$npx -y skills add ncklrs/startup-os-skills --skill onboarding-specialistExpert customer onboarding guidance for accelerating time-to-value and ensuring successful implementations. Use when designing onboarding programs, creating kickoff frameworks, building implementation plans, or optimizing customer activation. Use for training delivery, go-live re
| 1 | # Onboarding Specialist |
| 2 | |
| 3 | 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. |
| 4 | |
| 5 | ## Philosophy |
| 6 | |
| 7 | Customer onboarding is not a checklist — it's a transformation: |
| 8 | |
| 9 | 1. **Time-to-value is everything** — Every day before value is a day closer to churn |
| 10 | 2. **Onboarding is not training** — It's guiding customers to their specific outcomes |
| 11 | 3. **Structured flexibility** — Framework with personalization, not rigid scripts |
| 12 | 4. **Proactive, not reactive** — Anticipate obstacles before they become blockers |
| 13 | 5. **Handoff is a process** — From sales to CS to ongoing success |
| 14 | |
| 15 | ## How This Skill Works |
| 16 | |
| 17 | When invoked, apply the guidelines in `rules/` organized by: |
| 18 | |
| 19 | - `program-*` — Onboarding program design and kickoff frameworks |
| 20 | - `implementation-*` — Project management and execution |
| 21 | - `training-*` — Enablement and learning delivery |
| 22 | - `handoff-*` — Sales to CS transitions |
| 23 | - `automation-*` — Tech-touch and scaled onboarding |
| 24 | - `signals-*` — Early warning detection and intervention |
| 25 | - `golive-*` — Readiness criteria and launch success |
| 26 | |
| 27 | ## Core Frameworks |
| 28 | |
| 29 | ### The Onboarding Journey |
| 30 | |
| 31 | ``` |
| 32 | ┌─────────────────────────────────────────────────────────────────────────┐ |
| 33 | │ │ |
| 34 | │ HANDOFF → KICKOFF → CONFIGURE → TRAIN → PILOT → GO-LIVE → TRANSITION │ |
| 35 | │ │ |
| 36 | │ ↓ ↓ ↓ ↓ ↓ ↓ ↓ │ |
| 37 | │ Context Alignment Setup Skills Validate Launch Ongoing │ |
| 38 | │ Transfer & Goals & Data & Usage & Iterate Success Success │ |
| 39 | │ │ |
| 40 | └─────────────────────────────────────────────────────────────────────────┘ |
| 41 | ``` |
| 42 | |
| 43 | ### Onboarding Segmentation Model |
| 44 | |
| 45 | | Segment | ARR Range | Touch Model | Duration | Resources | |
| 46 | |---------|-----------|-------------|----------|-----------| |
| 47 | | **Enterprise** | $100K+ | High-touch, dedicated CSM | 90-180 days | Implementation team | |
| 48 | | **Mid-Market** | $25K-$100K | Medium-touch, pooled CSM | 60-90 days | Shared resources | |
| 49 | | **SMB** | $5K-$25K | Low-touch, digital-led | 30-60 days | Scaled programs | |
| 50 | | **Self-Serve** | <$5K | Tech-touch, automated | 14-30 days | In-app + email | |
| 51 | |
| 52 | ### Time-to-Value Framework |
| 53 | |
| 54 | | Milestone | Definition | Target | Measurement | |
| 55 | |-----------|------------|--------|-------------| |
| 56 | | **Time to First Login** | Account created to first access | <24 hours | Login event | |
| 57 | | **Time to Setup** | First login to basic config | <3 days | Config complete | |
| 58 | | **Time to First Value** | Setup to "aha moment" | <7 days | Value event | |
| 59 | | **Time to Full Value** | First value to adoption | <30 days | Usage metrics | |
| 60 | | **Time to Expansion** | Adoption to growth | 60-90 days | Upsell/add users | |
| 61 | |
| 62 | ### The IMPACT Kickoff Framework |
| 63 | |
| 64 | | Phase | Focus | Key Actions | |
| 65 | |-------|-------|-------------| |
| 66 | | **I**ntroductions | People & roles | Stakeholder mapping, team intros | |
| 67 | | **M**utual objectives | Aligned goals | Success criteria definition | |
| 68 | | **P**lan | Timeline & milestones | Project plan creation | |
| 69 | | **A**ccountability | Ownership | RACI establishment | |
| 70 | | **C**ommunication | Rhythm & channels | Meeting cadence, tools | |
| 71 | | **T**imeline | Critical dates | Go-live target, checkpoints | |
| 72 | |
| 73 | ### Customer Health During Onboarding |
| 74 | |
| 75 | | Indicator | Green | Yellow | Red | |
| 76 | |-----------|-------|--------|-----| |
| 77 | | **Engagement** | Active participation | Sporadic responses | No-shows, silence | |
| 78 | | **Progress** | On or ahead of plan | Minor delays | Significantly behind | |
| 79 | | **Adoption** | Using core features | Limited exploration | No usage | |
| 80 | | **Sentiment** | Enthusiastic | Concerned | Frustrated | |
| 81 | | **Champion** | Strong advocate | Neutral | Absent/departed | |
| 82 | |
| 83 | ### Onboarding Metrics |
| 84 | |
| 85 | | Metric | Formula | Benchmark | |
| 86 | |--------|---------|-----------| |
| 87 | | **Time to First Value** | Days from signup to value event | <7 days | |
| 88 | | **Onboarding Completion Rate** | Completed / Started | 85%+ | |
| 89 | | **Time to Go-Live** | Days from kickoff to production | By segment | |
| 90 | | **Onboarding NPS** | Post-onboarding survey | 50+ | |
| 91 | | **90-Day Retention** | Still active at day 90 | 95%+ | |
| 92 | | **Feature Adoption** | Core features used / Available | 60%+ | |
| 93 | | **Onboarding Effort Score** | Customer effort rating | <3 (1-5 scale) | |
| 94 | |
| 95 | ### Risk Categories |
| 96 | |
| 97 | | Category | Signals | Intervention | |
| 98 | |----------|---------|--------------| |
| 99 | | **Technic |