Summer 2026 is shaping up to be a season defined by artificial-intelligence-centered initiatives and partnerships for Square, a California-based restaurant technology platform with more than 450,000 food and beverage business partners.
Square announced a ChatGPT app and Claude plugin July 1, automatically enrolling Square Food & Beverage sellers with activated Square Online Ordering profiles to route agentic orders directly into existing Square Online Ordering setups.
Additionally, AI-powered guest engagement platform Incentivio announced an integration with Square June 29, enabling restaurant operators to connect menus, ordering, loyalty solutions, marketing, gift cards and other reporting across in-store and digital channels.
Square’s chatbot integrations
Consumers are increasingly turning to AI chatbots, with 24 percent of U.S. adults using such platforms daily and 49 percent every week, according to a June 17 report from the Pew Research Center.
More than 40 percent of consumers now turn to AI tools for assistance with shopping — including discovery, comparison and selection, according to May 5 research from NielsenIQ. Additionally, Morgan Stanley estimates from late 2025 found that agentic shoppers could drive about $385 billion in U.S. ecommerce spending by 2030.
Square’s integrations with ChatGPT and Claude allow chatbot users to discover participating restaurants, browse menus and place orders through Order by Cash App. Those orders route directly into sellers’ Square online ordering solutions, including POS and kitchen display systems.
Participating operators manage AI discoverability through the Square Dashboard, while Square executes infrastructure-focused tasks in real time, such as syncing business information, menu data, operating hours and ordering information.
Square’s AI chatbot integrations come at no additional cost to participating operators — no commissions or additional fees for agentic orders.
Morgan Kuntze, global partnerships lead at Square’s parent company, Block, described the integrations as an effort to ensure restaurants can avoid “playing an impossible game of catch-up” in the rapidly shifting agentic ordering space.
“Our investment into agentic commerce aims to offload that responsibility by giving operators time back, helping connect them with customers in their communities and keeping them at the industry’s cutting edge,” Kuntze said in a press release. “Modern commerce is moving at a sprint, and we’re building Square to help sellers appear everywhere customers are going.”
ChatGPT and Claude are the first- and sixth-most-used AI chatbots among U.S. adults, respectively, according to the aforementioned Pew Research Center report. Still, Square is working to capitalize on additional emerging ordering channels, including Amazon’s AI-powered Alexa+.
Incentivio’s integration with Square
Incentivio’s integration with Square brings the Boston-based engagement platform’s commerce, engagement and intelligence capabilities with Square’s POS infrastructure. As a result of the integration, menus — including items, modifiers, pricing and availability — automatically reflect across web and mobile ordering channels.
“Square has built a flexible, widely adopted POS platform for restaurants, and this integration extends its capabilities by unlocking deeper guest engagement,” Sash Dias, Incentivio’s chief operating officer, said in a press release. “By combining Square’s in-store strengths with Incentivio’s ordering, loyalty and marketing platform, restaurants can create more connected experiences while improving performance across every location.”
The integration offers Incentivio’s AI-powered recommendations to Square restaurant partners, promising data-driven upsell suggestions across digital channels. Additionally, the integration allows restaurants to capture guests in-store, creating unified guest profiles so operators can deliver promotions across email, SMS, push notifications and in-app messaging.
