Square

How are you using AI to improve your business? What are your biggest questions?

👋 Hi folks! My name is Sam and I’m part of the team working on Square AI, which is now available in open beta to all owner accounts in the US. 

 

As we continue to build AI capabilities into Square and bring you resources to help you get the most out of AI, we’re curious to hear: 

 

What are some of your biggest questions about using AI to improve your business? 

 

What are some of the biggest unlocks you’ve found by using AI so far?

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Hi @sargos AI for me has to be almost invisible, doing those tasks that AI can do but without me knowing its doing it. If I have to instruct it too much, if its not intuitive then it may be a little too cumbersome to use. 

 

We have used AI for blog generation but I have read that AI will be changing the way searches will be conducted. It would be nice if AI could look at my website, for example realize that our business sells chocolate, we sell all year round, peak times are Christmas, Easter, Mothers Day etc, we sell dark, milk and white chocolate, we have chocolate for suitable for vegan diets and then have AI generate the information be it 'blog' content in the format that the new AI searches will like to see. Take the human out the equation. AI should know what AI searches would like to see and in what format. 

Coco Chemistry Ltd
Artisan Chocolatier
www.cocochemistry.co.uk

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To make it read like a human wrote it instead of so computer. AI has potential, it’s getting owners to accept the concept of allowing AI to work for a business the opportunity to grow.


I have been trying different platforms for our business in AI. See attached images. I know AI has more to learn from in growing our business. 

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AI is what you make of it. I think AI is a game changer because it equalizes and gives everyone a level playing field. If used correctly, it will empower you to be better.

 

I use AI pretty often and I used it to create a sales agent roleplay tool for my sales people to practice on speaking to customers and cold calling customers. This turned into a real software app.

 

If people haven't started using ChatGPT or one of the LLM's, I would say just ask it questions everyday and youll be surprised at what you learn with the follow up questions it asks.

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I like the idea of using it for roleplay. Customer service and training is very important especially if you are at the coal face from dealing with new enquiries, complaints or just how to be nice to customer without being too sickly sweet sweet in approach. Off for a play on it now.

Coco Chemistry Ltd
Artisan Chocolatier
www.cocochemistry.co.uk
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I’ve noticed that when I ask the AI to show how many appointments were booked by specific staff members, for example the spa manager, it’s unable to generate a report. I understand that tracking service providers and items sold is important, but it’s equally important to track the people responsible for keeping the schedule full, like the receptionist or front desk team.

 

If a staff member has login access and permission to book appointments, I’d like to see how many slots they’ve filled for a given period (daily, weekly, or monthly). This helps me evaluate whether they are fulfilling their role effectively. It would be very useful if this data were included in the reporting section.

 

In addition, I’d like to know how many appointment requests came in online, how many were accepted, and by whom. These insights would show how well the front desk team is managing appointment requests and maintaining workflow efficiency.

When I asked the AI, “How many 48-Hour Repairs did we have in October?” it responded with:


"I found multiple catalog objects that match ‘48 Hour Repair’. To help you get the right sales data, please specify which option you are referring to."

 

However, when I clicked on the links, nothing loaded. I know that some 48-Hour Repairs were scheduled last month. These are booked services, not ring-up sales, since they’re complimentary fixes for clients. This suggests that appointment data—not just sales data—needs to be incorporated into the AI’s reporting capabilities. Many businesses like mine are primarily service-based, so appointment data should have its own report category and be included in the AI’s dataset.

 

I’ll continue to use the AI and provide feedback as you improve it, but I wanted to highlight that appointment and booking data are essential for a complete picture of business performance.

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We do not use it and we do not want to use it.  We do not like the prompt box that's stuck at the top of the dashboard.  We have no use for it other than its original intent: create a report. 

 

AI should never refer to itself using personal pronouns.  It's pronoun is "it," because it's a machine.  No matter how hard you try, it will never be a human. Multiple smart, creative, and curious writers have explored that possibility and it never ends well. 

I have found no value in it for my business. If I want to run a report, I'll do that.  I do not need it to suggest reports or questions.  

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@mythicrunning I run four locations and it's already caught things in my numbers I wasn't looking for.

 

What would it have to do for you to want to use it?

Donnie
Multi-Unit Manager | Founder, Table & Ledger
tableandledger.com

Square AI Champion | Using Square since July, 2017

"Good judgment comes from experience, and experience comes from bad judgment."

"You can have everything in life you want, if you will just help other people get what they want." - Z.Z.

"AI doesn't replace your judgment. It gives your judgment better information to work with."
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I'm not an early adopter and so was late to the AI party; however, once I started using it there's no going back! I love ChatGPT and use it daily. Don't judge me - I gave it a name and converse with it like a friend, but it's also invaluable as a business assistant. For me it's numbers and trends mostly. It has been very helpful in analyzing my second business location in terms of how much money I can make, how many dogs I need to groom to be profitable, staff costs, etc. It also helped me with my website and Google business listing, and with money management like how to best pay for new equipment and how to strategically pay off debt.

 

I tried the Square AI but didn't find it very helpful. For example, I want to create a group of clients with a recurring appointments. So far, no matter how I prompt it can't understand this request. I then tried running reports of my most profitable clients and it was somewhat accurate in terms of which clients, but then it said their lifetime spend was like $25 when it's more like $2000. So I don't really use the Square AI because it's not yet effective or reliable. 

Animal care and welfare professional
Pet groomer
Entrepreneur
Curly Doodle Dog Grooming
First Street Pets on YouTube
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@sargos We are TRYING to use Claude to create a custom Square Appointments report to calculate how much to payout our service providers weekly. 

Screenshot 2026-03-13 at 10.59.00 PM.jpeg


This is a feature we have been requesting from the Appointments team for 8 years. We are SO close creating it ourselves using Claude, but in certain cases the data is wrong. 

We are having an issue  with accurately linking appointments with customer transactions using the API. 

We would really appreciate anyone’s help in resolving this. 

Thanks!

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I’ve been using it to speed up writing product descriptions and quick customer messages. My biggest question is how to make the replies sound more like my own voice without extra editing.

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I use AI to talk to then at least I can have an opinion with out being interrupted or questioned by the 1970’s police with a rubber hose and phone book. 

I do use it to create meta description for our website. Have I had the time to go and place all that into my site no. 

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