OpenTable + Square (again)

Square is now OpenTable’s ‘preferred point of sale partner’

Aug 18, 2026

Square and OpenTable are taking on the competition with a new digital guest profile that combines a diner’s reservation history, dining preferences and transaction data. Together, the companies say, the data will power stronger loyalty programs and personalized marketing campaigns. And it’ll drive better guest experiences during service, surfacing relevant diner info on Square’s handheld, the tableside point-of-sale devices used by servers.

The two San Francisco-founded companies first partnered in 2022 and have already connected reservations and point of sale data for restaurants. Today, they promise “deeper insights sharing… to address the restaurant pain point of disconnected systems,” per a press release.

“We believe in a seamless ecosystem and we believe in giving operators the best products we can so that it’s actually seamless,” James Schonzeit, head of food and beverage at Square, told me during an interview this week.

“The opportunity is bigger than simply connecting two systems,” said Robin Chiang, chief growth officer at OpenTable, over email. “Because OpenTable and Square’s engineering teams built the integration directly, the platforms communicate bi-directionally in real time — giving restaurants one continuous view of the guest from booking and arrival through ordering, payment and future visits.”

This might sound familiar.

That’s because top competitors to OpenTable and Square just rolled out a similar integration. Reservations service Resy and point of sale platform Toast announced a major partnership last year. Last week, they debuted (long awaited) Resy-powered digital chits — notes and info about a diner — to Toast handhelds.

Bookings are back in the discourse after a recent Wall Street Journal piece lamenting the state of the business “Reservation apps have made getting into a restaurant a nightmare,” its headline dramatically declared. “Nightmare” is a strong word for what’s happening to reservations — even in New York, considered the epicenter of reservations mania thanks to its density and probably its status as the onetime walk-in capital of America (as anyone who’s experienced a bit of NYC restaurant serendipity will tell you, this writer included).

But it is true that an increasing number of partnerships, arrangements, exclusive events, and status-driven access allow technology companies and their credit card benefactors to broker the relationship between restaurant and diner. Now additional info — data on customer spend, payment methods, visit history, and more — is creeping into in the (very visible) mix.

“Reservations, payments, and guest data shouldn’t be different systems that restaurant operators have to stitch together themselves,” Square’s Schonzeit said in a release. “No one has time for that, and we’re not in the business of gatekeeping their most valuable insights.”

After a tumultuous few months, Square is once again highlighting its capabilities at full-service restaurants.

A deal with the country’s top reservations platform brings Square serious visibility. It’s now OpenTable’s preferred point of sale partner.

“We expect this collaboration will accelerate our customer acquisition efforts,” execs wrote of the deal in Square’s August letter to shareholders.

Last February, Square parent company Block laid off half of its workforce, some 4,000 workers including its then-head of restaurants and much of his team. Just hours after employees received notice that their roles had been cut, Block’s executives extolled Square’s progress inside restaurants in the company’s fourth-quarter earnings call, flagging a year-over-year increase in gross payment volume — total transaction value — at restaurants and other food-service vendors using Square’s point of sale.

Six months later, gross payment volume from restaurants and other food businesses on Square is up again, this time 20 percent year over year. GPV in the US accelerated to its strongest growth rate since early 2023.

Square got its start with small, independent businesses and still thrives in places like coffee shops and food trucks. But it’s expanding fast. Earlier this year, it added a new drive-thru product, targeting multi-location quick service restaurants. In Block’s early August earnings call, chief financial officer Amrita Ahuja called “mid-markets” — businesses processing over $500,000 through Square annually — the company’s “fastest ramping segment,” growing over 20 percent.

This makes it a great time to highlight the company’s ability to serve full-service restaurants — and their guests. And the companies promise there’s more to come from its OpenTable deal: “Future enhancements,” Square’s press release promises, “will focus on faster onboarding, smarter reservation workflows, richer guest intelligence across every ordering channel, and deeper integration of loyalty, customer engagement, and payment experiences.”