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Playbook

The POS migration playbook

A 5 week field tested plan to move a chain from legacy POS to an AI native operator layer without losing a Saturday.

  • POS strategy
  • Operations
  • Multi store

Why this playbook exists

Most POS migrations break down for the same reason: the project plan was written by someone who has never run a Saturday at peak. This playbook is the opposite. It is written from the floor up.

Five weeks. Five phases. The plan you can put in front of a CFO, a CTO, and a store manager and have all three sign off without a war.

What is inside

Phase 1. The truth audit (week 1) The 18 questions every retailer should answer before they look at vendors. Where the data actually lives. Where the workflow actually breaks. Where you are losing margin without knowing it.

Phase 2. The vendor short list (week 2) The 9 vendor questions that matter and the 22 that do not. How to read a demo. How to read a contract. How to test latency in store, not in a slide.

Phase 3. The pilot store (week 3) Choosing the right pilot, not the easy one. The success metrics that matter. The fallback plan for the day it goes wrong.

Phase 4. The rollout (week 4) The cluster strategy. The training that actually sticks. The day one runbook. The first Saturday checklist.

Phase 5. The cutover (week 5) The 72 hour cutover window. The hand back from project to operations. The thirty day post mortem template.

Who this is for

Retail leaders running between 5 and 200 stores who have outgrown a transactional POS and want a system that runs the operation, not just the till. Project leads, CTOs, ops directors, and the store managers who will live with whatever you choose.

What you get

A field tested plan you can adapt to your chain in an afternoon. Checklists you can hand to a store manager. A vendor scorecard you can run through in 90 minutes. A sample 72 hour cutover schedule.

This is the document we wished existed when we started Karo. So we wrote it.

Get the playbook

Drop your email and we will send the full playbook plus the field checklists.

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