onboarding-plan-builder

name	onboarding-plan-builder
description	Creates a structured customer onboarding plan with phased milestones, success criteria, timeline, and responsibility assignments. Adapts by segment and complexity. Use when asked to build an onboarding plan, structure a customer kickoff, create an implementation timeline, design a go-live plan, or when a new customer needs a clear roadmap from contract signing to value realisation. Also triggers for questions about customer onboarding structure, implementation planning, kickoff preparation, time-to-value planning, or how to set up a new customer for success from day one.
license	MIT
metadata	{"author":"Stephen Rogan","version":"1.0.0","standalone":true}

Onboarding Plan Builder

Creates a phased onboarding plan that gets a new customer from contract signing to measurable value as fast as possible. The onboarding period is the highest-risk and highest-opportunity phase of the customer lifecycle -- the patterns set in the first 90 days predict the next 3 years.

How to Use

Provide:

• Account name, ARR, product tier, segment
• What they bought (which products/modules, how many seats)
• Their goals (why they bought -- what outcomes they expect)
• Implementation complexity (integrations needed, data migration, custom configuration)
• Key contacts (champion, technical lead, executive sponsor, project manager on their side)
• Target go-live date (if committed) or desired timeline
• Any special circumstances (replacing a competitor, seasonal urgency, parallel initiatives)

Onboarding Phases

Phase 1: Kickoff and Planning (Days 1-7)

Objective: Align on goals, timeline, responsibilities, and success criteria before any implementation begins.

Milestone	Deliverable	Owner	Success Criteria
Welcome and introduction	Welcome email sent, CSM introduced, expectations set	CSM	Customer confirms receipt and understanding
Kickoff call	45-60 minute call covering goals, timeline, roles, success criteria	CSM + Customer	Goals and timeline documented and agreed by both sides
Onboarding plan shared	Written plan with milestones, dates, and owners	CSM	Customer approves the plan
Technical requirements gathered	Integration needs, data migration scope, configuration requirements documented	CSM + Technical Lead	All technical prerequisites identified

Kickoff call agenda:

1. Introductions and roles (5 min)
2. Customer goals: what does success look like in 90 days? (10 min)
3. Product overview: what they have access to and how it maps to their goals (10 min)
4. Timeline and milestones: the onboarding roadmap (10 min)
5. Responsibilities: what you will do, what they need to do (5 min)
6. Next steps and questions (5 min)

Phase 2: Technical Setup (Days 7-30)

Objective: Get the product technically ready for use -- integrations live, data migrated, configurations complete.

Milestone	Deliverable	Owner	Success Criteria
Accounts and access provisioned	All users have access with correct permissions	CSM / Ops	All licensed users can log in
Integrations configured	CRM, email, calendar, or other integrations live and syncing	Technical Lead + Customer IT	Data flowing correctly between systems
Data migration complete	Historical data imported and validated	Technical Lead + Customer	Data is accurate and accessible in the product
Configuration complete	Workflows, templates, and settings configured for their use case	CSM + Customer	Configuration matches their stated requirements
Technical validation	Customer confirms the setup is correct and functional	Customer Technical Lead	Sign-off on technical readiness

Phase 3: Adoption and Training (Days 14-60)

Objective: Move from "the product is set up" to "the team is using it."

Milestone	Deliverable	Owner	Success Criteria
Admin training	Product admin(s) trained on configuration and management	CSM / Enablement	Admin can manage settings, users, and configuration independently
End-user training	Core users trained on daily workflows	CSM / Enablement	Users can complete core workflows independently
First workflow completed	Team completes their first real workflow in the product (not a test)	Customer team	Real work is happening in the product
Adoption checkpoint	Usage review at Day 30: who is using it, who is not, what are the barriers	CSM	Adoption rate >50% of licensed users active. Barriers identified for non-adopters

Phase 4: Value Realisation (Days 30-90)

Objective: Demonstrate measurable value from the investment.

Milestone	Deliverable	Owner	Success Criteria
First value metric	Measurable outcome the customer can point to	CSM + Customer	Customer confirms "yes, this is working" with evidence
60-day review	Formal review of adoption, usage, value, and remaining goals	CSM + Customer	Customer satisfied with progress. Gaps identified and addressed
Onboarding close	Transition from onboarding to steady-state management	CSM	All onboarding milestones complete. Success criteria met. Cadence transitions to standard check-in rhythm
90-day assessment	Full assessment: goals achieved, time-to-value, adoption depth, customer satisfaction	CSM	Customer would recommend the onboarding experience. All Phase 1 goals addressed

Segment Adaptations

Segment	Timeline	Complexity	Engagement Level
Enterprise	60-120 days	Multiple integrations, data migration, custom configuration, change management	High: weekly calls, dedicated project management, executive check-ins
Mid-Market	30-60 days	Standard integrations, moderate configuration	Medium: bi-weekly calls, milestone-driven check-ins
SMB	14-30 days	Minimal configuration, self-serve setup	Low: kickoff call, 2-3 check-in emails, adoption checkpoint
PLG / Self-Serve	7-14 days (or fully self-serve)	Zero configuration, in-app guidance	Minimal: automated emails, usage-triggered check-ins, human engagement only if the customer is stuck

Output Format

## Onboarding Plan: [Account Name]
**Start date:** [date] | **Target go-live:** [date]
**ARR:** EUR [amount] | **Segment:** [segment] | **Tier:** [product tier]

### Goals
1. [Customer goal 1 with success metric]
2. [Customer goal 2 with success metric]

### Timeline
| Phase | Dates | Key Milestones |
|-------|-------|---------------|
| Kickoff & Planning | [dates] | Kickoff call, plan agreed |
| Technical Setup | [dates] | Integrations, migration, config |
| Adoption & Training | [dates] | Training complete, first workflow |
| Value Realisation | [dates] | First value metric, onboarding close |

### Responsibilities
| Deliverable | Your Team | Their Team |
|------------|----------|-----------|
| [item] | [who] | [who] |

### Risk Register
| Risk | Mitigation |
|------|-----------|
| [risk] | [plan] |

### Success Criteria
[What "done" looks like for this onboarding]

Common Onboarding Failures

Failure	Root Cause	Prevention
Technical setup stalls	Customer IT team is not prioritising the integration work	Set expectations in kickoff: "We need X from your team by [date]. If this slips, the timeline slips"
Training attendance is low	Users do not see the relevance or their manager did not mandate attendance	Get the champion or executive sponsor to mandate attendance. Frame training as "getting started with the tool that will save your team X hours"
No measurable value by Day 60	Goals were not specific enough to measure	Define measurable success criteria in the kickoff. "You will know onboarding succeeded when [specific metric]"
Champion goes dark during onboarding	They are busy, distracted, or less engaged than expected	Set a weekly cadence. If they miss 2 scheduled touchpoints, escalate to their manager or executive sponsor
Scope creep	Customer wants more configuration, more integrations, more customisation than planned	Scope is defined in Phase 1. Additions are welcome but extend the timeline. Manage expectations explicitly

Quality Gates

• Does every milestone have a success criterion? "Training complete" is not a milestone -- "Users can complete core workflows independently" is
• Are responsibilities assigned to named people? "Their team will handle it" is not an assignment. "[Name] will configure the SSO integration by [date]" is
• Is the timeline realistic? An enterprise onboarding in 14 days is a fantasy. An SMB onboarding that takes 90 days is a failure. Match the timeline to the complexity
• Are the customer's goals captured and measurable? If you cannot measure whether the onboarding achieved its goals, you cannot demonstrate time-to-value -- and time-to-value is the single most important onboarding metric

Principles

• Onboarding is not a project. It is the foundation of the relationship. The speed, quality, and experience of onboarding shape how the customer perceives every interaction that follows. Get it right
• Time-to-value is the metric that matters. Not time-to-go-live, not time-to-training-complete -- time-to-the-first-outcome-the-customer-cares-about. Everything in the plan should compress this number
• The customer's effort determines the timeline, not yours. The most common onboarding delay is waiting for the customer's team to complete their tasks (data migration, integration configuration, internal approvals). Set expectations early and follow up relentlessly
• A customer who finishes onboarding without a measurable value metric is a customer who enters steady-state management with unproven ROI. That makes every subsequent conversation -- especially the renewal -- harder than it needs to be