Running a small business can mean spending the day serving customers and the evening figuring out what happened. Square is pitching its latest AI tools as a way to cut down on that second shift, with an assistant that can do more than summarize a spreadsheet.
The company has announced Squaremates, an evolution of its Managerbot assistant that is becoming the main way sellers experience Square Dashboard when signing in. Available to eligible U.S. sellers at no additional cost, it can handle work involving multiple steps, generate usable materials, and help owners figure out what needs their attention.
Look, folks, another chatbot telling a restaurant owner that Tuesday was slow is not especially exciting. An assistant that investigates the problem and prepares something the owner can actually use is a more compelling proposition, provided its work holds up.
Square says Squaremates can examine sales over a particular period, identify customers who have stopped returning, and generate a marketing campaign or discount aimed at bringing them back. It can also review a product catalog and make bulk changes to prices, descriptions, images, and visibility across sales channels.
Staffing is another target. Squaremates can compare labor costs against sales and produce a proposed schedule for the seller to review. That could save some spreadsheet time, although an owner still needs to account for things that sales figures alone cannot explain, including employee availability and what it takes to keep a location running properly.
Square is also emphasizing the outputs its assistant creates. Instead of leaving the owner with a wall of chat text, Squaremates can produce a graphical sales breakdown or a designed email campaign that matches the business’s branding. The useful question is whether those materials need a quick review or another hour of fixing.
“Running a business is an endless string of judgment calls that are all on the owner,” said Willem Avé, Square’s Global Head of Intelligence. “How to price a new menu item, whether to add a shift, what to do about a slow week.”
Some of the more ambitious features are still being developed. A restocking capability currently in beta can identify low inventory, prepare an order, and build it on a supplier’s website for the seller to complete. Square also says permission-based email access is coming, allowing daily briefings to combine inbox items with information about the business.
Those availability details are worth paying attention to. The supplier ordering feature is in beta, while the inbox integration is described as coming soon. Square’s stated approach is that the assistant does the preparation and the seller decides what goes ahead.
Businesses that already use other AI assistants have options too. An improved Square MCP and new Square CLI let outside tools connect more directly to Square, potentially reducing the routine of exporting business data and uploading it somewhere else for analysis.
Square MCP, short for Model Context Protocol, lets a connected third-party assistant ask questions and make changes through a defined set of Square actions. Square CLI provides command-line access to Square’s APIs for sellers and developers who want to script tasks, schedule work, or build their own tools.
The company is also introducing Squaremates Apps. Sellers can describe an application to Squaremates or use Square CLI with an AI coding tool, then deploy and host the resulting application on Square. Suggested uses include dividing cash tips according to hours worked and displaying staffing information across several locations.
Custom software for those everyday problems could be the most interesting part of this announcement. Plenty of businesses have a recurring task that is too specific for a standard dashboard but too small to justify a traditional software project. Whether AI makes that practical will depend on how reliably the resulting app works and how easily someone can maintain it.
Square says Squaremates, Square MCP, Square CLI, and Squaremates Apps are available to U.S. sellers at no additional cost. There is an eligibility exception, however: Squaremates is not currently available to Multi-Account Suite sellers.
A separate Squaremates mobile app built on Buzz is also planned, combining team communication, task management, and AI agents. For now, Square is offering a waitlist for alpha access, so that app should not be confused with the tools available at launch.
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