# Description
Expert 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 readiness, sales-to-CS handoffs, early warning detection, and tech-touch automation.
# SKILL.md
name: onboarding-specialist
description: Expert 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 readiness, sales-to-CS handoffs, early warning detection, and tech-touch automation.
Onboarding Specialist
Expert guidance for transforming new customers into successful, activated users. The onboarding phase is the most critical window for customer retention β get it right, and you create advocates; get it wrong, and you create churn.
Philosophy
Customer onboarding is not a checklist β it's a transformation:
- Time-to-value is everything β Every day before value is a day closer to churn
- Onboarding is not training β It's guiding customers to their specific outcomes
- Structured flexibility β Framework with personalization, not rigid scripts
- Proactive, not reactive β Anticipate obstacles before they become blockers
- Handoff is a process β From sales to CS to ongoing success
How This Skill Works
When invoked, apply the guidelines in rules/ organized by:
program-* β Onboarding program design and kickoff frameworks
implementation-* β Project management and execution
training-* β Enablement and learning delivery
handoff-* β Sales to CS transitions
automation-* β Tech-touch and scaled onboarding
signals-* β Early warning detection and intervention
golive-* β Readiness criteria and launch success
Core Frameworks
The Onboarding Journey
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β β
β HANDOFF β KICKOFF β CONFIGURE β TRAIN β PILOT β GO-LIVE β TRANSITION β
β β
β β β β β β β β β
β Context Alignment Setup Skills Validate Launch Ongoing β
β Transfer & Goals & Data & Usage & Iterate Success Success β
β β
βββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββββ
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 |
| Introductions |
People & roles |
Stakeholder mapping, team intros |
| Mutual objectives |
Aligned goals |
Success criteria definition |
| Plan |
Timeline & milestones |
Project plan creation |
| Accountability |
Ownership |
RACI establishment |
| Communication |
Rhythm & channels |
Meeting cadence, tools |
| Timeline |
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 β Assumes everyone knows goals
- Feature training without outcomes β Teaching buttons, not value
- No documented success criteria β "Success" becomes subjective
- Single-threaded relationships β One contact = fragile onboarding
- Rigid timelines β No flexibility for customer reality
- Disappearing after go-live β Onboarding is not adoption
- Ignoring early warning signs β Hoping problems resolve themselves
- Same process for all customers β Segment needs differ dramatically
- Delayed value demonstration β All setup, no quick wins
- No post-onboarding handoff β Unclear ongoing ownership