Square AI Stopped Me From Drowning in Spreadsheets and Helped Me Open My Sixth Store

Square AI Stopped Me From Drowning in Spreadsheets and Helped Me Open My Sixth Store
How a former corporate accountant helped grow the family’s retail business to six locations by using Square AI to quickly analyze sales, inventory, seasonality, and customer behavior.
by Ryan Hester Jan 07, 2026 — 4 min read
Square AI Stopped Me From Drowning in Spreadsheets and Helped Me Open My Sixth Store

I made a pretty crazy move in 2020 when I left my corporate accounting job in San Francisco to join my family’s retail business, Comfortably Chic, on the other side of the country in Chester, New Jersey. I was ready to apply everything I learned in the corporate world to help my family business grow and thrive. It’s already paying off. We just opened up our sixth location, and our family is managing more than 13,000 SKUs across cooking supplies, home goods, handmade soaps and candles. It’s very exciting, but it’s also incredibly complex. It didn’t take me long to learn that data is everything.

Typically, I want to know which items are flying off the shelves, which ones are collecting dust, and how foot traffic looks compared to the same time last week or the same date a year ago. I’d pull reports from Square, which were impressive and robust, but I’d spend hours working through all of the data in Excel.

When AI tools became more accessible, I got a little creative. I started importing my Square data into ChatGPT, prompting it to aggregate and visualize the numbers. And while it was better, it wasn’t ideal. I was still moving data around, trying to craft ideal prompts and troubleshooting when it wasn’t working the way I wanted it to.

Everything changed when the Square AI symbol popped up on my dashboard. Square AI immediately improved my day-to-day. Now I can ask questions about my specific business data and get quick and accurate answers.

I’m not kidding when I say Square AI has saved me 30 hours of work since I started using it over the summer, and once our busy season wraps up, it probably will have saved me about 200 hours.

Here’s what I’ve learned since I started using it.

Lesson 1: Uncover insights that drive smart stocking decisions

There are so many ways to digest and use our business data, especially with six different locations and thousands of products. We’re always looking to make smarter merchandising, stocking and purchasing decisions, so we can experiment and learn buyer behavior quickly.

We want to know what’s selling and what isn’t, and boiling down the numbers accurately can get frustrating. But Square AI lets me immediately and directly ask the questions I want answers to. Now I’m easily able to identify top sellers we want to double down on, low performers that aren’t worth restocking and trends that are hard to spot quickly.

Here’s a perfect example: When it comes to our soaps and lotions, Cherry Blossom & Jasmine is a top-performing scent. But it’s not a high-performing candle scent. If we didn’t have Square AI to help us uncover that insight, I would have never noticed. We swapped out the Cherry Blossom & Jasmine scent for a different candle scent that’s a higher performer.

These little discoveries quickly add up and improve the business.

Lesson 2: Use historical data to forecast seasonal demand

Seasonality plays a very big role in business success in Chester. Our stores are surrounded by farms that reliably bring in business from agro-tourism every fall, so proper forecasting is essential when it comes to capitalizing on that demand.

This rings especially true for seasonal items like our candles, which are handmade by me and my brother-in-law. We do everything from wicking the jars to mixing the fragrance with the wax and pouring the candles. With that in mind, forecasting has been stressful. If we don’t make enough, we leave money on the table, and if we make too many candles, we waste our time and resources.

With Square AI, I can look through our sales data all the way back to 2017, when we opened our first store. I can track year-over-year sales and immediately see which fall scents were popular based on the numbers that spiked. Being able to project, order and actually make anything before the holiday season is so helpful, especially because some of our vendors run out of stock on supplies.

Lesson 3: Recognize that local events impact foot traffic

Because all six of our stores are located off of a main street, we heavily rely on foot traffic. Weather and local events can make or break the day.

When Square announced that Square AI was going to start incorporating web data, I was thrilled. There are so many events that I don’t even realize are happening, whether it’s at a school or one of the local farms nearby, so being able to anticipate these things is a game-changer. When we’re plugged into what’s happening, we’re able to focus on staffing up if we need to. It helps us provide the best experience for our customers, and I’m proud of that.

Anybody can go online and order a candle, but they get a personalized experience from us, and I love that Square AI helps us protect that.

Lesson 4: Keep an open mind when exploring customer patterns

Square has helped us rethink how we look at and deal with our data, which has given us the opportunity to dig into numbers. We simply would not have had the time to look at the data in this way before, so it’s great to use this tool to learn from and plan with.

Now we know that on average, returning customers spend more money at our stores than new customers, and we have answers to questions about purchase patterns across our locations. But before Square AI, I didn’t have time to figure out how to organize and sift through the numbers by location, customer type, day of the week and hour of the day.

We’ve been able to be more targeted with our marketing, launching flyers, emails and discounts for loyal customers in an effort to cross-promote our locations. We’ve already seen 10% more engagement, which is a pretty significant boost.

Time savings is the most valuable takeaway

By integrating Square AI into my every day, I get to spend more quality time with my friends and family, and I’m able to invest more energy in growing my business. It’s happening in real time. We opened a new store in September, and Square AI is helping me feel confident about my sales forecasting, projections and inventory management. I’m excited to build a new store using these insights from day one.

Ryan Hester
Ryan Hester, is the co-owner of Comfortably Chic, a local Main Street icon in Chester, New Jersey. Ryan works alongside his family running the multi-store retail business, focused on product, operations, and growth.

Related

Keep Reading

Tell us a little more about yourself to gain access to the resource.

i Enter your first name.
i Enter your last name.
i Enter a valid phone number.
i Enter your company name.
i Select estimated annual revenue.
i This field is required.
✓

Thank you!
Check your email for your resource.

x
Results for

Based on your region, we recommend viewing our website in:

Continue to ->