ERP
How do I know what to reorder in Square?
Last updated
Export your item library and your item sales from the Square Dashboard, upload them, and ReorderOwl tells you what to reorder and how much, with a reorder workbook for every item. Today it works in ChatGPT. Claude setup is coming shortly. It is free to start, with nothing to connect in Square. When you ask, it builds the purchase order for you to send to your vendor.
What does ReorderOwl do for Square sellers?
ReorderOwl turns your Square sales and stock counts into a reorder plan. It forecasts each item from your sales history, compares that with the current quantity at each location, and lists what to order, how much, and from which vendor. The assistant shows the most urgent items in the chat, and the workbook covers every item and shows how each number was worked out.
It reads only the files you export. It does not connect to your Square account and does not change anything in it.
Which Square files do I need to export?
| Export | Where in the Square Dashboard | Required? | What it gives ReorderOwl |
|---|---|---|---|
| Item library | Items, then Item library, then Actions, then Export library | Yes | Your items, SKUs, current quantity per location, default vendor and unit cost |
| Item sales (detail) | Reports, then Item sales, then Export | Yes | Every sale, by item, to forecast demand |
| Open purchase orders sheet | Typed from your open orders | Optional | What is already on order, so it is not ordered again |
How do I export each file from Square?
- Item library: in the Square Dashboard, go to Items, then Item library. Click Actions, then Export library, and download the file. It includes the current quantity at each location, the default unit cost and the default vendor name.
- Item sales: go to Reports, then Item sales. Set the date range from the same day 3 years ago (at least 12 months back) to today, all locations. Click Export and choose the detail CSV, one row per sale line.
- Open purchase orders (optional): Square can't export purchase orders, so if you have orders not yet received, type them into a sheet with the columns PO Number, Vendor, SKU, Quantity, Received, Expected Date and Location, and save it as .xlsx or .csv. Skip it if you have none.
- Keep the files as Square names them; don't edit or rename the columns.
Every item variation needs a SKU in Square: variations without one are left out. Fill in each item's default vendor and unit cost too if you can: the purchase orders are grouped by vendor and priced from them.
How do I set it up in ChatGPT?
Create your free ReorderOwl account first and pick Square as your system. Your setup page shows the steps for ChatGPT, with your own connection link. Claude setup is coming shortly.
- In ChatGPT: add ReorderOwl as the setup page shows, attach the two files in a chat with ReorderOwl, and ask something like "What should we reorder this week?"
- Download the reorder workbook and review the most urgent items in the chat.
It always works on your own data; there is no sample mode for Square.
How do purchase orders work with Square?
When you tell the assistant to create a purchase order, ReorderOwl builds it: one order per vendor, with the items, quantities and unit costs. It appears in the chat and on the purchase order sheet of your workbook. You send it to your vendor. ReorderOwl works from your exported files, so nothing is written to Square. On Square for Retail Plus or Premium, you can also enter it under Items, then Purchase orders.
What happens to my Square data?
ReorderOwl keeps a copy of your uploads for your company, holding only the columns it uses. Built workbooks are deleted after 7 days, and each company sees only its own uploads.
Delete account on your account page removes your uploads and workbooks.
Frequently asked questions
Is ReorderOwl free for Square?
Yes, it is free to start. You create an account, export two files from the Square Dashboard, and use it in ChatGPT without any call with us.
Do I need to connect my Square account?
No. ReorderOwl works from the files you export from the Square Dashboard, so there is nothing to connect or authorize.
Can ReorderOwl create purchase orders in Square?
It builds the purchase order for you to send to your vendor. ReorderOwl works from your exported files, so nothing is written to Square.
Do I need Square for Retail?
No. You need item stock counts turned on, so the item library export has the current quantity per location, and your item sales history.
Sources
- Item library spreadsheet glossary, Square Support Center, accessed 2026-10-01
- Create purchase orders, Square Support Center, accessed 2026-10-01