy

Customer onboarding is not a checklist — it's a transformation:

1. **Time-to-value is everything** — Every day before value is a day closer to churn
2. **Onboarding is not training** — It's guiding customers to their specific outcomes
3. **Structured flexibility** — Framework with personalization, not rigid scripts
4. **Proactive, not reactive** — Anticipate obstacles before they become blockers
5. **Handoff is a process** — From sales to CS to ongoing success

## How This Skill Works

When invoked, apply the guidelines in `rules/` organized by:

- `program-*` — Onboarding program design and kickoff frameworks
- `implementation-*` — Project management and execution
- `training-*` — Enablement and learning delivery
- `handoff-*` — Sales to CS transitions
- `automation-*` — Tech-touch and scaled onboarding
- `signals-*` — Early warning detection and intervention
- `golive-*` — Readiness criteria and launch success

## Core Frameworks

### The Onboarding Journey

```
┌─────────────────────────────────────────────────────────────────────────┐
│                                                                         │
│  HANDOFF → KICKOFF → CONFIGURE → TRAIN → PILOT → GO-LIVE → TRANSITION  │
│                                                                         │
│     ↓         ↓          ↓         ↓       ↓        ↓          ↓        │
│  Context   Alignment   Setup    Skills   Validate  Launch   Ongoing    │
│  Transfer  & Goals     & Data   & Usage  & Iterate Success  Success    │
│                                                                         │
└─────────────────────────────────────────────────────────────────────────┘
```

### Onboarding Segmentation Model

| Segment | ARR Range | Touch Model | Duration | Resources |
|---------|-----------|-------------|----------|-----------|
| **Enterprise** | $100K+ | High-touch, dedicated CSM | 90-180 days | Implementation team |
| **Mid-Market** | $25K-$100K | Medium-touch, pooled CSM | 60-90 days | Shared resources |
| **SMB** | $5K-$25K | Low-touch, digital-led | 30-60 days | Scaled programs |
| **Self-Serve** | <$5K | Tech-touch, automated | 14-30 days | In-app + email |

### Time-to-Value Framework

| Milestone | Definition | Target | Measurement |
|-----------|------------|--------|-------------|
| **Time to First Login** | Account created to first access | <24 hours | Login event |
| **Time to Setup** | First login to basic config | <3 days | Config complete |
| **Time to First Value** | Setup to "aha moment" | <7 days | Value event |
| **Time to Full Value** | First value to adoption | <30 days | Usage metrics |
| **Time to Expansion** | Adoption to growth | 60-90 days | Upsell/add users |

### The IMPACT Kickoff Framework

| Phase | Focus | Key Actions |
|-------|-------|-------------|
| **I**ntroductions | People & roles | Stakeholder mapping, team intros |
| **M**utual objectives | Aligned goals | Success criteria definition |
| **P**lan | Timeline & milestones | Project plan creation |
| **A**ccountability | Ownership | RACI establishment |
| **C**ommunication | Rhythm & channels | Meeting cadence, tools |
| **T**imeline | Critical dates | Go-live target, checkpoints |

### Customer Health During Onboarding

| Indicator | Green | Yellow | Red |
|-----------|-------|--------|-----|
| **Engagement** | Active participation | Sporadic responses | No-shows, silence |
| **Progress** | On or ahead of plan | Minor delays | Significantly behind |
| **Adoption** | Using core features | Limited exploration | No usage |
| **Sentiment** | Enthusiastic | Concerned | Frustrated |
| **Champion** | Strong advocate | Neutral | Absent/departed |

### Onboarding Metrics

| Metric | Formula | Benchmark |
|--------|---------|-----------|
| **Time to First Value** | Days from signup to value event | <7 days |
| **Onboarding Completion Rate** | Completed / Started | 85%+ |
| **Time to Go-Live** | Days from kickoff to production | By segment |
| **Onboarding NPS** | Post-onboarding survey | 50+ |
| **90-Day Retention** | Still active at day 90 | 95%+ |
| **Feature Adoption** | Core features used / Available | 60%+ |
| **Onboarding Effort Score** | Customer effort rating | <3 (1-5 scale) |

### Risk Categories

| Category | Signals | Intervention |
|----------|---------|--------------|
| **Technical** | Integration failures, data issues | Technical escalation |
| **Adoption** | Low usage, training gaps | Additional enablement |
| **Champion** | Key person absent or leaving | Relationship building |
| **Timeline** | Missed milestones, delays | Replan and resource |
| **Scope** | Expanding requirements | Change management |
| **Political** | Internal resistance | Executive alignment |

## Onboarding Project Phases

### Phase 1: Pre-Kickoff (Days -7 to 0)

| Activity | Owner | Deliverable |
|----------|-------|-------------|
| Sales handoff call | AE + CSM | Handoff document |
| Account research | CSM | Company brief |
| Success criteria draft | CSM | Draft goals |
| Kickoff prep | CSM | Agenda, materials |
| Technical assessment | SE/CSM | Readiness checklist |

### Phase 2: Kickoff (Day 1)

| Activity | Duration | Participants |
|----------|----------|--------------|
| Introductions | 10 min | All stakeholders |
| Goals alignment | 20 min | Decision makers |
| Success criteria | 20 min | All |
| Project plan review | 15 min | Project leads |
| Q&A | 15 min | All |
| Next steps | 10 min | All |

### Phase 3: Configuration (Days 2-14)

| Activity | Owner | Dependency |
|----------|-------|------------|
| Instance setup | Vendor | Kickoff complete |
| Data migration | Joint | Data prep complete |
| Integration config | Technical | API access |
| User provisioning | Customer | User list |
| Custom settings | Joint | Requirements |

### Phase 4: Training (Days 15-30)

| Audience | Format | Content |
|----------|--------|---------|
| Admins | Live workshop | Full platform training |
| Power users | Live + self-paced | Core workflows |
| End users | Self-paced + guides | Daily usage |
| Executives | Brief overview | Dashboards, value |

### Phase 5: Pilot & Go-Live (Days 30-45)

| Milestone | Criteria | Validation |
|-----------|----------|------------|
| Pilot ready | Core config complete | Checklist sign-off |
| Pilot launch | Test group identified | User feedback |
| Pilot success | Criteria met | Metrics review |
| Go-live ready | All criteria met | Readiness checklist |
| Go-live | Full rollout | Launch communication |

## Anti-Patterns

- **Skipping kickoff alignment** — Assumes everyone knows goals
- **Feature training without outcomes** — Teaching buttons, not value
- **No documented success criteria** — "Success" becomes subjective
- **Single-threaded relationships** — One contact = fragile onboarding
- **Rigid timelines** — No flexibility for customer reality
- **Disappearing after go-live** — Onboarding is not adoption
- **Ignoring early warning signs** — Hoping problems resolve themselves
- **Same process for all customers** — Segment needs differ dramatically
- **Delayed value demonstration** — All setup, no quick wins
- **No post-onboarding handoff** — Unclear ongoing ownership