Customer Onboarding Checklist (90-Day)

Field	Value
Type	Skill Resource
Source	`~/.copilot/skills/exec/assets/onboarding_checklist_template.md`
Description	Not specified

Source Content

Customer Onboarding Checklist (90-Day)

Customer: [Customer Name] Segment: [Enterprise / Mid-Market / SMB] CSM: [CSM Name] Kickoff Date: [Date] Target Go-Live: [Date] Target First Value Date: [Date — must be within 30 days]

Phase 1: Welcome and Setup (Days 1-14)

Pre-Kickoff Preparation (Day 0)

Review signed contract and SOW for scope and commitments
Research customer’s industry, business model, and competitive landscape
Review handoff notes from sales team (pain points, decision drivers, stakeholders)
Prepare welcome package (login credentials, documentation links, support contacts)
Create customer workspace in CS platform
Schedule kickoff meeting with all required attendees
Prepare kickoff deck with agenda and success plan draft

Kickoff Meeting (Day 1-2)

Conduct kickoff meeting with customer stakeholders
Confirm business objectives and success criteria
Identify key stakeholders and their roles (sponsor, champion, technical lead, users)
Align on communication cadence and preferred channels
Review onboarding timeline and milestones
Set expectations for time commitment from customer team
Share and agree on success plan (mutual accountability)
Schedule recurring check-in meetings

Kickoff Meeting Notes:

[Document key takeaways, concerns raised, decisions made]

Technical Setup (Days 3-7)

Provision customer environment (tenant, workspace, permissions)
Configure SSO/authentication if applicable
Set up integrations with customer’s existing tools
Import or migrate existing data (if applicable)
Validate data integrity post-migration
Configure role-based access and permissions
Set up monitoring and alerting

Technical Setup Owner: [SE / Implementation team name] Technical Setup Notes:

[Document configuration decisions, customizations, issues]

Admin Training (Days 7-10)

Deliver admin training session (system configuration, user management)
Provide admin documentation and quick reference guide
Ensure admins can independently manage basic operations
Set up admin support escalation path

Initial User Training (Days 10-14)

Deliver core user training (session 1: basic navigation and key workflows)
Provide user quickstart guide and video resources
Set up user support channel (Slack, email, in-app chat)
Confirm all target users have active accounts
Track initial login completion rate

Training Completion Rate: [___%] of target users

Phase 2: Activation (Days 15-30)

User Activation (Days 15-20)

Monitor daily active user metrics
Follow up with users who have not logged in
Conduct follow-up training for users needing additional help
Address any usability issues or confusion reported
Validate that core workflows are functioning as expected
Collect early feedback from champion and key users

Activation Rate: [___%] of licensed users active

First Value Milestone (Days 20-30)

Define and track first value milestone (specific to customer objectives)
Verify customer has completed their first meaningful workflow
Document value delivered (even if small — establish the pattern)
Share “first win” with executive sponsor
Celebrate the milestone with the customer team

First Value Milestone: [Describe the specific milestone] Date Achieved: [Date]

30-Day Review (Day 28-30)

Conduct 30-day review meeting with customer
Review activation metrics (logins, usage, adoption)
Assess progress against success plan milestones
Identify any blockers or concerns
Adjust onboarding plan if needed
Confirm transition from setup phase to adoption phase
Set goals for days 31-60

30-Day Health Score: [Score]/100 — [Green/Yellow/Red]

Phase 3: Adoption (Days 31-60)

Feature Expansion (Days 31-45)

Introduce additional features beyond core workflows
Deliver advanced training session (session 2: power features)
Enable at least one integration with customer’s existing tools
Identify and address feature adoption gaps
Share best practices from similar customers

Usage Benchmarking (Days 45-55)

Compare customer’s usage against segment benchmarks
Identify underperforming areas and create enablement plan
Share usage report with customer champion
Discuss usage targets for the next 30 days

Current vs. Benchmark:

Metric	Current	Benchmark	Gap
Feature Adoption	[%]	[%]	[+/-]
Daily Active Users	[#]	[#]	[+/-]
Key Workflow Completion	[%]	[%]	[+/-]

60-Day Check-in (Day 55-60)

Conduct 60-day check-in meeting
Review adoption metrics and progress
Discuss any roadblocks to deeper adoption
Begin identifying advanced use cases
Set goals for days 61-90

Phase 4: Optimisation (Days 61-90)

Advanced Use Cases (Days 61-75)

Conduct use case discovery workshop with customer
Identify 2-3 advanced use cases beyond initial scope
Build implementation plan for advanced use cases
Begin pilot of advanced use cases with power users

ROI Measurement (Days 75-85)

Collect data for ROI measurement against baseline
Build ROI summary document
Share ROI results with executive sponsor
Document customer testimonial or case study opportunity (if willing)

ROI Summary:

Metric	Baseline	Current	Improvement
[Metric 1]	[Value]	[Value]	[% change]
[Metric 2]	[Value]	[Value]	[% change]

90-Day Executive Review (Days 85-90)

Prepare 90-day executive review presentation
Include: value delivered, adoption metrics, ROI, next steps
Conduct review meeting with executive sponsor
Transition from onboarding to ongoing success management
Establish ongoing success plan with quarterly milestones
Confirm ongoing meeting cadence
Introduce expansion opportunities if appropriate

90-Day Health Score: [Score]/100 — [Green/Yellow/Red]

Onboarding Completion Gate

The following criteria must be met to consider onboarding complete:

User activation rate above 80%
First value milestone achieved within 30 days
Core workflows actively used by target users
Executive sponsor confirms satisfaction
Health score is Yellow (50+) or better
Success plan established with ongoing milestones
Recurring meeting cadence confirmed
Support escalation path understood by customer

Onboarding Status: [Complete / In Progress / Blocked] Completion Date: [Date] Handoff to Steady-State CSM: [Date if different CSM]

Notes

Risks and Blockers

Risk/Blocker	Impact	Mitigation	Status
[Item]	[High/Med/Low]	[Action]	[Open/Resolved]

Key Decisions

Date	Decision	Made By	Impact
[Date]	[Decision]	[Name]	[Description]

Template Version: 1.0 Last Updated: February 2026