Square AI, Now in Open Beta, Unlocks Business Insights

By Willem Avé, Global Head of Product

At Square Releases last month, I introduced the latest step in our AI journey, Square AI. Square AI starts small, with a new conversational AI assistant integrated directly into Square Dashboard. It is available now in public beta for all sellers* in the US.

Now, when a seller visits their dashboard, they can simply ask questions about their business using natural language, and receive instant, direct answers. Square AI interprets the question, digs through relevant data within Square, and surfaces the answer – saving sellers from digging to find the right report, knowing how to set the right filters, or spending time combing through rows of data.

Business owners frequently tell us about the “what-ifs” that keep them up at night and the “what-abouts” that drive them every day. While these questions often take a backseat to day-to-day concerns, they can unlock opportunities to meaningfully streamline operations and increase margins. Our goal is to enable sellers to solve daily problems like optimizing staff hours, identifying slow-moving inventory, maximizing top sellers, or recognizing top customers. The types of questions that can make or break a business, vary from business to business, and can change from week to week.

How it works
This latest Square AI feature surfaces as a conversational chat experience within a seller’s Square Dashboard. Today, sellers can ask Square AI about their sales, customers, staff, and transactions, and we’ll be steadily expanding capabilities throughout the year.

For example, sellers may ask to dig into:

• Sales metrics and trends – “What were my best-selling items between 4pm and 5pm yesterday?”
• Transaction analysis – “Show me voided transactions from last weekend.”
• Staff performance and labor costs – “Which employee had the most overtime hours last month?”
• Customer insights and spending patterns – “Who are my top 10 customers this quarter?”

We believe the best data exploration is conversational. We want to enable sellers’ curiosity to understand different parts of their business. Once they find an answer they’re satisfied with, they can easily download insights as a CSV or explore deeper with contextual visualizations (pie, line, or bar charts). Letting their curiosity drive, sellers can continue the conversation and drill down further into any finding. Square AI retains the context of the conversation, so users don’t have to restate any of the previous questions, making it easier than ever to arrive at those critical, granular insights that can shape important business decisions. And users can also multi-task by navigating around the Square Dashboard as the chat window continues working on their behalf.

Square AI can also answer any help and operational questions about using Square. Just ask it how to do or where to find something within Square, and it will automatically comb through its knowledge base and provide you with step-by-step instructions so users don’t have to search for an article or contact support.

Our goal is to give each seller their own virtual employee that knows every bit of their business. We’ve built innovative technology that reduces hallucinations and enables the system to understand a seller’s data deeply, so they can more easily ask the questions and discover the insights that can empower them to grow their business and operate more effectively.

When it comes to data security, we’ve taken special safeguards to never send highly sensitive business or financial information to any model providers or partners, and established dedicated enterprise agreements to ensure no data processed by third party companies is ever retained for any purpose outside of Square systems, nor used for any type of training. This is a distinct difference from the public AI chatbots many owners, managers and employees are already using personally. With Square AI, sellers can trust that their data is protected by the same security infrastructure that safeguards billions of Square transactions.

Reimagining the future of commerce with Square AI
This isn’t the first intuitive AI feature we deliver to sellers, and it won’t be the last. AI-powered content creation, onboarding and setup features are already widely integrated across Square. Every day, restaurants and service providers are automatically generating and updating menus with descriptions and prices; retailers are instantly creating catalogs, website copy, and images for their online storefronts; and sellers are personalizing content copy for their communications to staff and customers, all using native generative AI tools within Square.

We’re still just getting started.

We also recently introduced the Square MCP server, which standardizes how Square connects and provides context to large language models such as ChatGPT or Anthropic’s Claude. While these MCPs still require some technical know-how today, and are currently most used by developers, we are fast-approaching a world where any neighborhood business can just ask for the tools they need, and AI brings them into existence on-demand, personalized for the nuances and quirks of their business. In fact, we are already seeing sellers with zero programming experience use these models to build small tools – custom inventory forecasting, catalog organizers, and more – across Square’s full API platform.

We look forward to seeing how our sellers unlock new insights and growth through AI, and to building Square AI alongside them.

*To protect sellers’ business data, usage of Square AI is only available for account owners and admins. If you would like to learn about how Square processes data for use with AI tools, read our privacy notice.