ncklrs

onboarding-specialist

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# Install this skill:
npx skills add ncklrs/startup-os-skills --skill "onboarding-specialist"

Install specific skill from multi-skill repository

# 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 — 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
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 — 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

# Supported AI Coding Agents

This skill is compatible with the SKILL.md standard and works with all major AI coding agents:

Learn more about the SKILL.md standard and how to use these skills with your preferred AI coding agent.