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Ask your POS AI what's selling instead of exporting spreadsheets
Ryan Hester, owner of Comfortably Chic, a family business with six retail shops in Chester, NJ (Square video)
He asks Square AI direct questions, such as four years of pumpkin-spice and apple-cranberry candle sales with the year-over-year change, to decide how much to order.
See the vendor’s pricing
Easy · or we do it from $497
Square
The problem
With 13,000 SKUs, working out what sells meant exporting inventory from Square into Excel.
What happened
Self-reported in Square's video: about 20 to 30 hours saved, time he put into opening a new store.
Vendor case study Quoted in the source: Ryan Hester, owner, Comfortably Chic. Source: Square video (2025-11-25) · Added 2026-10-13. Results as reported by the source; we haven't independently verified them.
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How to set it up yourself
- Start with one buying decision you make every season.
- Ask for multi-year sales of those items.
- Check one answer against a manual export.
- Use the trend to set reorder quantities.
Copy-paste prompt
Show sales of {ITEM GROUP} by month for the last {N} years with year-over-year % change, then suggest an order quantity for {SEASON} with your reasoning.Tools used
Square
Point of sale and payments with AI assistant features.
From $0 (free plan; processing fees apply) (checked 2026-10-13)
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Checked prices: Square: from $0 (free plan; processing fees apply) (verified 2026-10-13)
Rather not do it yourself?
We'll set this up in your tools, in your voice, tested. Single use case $497. Satisfaction guarantee: we'll fix it until it works, or refund your setup fee. Terms. We reply within 1 business day.
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