Episode 2

Square AI | How Comfortably Chic Is Using Square AI for Retail Inventory Planning

Ryan Hester, owner of the six-location retail store Comfortably Chic, explains how Square AI has transformed the way his team analyzes sales and inventory trends — saving hours of manual work each week.
by Square Nov 25, 2025 — 1 min read

Starring

Starring

Ryan Hester is the owner of Comfortably Chic, a multi-location family owned and operated retail business located in Chester, NJ.

About this video series

Square AI: Better Data for Bolder Business Decisions

Square AI: Better Data for Bolder Business Decisions

Learn how businesses are using Square AI to uncover new insights that help them streamline menus, reduce costs, deepen customer engagement, and more. Get inspired and unlock efficiencies in your own business using the power of AI.
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Transcript

Ryan Hester: When you're dealing with 13,000 different SKUs, it's extremely frustrating trying to boil down to the nitty gritty and seeing what sells.

Square AI has probably already saved me 20 to 30 hours. My name is Ryan Hester, and my family owns six different retail businesses in Chester, New Jersey.

Going from accounting into small business, I knew nothing about having a physical retail storefront. I was very relieved that I had this tool that was built in to the Square suite, that I was able to save my time with.

My family sells a lot of stuff. Soap, lotion, marshmallows, home decor. Square AI has helped me be able to see what some of my best selling items are. Cherry Blossom and jasmine. It's one of our most popular lotions, but it's a bottom worst candle sell, so we moved on and switched it to different scent that’s selling great. Without Square AI, I honestly probably wouldn't have noticed that.

One of the largest things about the fall tourism season is the forecasting of our fall candles. They're all handmade by myself, and my brother-in-law. If we don't make enough, we leave way too many sales on the table. If we make way too much, it's a lot of our own time that's wasted.

With Square AI we were able to ask it to track all of our candle sales over the past four years for our pumpkin spice scent, our apple and cranberry, to figure out the year over year percentage rise, which has helped us figure out truly how much we need to have.

It takes forever for me, exporting the inventory information from Square into Excel or a CSV. With Square AI, I can ask it the direct questions that I want immediately.

One of the ways that I actually was able to start reallocating and reinvesting my time was by opening up a brand new store here a week and a half ago. And I'm excited to go through and start off the new store with it.

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Credits

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Alex Schiff, Product Manager for Square AI, shares how Square AI was developed by working closely with real businesses and how it can unlock valuable insights for you.

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