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Customer segment onboarding timeline builder

Generates a phased onboarding project timeline calibrated to customer segment (SMB, Mid-Market, or Enterprise) with milestone dates, task owners, Time-to-Value checkpoints, risk flags, and a customer-facing summary…

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Purpose

Produce a phased, date-stamped onboarding timeline tuned to a specific customer segment and reverse-engineered from a target activation date — with named phases, milestone gates, owner assignments, and Time-to-Value checkpoints — so implementations stay on schedule and customers reach first value within segment benchmarks instead of drifting.

When to Use

Invoke this skill when the user asks to:

  • Build an onboarding or implementation timeline for a new customer
  • Plan a project schedule to hit a specific go-live or activation date
  • Standardize onboarding plans across SMB, Mid-Market, and Enterprise segments
  • Estimate how long onboarding should take and when first value lands
  • Create a phased kickoff-to-activation plan with owners and milestones
  • Turn a signed contract or target launch date into a working project plan

Inputs Required

Before starting, collect:

  • Customer segment: SMB / Mid-Market (MM) / Enterprise (ENT)
  • Target activation date: The date the customer must be live or reaching first value
  • Kickoff or start date: When onboarding begins (defaults to today if omitted)
  • Product complexity: Self-serve setup / Guided config / Custom integration & migration
  • Key deliverables or integrations: Data migration, SSO, API integrations, custom training, etc.
  • Team resources: Who is available (CSM, Implementation Manager, Solutions Engineer, Support)
  • Known constraints: Customer-side blockers, holidays, freeze windows, hard deadlines

If complexity or resources are missing, apply segment defaults (SMB: self-serve, single owner; MM: guided, CSM + IM; ENT: custom, full pod) and note the assumption.

Instructions

Step 1: Establish Segment Baseline and Time-to-Value Benchmark

Anchor the plan to segment norms before scheduling anything.

Time-to-Value (TTV) benchmarks by segment:

  • SMB: First value in 7–14 days; full activation in 14–30 days. Low-touch, template-driven.
  • Mid-Market: First value in 21–45 days; full activation in 45–90 days. Guided, moderate integration.
  • Enterprise: First value in 45–90 days; full activation in 90–180 days. High-touch, custom integration and change management.

State the benchmark TTV window for the selected segment and flag immediately if the target activation date is inside or outside that window.

Step 2: Reverse-Engineer the Timeline

Work backward from the target activation date, not forward from kickoff.

  • Anchor the Go-Live / Activation milestone on the target date
  • Subtract each phase duration to place preceding milestones
  • If the resulting start date is later than the provided kickoff, note the slack
  • If it is earlier than the kickoff (impossible), flag the timeline as at risk and recommend either scope reduction or a revised activation date

Step 3: Build the Phase Structure

Use these phases, adjusting duration by segment:

Phase 1 — Kickoff & Alignment

  • Kickoff call, success criteria definition, stakeholder map, project plan sign-off
  • SMB: 1–2 days · MM: 3–5 days · ENT: 5–10 days

Phase 2 — Discovery & Requirements

  • Data audit, integration scoping, technical requirements, access provisioning
  • SMB: 1–3 days · MM: 5–10 days · ENT: 10–20 days

Phase 3 — Configuration & Setup

  • Account config, workspace setup, roles/permissions, branding
  • SMB: 2–4 days · MM: 7–14 days · ENT: 15–30 days

Phase 4 — Integration & Data Migration

  • SSO, API connections, data import, validation (skip or compress if none)
  • SMB: 0–2 days · MM: 5–15 days · ENT: 15–45 days

Phase 5 — First-Value Milestone (TTV Checkpoint)

  • The customer completes their first meaningful action / sees first outcome
  • This is a hard gate — do not advance until confirmed

Phase 6 — Training & Enablement

  • Admin training, end-user training, documentation handoff, certification (ENT)
  • SMB: 1 day · MM: 3–7 days · ENT: 10–20 days

Phase 7 — Go-Live / Activation

  • Full rollout, launch confirmation, success criteria validation

Phase 8 — Post-Activation & Handoff

  • 30/60/90 check-ins, handoff to CSM, adoption review
  • Runs 30–90 days beyond activation depending on segment

Step 4: Assign Owners and Milestone Gates

For each phase, assign:

  • Owner: The single accountable role
  • Customer-side dependency: What the customer must provide, and by when
  • Milestone gate: The binary condition that must be true to advance (e.g., "Data validated: yes/no")

Step 5: Flag Risks and Buffers

  • Mark any phase where duration is compressed below segment minimum as schedule risk
  • Add a buffer of 10–15% of total duration before Go-Live for MM and ENT
  • Flag customer-side dependencies as the top delay driver and note mitigation
  • Call out any conflict between the target date and TTV benchmark explicitly

Step 6: Produce the Customer-Facing Summary

Condense the internal plan into a clean, 3–5 milestone summary the customer can read — phases, dates, and what's expected from them — without internal owner or risk detail.

Output Format

  • Structure: Segment baseline callout → reverse-engineered timeline table → phase-by-phase breakdown → risk flags → customer-facing summary
  • Length: 800–1,200 words
  • Format: Timeline as a table (Phase / Start Date / End Date / Duration / Owner / Gate); phase detail as structured bullets; customer summary as a short milestone list
  • Sections: TTV Benchmark & Feasibility → Master Timeline Table → Phase Breakdown with Owners & Gates → Risk Flags & Buffers → Customer-Facing Summary
  • Tone: Implementations project lead — precise, date-driven, accountability-first

Quality Checklist

Before delivering output, verify:

  • [ ] The timeline is reverse-engineered from the target activation date, with dated milestones
  • [ ] The selected segment's TTV benchmark is stated and feasibility against the target date is judged (on track / at risk)
  • [ ] All 8 phases are present with segment-appropriate durations
  • [ ] Every phase has a single named owner and a binary milestone gate
  • [ ] The First-Value (TTV) checkpoint is placed as an explicit gated milestone
  • [ ] A customer-facing summary is included and contains no internal owner or risk detail

Notes

  • Customer-side dependencies are the number one cause of onboarding slip — surface them early with hard due dates
  • If the target activation date is impossible for the segment, say so plainly and offer two options: reduce scope (defer integrations to post-activation) or move the date
  • For ENT deals, treat the First-Value milestone as separate from Go-Live — proving value before full rollout de-risks the account
  • Duplicating this timeline as a reusable template per segment is the fastest path to standardized onboarding

How to use this skill

This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.

Installing in Claude Code:

  • ~/.claude/skills/<folder-name>/SKILL.md — auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)
  • <your-project>/.claude/skills/<folder-name>/SKILL.md — auto-loads only when working in that project (recommended for project-specific skills)

Restart Claude Code or open a new session to register.

Using in Claude.ai, ChatGPT, Gemini, or other AI tools:

  1. Drag this file into a new chat, or copy and paste its contents
  2. Send your task or request as your next message — the AI will apply the skill where it fits

For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills