How to use AI Agents with Square?

[cscstore]

Hey Square Community!

• We wanted to ask if anyone has any experience using Artificial Intelligence (AI) Agents in their businesses running on Square?
  • An artificial intelligence (AI) agent is a system that autonomously performs tasks by designing workflows with available tools (according to IBM).
• If so, how has it worked out?

We're currently at a point in our business where day to day operations are outpacing the amount of people we have to fulfill some tasks, and we're researching some alternatives to lighten the load.

AI Agents have come up during our research, and wanted to see if anyone had experience using them. Most of what we found centers around services like n8n, Make AI, and Zapier.

We're a retail clothing business and we also offer printing services for the blank garments we sell.
We were thinking the AI Agents could be helpful in keeping up with communication with our vendors and customers, as well as potentially looking over our inventories to see what needs to be restocked.

I'm sure there are other ways AI Agents could be used, so any advice or experience would be greatly appreciated.

Thanks for taking the time to read and respond! 😄

[Ellie_]

Hi there, @cscstore,

You're definitely not alone in exploring automation and AI to help manage growing operational demands. We’ve seen a number of Square sellers start experimenting with AI-driven tools like n8n, Make, and Zapier, especially when combined with Square’s APIs and integrations. You might also want to check out Square App Marketplace to explore AI-compatible tools and integrations that are already vetted to work well within the Square ecosystem. We’d love to hear how your journey with AI unfolds, and we encourage other sellers in the community to share their experiences, too!

[Ellie_]

Hi there again, @cscstore,

I just wanted to send another update to you about your questions regarding Square and AI. Along with the products I mentioned before, I recommend looking into Square AI. Square AI is a new product from Square that lets you ask direct questions about your business data, as well as about Square’s products. Sellers use it to drill into questions about what items are trending, busy vs. slow hours during particular time periods, and all kinds of “what if” questions you might get at a high-level in a report but want to dig into the details. You can read all about the feature here on Square's Support Center, or see a step-by-step 5-minute walkthrough video here. You might also be interested in learning more from other sellers and how they're using it, which you can read about on The Bottom Line here.

We’d love to hear how your journey with AI unfolds, and we encourage other sellers in the community to share their experiences, too! @TheRealChipA was an early beta tester for Square AI, and loves to share his experience, so feel free to ask about their thoughts!

[Donnie-M]

@cscstore I think the reason you see zapier is the automated ability to get information from the square api about transactions so you can take the information out of square and feed it back in with a back end utility.

Where it actually works today:

• Inventory monitoring: You can connect Square’s Inventory API to an AI workflow (Zapier, Make, or even a lightweight Python script on your own server). The agent can scan stock daily and send you a message: “You’re down to 8 white medium tees, reorder?”  Think of it like if this then that trigger.

• Vendor/customer communication: AI + Zapier can auto-reply with order confirmations, or draft messages that you approve before sending. It works best as a draft assistant (you review before sending) rather than fully autonomous, especially in retail where tone matters.

• Reporting: You can ask an AI layer (through Square’s data exports) questions like “Which SKUs are trending up week over week?” or “What’s my margin on custom prints vs blanks?” It’s like having an extra manager that never sleeps.  Now this is where the built in square Ai assistant can already help.  I would give it a run around and just ask questions, whatever comes to mind, and see what you get, experiment.

Where to be cautious:

• Full autonomy is tricky, AI still makes errors. Let it suggest or summarize, then you click “send” or “order.”

• You’ll want clear guardrails.  The more detailed the better they work.

Best starting point for your use case:

• Connect Square → Google Sheets → AI Agent. That gives you visibility into sales/inventory, while the AI suggests reorders or flags trends.  Look in the settings they are starting to integrate directly.

I think of AI Agents as cheap assistant managers: great for triage, reminders, and grunt work, but you still want a human approving the final moves.  If it is something you are already good at, it might not make you better, but you can maybe automate things to speed it up for you.

The way Square has integrated the AI into descriptions for items, has made it where I can let managers add special items and not worry about re-writing every description.  If it isn't perfect, no problem, but it is 95% better than someone not experienced in item descriptions.

I am not moving to AI analyzing staffing, SOP, par times, par levels, etc.  Back of house stuff.  I am also using it to train my managers and make them better at what they do.  I don't have to teach food cost with AI.