Actionable Intel, Faster Support, and Pathways to Growth: Early Insights from Square AI

By Willem Avé, Global Head of Product

At Square, we believe that AI has the power to fundamentally reshape commerce, and that sellers of all sizes should benefit from the insights, efficiencies, and time savings that it can offer. We also believe that sellers, as the ultimate experts of the day-to-day challenges of operating a business, should play an active role in the creation and betterment of the AI tools designed for their needs. That’s why, at the end of May, we launched Square AI in open beta, bringing sellers a conversational AI assistant embedded in Square Dashboard that’s designed to answer their critical questions – about their business, their teams, their customers, or the Square products they use – all through pairing data visualization with a natural language interface that we’re rapidly iterating on.

Over the first two months, tens of thousands of sellers in the US have already asked Square AI about topics ranging from item performance and historical revenue trends, to staff management and customer insights. Questions come from all types of sellers, from solopreneurs and part-time sellers to national chains and franchises, with larger sellers showing the highest rates of adoption and engagement.

In addition to using Square AI as an always-on support resource for product assistance and troubleshooting help, 60% of Square AI queries have focused on business operations, showcasing sellers’ desire to use AI to uncover the underlying trends and insights that will help them make better, more informed decisions. The focus on addressing real-world, real-time needs is what we’ve always envisioned for Square AI, and speaks to why Square is uniquely positioned to bring this type of innovative solution to sellers, directly integrated into the same technology they use daily, powered by the same platform that millions of businesses trust.

Insights and Real-World Impact

The early engagement numbers paint a compelling picture: in addition to the high volume of queries asked by sellers, the majority of questions come from sellers with multiple locations. In fact, every measure of business complexity correlates with higher engagement — whether the seller has more locations, more employees, or simply more revenue, bigger and more complex sellers just have more questions, and answering those questions translates into real impact.

Donnie McClanahan operates four cafes in Knoxville, Tennessee, including Order Up Cafe and Tombras Cafe, and has likened his experience of querying Square AI to talking to his accountant, only faster. Recently, Donnie was considering removing a couple items to simplify his menu. Before making a decision, he used Square AI to quickly check what percentage of his sales came from those items and realized they were actually outperforming his assumptions and carrying the lunch shift. That one interaction with Square AI stopped him from following a hunch that would have hurt his bottom line. Beyond item performance, Donnie has also used Square AI to analyze revenue and labor costs by time of day, with one session leading him to realize he could shift opening time back by 30 minutes at one of his locations to save on costs while not meaningfully impacting revenue.

Donnie explains why this is such a big unlock: “AI changes how we interact with our data. We can finally talk to our numbers in natural language, and the AI actually understands us, typos and all. That’s not just tech; that’s a new relationship with your business.”

Across our open beta, the biggest takeaway has been that while Square AI certainly saves sellers time, its real superpower is amplifying the curiosity that makes entrepreneurs so effective. Whether it’s optimizing hours for specific Fridays during specific months, getting fast insights on a new item, or identifying the top customers for every location every week, sellers are running granular reports in minutes that used to take hours – or more commonly, never happened at all.

AI for Sellers, Built with Sellers

When we launched Square AI in open beta, we made a commitment to building the product alongside our sellers. Over the past two months, we’ve brought this commitment to life in a number of ways, including hosting dozens of early adopters and AI-curious sellers at the Corner Store in San Francisco. Over an evening of conversations and demos, sellers detailed the creative ways they’ve been leveraging AI, shared practical tips with other businesses, and provided us with valuable feedback on how to make Square AI an even more powerful tool to help them tackle their operational challenges. Throughout our entire open beta, we’ve actively engaged with sellers from around the country in our Seller Community forums to better understand their questions, concerns, and overall views on using AI for their businesses.

Across all of these conversations and touchpoints, we’re seeing sellers leverage Square AI to power their curiosity, question assumptions they’ve made about their business, and quickly source the knowledge they need to optimize the way they operate. As we build and develop new functionality, we’ll continue to rely on the needs and insights of sellers to guide our roadmap – working to transform Square AI from a conversational AI assistant into an always-on business partner.