Square Launches Built-In AI Assistant for Canada’s Small Businesses

With 60% of Canadian entrepreneurs already using AI tools, Square AI turns everyday business questions into instant answers — at no additional cost

Today, Square announced the launch of Square AI in Canada, a new built-in AI assistant that helps small businesses turn instinct into action by backing it with clear, conversational insight at no additional cost.

Small businesses are often built on instinct. Owners rely on experience, knowledge, and gut feelings to make decisions every day. Validating those instincts with data has often required time and tools that many small businesses simply do not have.

Square AI changes that. Small business owners and operators can ask natural questions about their business such as “Which items sell best on weekends?” or “How did last month compare to the one before?” By making insights as easy as asking a question, Square AI helps sellers move faster, decide with confidence, and focus on what matters most: running and growing their business.

“Before, I had to go into dashboards, filter data and build spreadsheets to understand how items were performing at different times of day,” said Nadiia Semenichenko, Regional Manager at 10 DEAN, a Toronto multi-location café and bar that had early access to Square AI. “Now I just ask a question and it builds the table for me. Square AI has definitely changed how we review performance and make decisions day to day.”

Canada’s Small Businesses Are AI-Ready

The launch of Square AI is supported by global research commissioned by Square that surveyed approximately 4,000 business owners across eight countries. The findings show Canadian entrepreneurs are among the most pragmatic and open-minded AI adopters worldwide.

Nearly three in four Canadian business owners (74%) say they are already familiar with AI tools that could support their businesses, while 60% have already adopted AI. The majority of Canadian respondents agree AI has the potential to save time that can be reinvested into improving work-life balance (38%), developing new ideas to grow their businesses (37%), improving marketing (31%), and spending more time with customers (26%).

“Across our markets, we’re already seeing businesses use Square AI to get clearer on their performance, make faster decisions, and spend less time buried in reports,” said Willem Avé, Chief Product Officer at Square. “Businesses generate enormous amounts of data every day through payments and commerce. For a long time, turning that data into real insight has been something reserved for larger organizations with analysts and operations teams. Square AI levels the playing field by bringing powerful analytics into the flow of running a business through a simple, conversational AI assistant. It allows businesses of every size to combine their instinct with real data, without complexity.”

New Tools to Help Canadian Restaurants Run Smarter

In addition to Square AI, Square is launching a suite of new tools for Canadian food and beverage businesses designed to streamline operations and improve the guest experience at a critical time for the industry:

• Seat Management empowers servers to manage tables their way by handling last-minute guest additions and seat changes with ease, while keeping service flowing smoothly and maintaining order accuracy — all from one intuitive platform.
• House Accounts makes it easy for sellers to offer trusted customers the convenience of paying later, with clear visibility into balances and simple invoicing to support faster reconciliation and repeat visits.
• Square Register (2nd generation): Building on the success of the original Square Register, the revamped hardware delivers improved speed and reliability, with a point-of-sale system that’s 40% faster and more durable, helping sellers seamlessly manage operations, deliver high-quality customer experiences, and keep orders flowing during their busiest periods.
• Square Restaurant Inventory by MarketMan: Gives restaurants real-time visibility into inventory across one or multiple locations, automates reorder alerts and supplier management, and integrates directly with Square POS to reduce waste and improve cost control.

To learn more about Square AI and how it’s helping Canadian businesses thrive, visit https://squareup.com/ca/en/ai.

About Square
Square helps businesses turn transactions into connections and businesses into neighbourhood favorites.

In 2009, Square started with a simple invention – the first mobile card reader, which changed how the entire financial system thinks about small businesses. Square has since grown into a global business platform helping millions of sellers of all sizes participate and thrive in their communities.

Whether independently run or a global chain, Square understands that sellers succeed when they have the freedom to focus on the experiences that keep customers coming back. From point of sale and payments to online commerce, staff management, embedded financial tools and more, Square brings together the tools sellers need to run and grow on one intelligent platform. For more information, visit squareup.ca.

About the Survey
The global research from Square was conducted by Censuswide among approximately 4,000 businesses across Australia, Canada, France, Ireland, Japan, Spain, the UK, and the United States.