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Square Expands Agentic AI Tools to Give Sellers More Control Over Business Operations

Square launches 'Squaremates' AI to help merchants automate back-office tasks and analyze sales data through a proactive virtual assistant.

Curated by Financing Your Way from original reporting by PYMNTS. Summary is AI-assisted and editorially reviewed — see our editorial standards.

FYWBy Financing Your Way EditorialNovember 12, 2026

Square is integrating advanced 'agentic' AI directly into its merchant dashboard. For retailers and service providers, this means the software is moving beyond simple data tracking. The new 'Squaremates' tool acts as a virtual business partner that can perform tasks, not just answer questions. It integrates with your sales data to provide instant insights into customer spending habits and payment trends. What matters most for your business is the automation of back-office workflows. The AI can now draft marketing campaigns based on purchase history and help manage inventory more accurately. For businesses using Square for financing or payment processing, these tools are designed to reduce the time spent on administrative labor. Square is also allowing these tools to connect with outside AI assistants, meaning your business data can flow more easily between different platforms you use to stay organized. This shift signals a move toward 'hands-free' business management where the system proactively suggests ways to increase sales and streamline operations.

Source: PYMNTS

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