Square launches ChatGPT app & Claude plugin for sellers

Square has launched a ChatGPT app and a Claude plugin for sellers. The initial rollout covers eligible US food and beverage merchants using Square Online Ordering.

The integrations are designed to help businesses appear in AI conversations where customers are deciding where to eat, shop or book services. Participating restaurants can be discovered, have their menus viewed and receive orders through those channels, with transactions routed into their existing Square systems.

Orders placed through the integrations flow into Square Online Ordering, including the point-of-sale and Kitchen Display System tools sellers already use. The source of each order appears in reporting, allowing operators to track how the channels perform.

A key part of the launch is pricing. Square will not charge additional marketplace commissions on orders placed through the ChatGPT and Claude integrations, setting the offer apart from many food delivery platforms that take a share of each sale.

Eligible sellers also do not need to build an API, configure a separate product or pay extra fees to take part. Business information, menus, opening hours, and ordering data are synced via the Square Dashboard, while Square manages the underlying connection to AI services.

First sector

The first businesses to go live are US Square food and beverage sellers with an activated Square Online Ordering profile. Customers place orders using Order by Cash App, and those requests then enter the merchant's existing order management flow.

The move reflects a broader push by commerce platforms to ensure merchants appear wherever consumers begin their buying journey. Search engines, maps, social platforms and online marketplaces have long played that role, and AI chat assistants are becoming another entry point.

Square cited research showing that more than 42% of consumers now use AI tools for shopping tasks such as product discovery, comparison and selection. It also cited estimates that agent-driven shopping could account for USD $385 billion in US eCommerce spending by 2030.

The product is aimed at small and medium-sized businesses that may not have the resources to build direct integrations with each new AI channel. Instead, sellers are enrolled through Square's existing system, with AI discoverability controls handled in the dashboard they already use.

Wider push

ChatGPT and Claude are the first live integrations, but not the only ones in development. Square is also working with Amazon to bring sellers into Alexa+ experiences, extending the same model into voice-led shopping and ordering.

The strategy suggests Square wants to act as an intermediary between merchants and a growing list of AI platforms. Rather than asking each seller to manage separate technical connections, it is building a shared infrastructure layer that can distribute business data and ordering information across multiple services.

Square already serves more than 4.5 million sellers across search, maps, social and marketplace channels. The new AI integrations extend that distribution model into conversational interfaces, where customers may ask for nearby restaurants, compare options or complete an order without leaving the assistant.

The company has also joined several groups working on standards for agent-led commerce, including the AAIF Agentic Commerce Working Group, the W3C Web Payments Working Group and the Universal Commerce Protocol. There, Square is working with Google on a specification for local food ordering and delivery.

According to Square, that protocol is intended to support discovery and checkout across Google products, including Search, AI Mode and the Gemini app. The aim is to help sellers tap into those systems as they expand into more categories.

Merchant feedback

Square worked with Partners Coffee, a Brooklyn-based coffee business, to test how AI-driven discovery surfaces merchant information and what customers want to see in those interactions.

"We don't see coffee as transactional. To us, it's an opportunity to pause and reflect, a chance to unwind, and a catalyst for connection," said Andrew Costaris, digital VP at Partners Coffee.

"We encourage individuals to visit our cafes as a reprieve from the busyness of everyday life. The last thing we want is for our technology solutions to work against this mission or complicate the customer experience."

Costaris said the system plays a background role in the business.

"What Square has built not only allows our team to continue offering analog, experiential moments; it creates more of them," said Costaris. "With agentic commerce and AI tools working in the background, we're confident knowing that our business is being digitally discovered and is consistently growing in efficiency, while our customers can continue to enjoy a lo-fi, specialty coffee-first environment."

Square's broader pitch is that merchants should not have to keep rebuilding their digital presence every time consumer behaviour shifts. "Consumer behaviors and preferences are constantly evolving, and business owners can easily find themselves playing an impossible game of catch-up," said Morgan Kuntze, Global Partnerships Lead at Block.

"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. Modern commerce is moving at a sprint, and we're building Square to help sellers appear everywhere customers are going," Kuntze said.