Before Checkmate became a platform serving thousands of restaurant brands, Vishal Agarwal was chasing a much simpler idea: helping diners receive their bill, swipe to pay on their phone, and head out.
The idea came while he was sitting in an airport restaurant, rushing to catch a flight but unable to find a way to pay his bill.
“I was about to miss my flight because I couldn’t find the way to pay my check,” Agarwal said.
His solution was a mobile app that would allow diners to receive their bill, swipe to pay, split it with friends, and walk out. The concept even inspired the company’s name.
But when Agarwal began pitching the product door to door to restaurants in New York City, operators quickly showed him a different problem.
One restaurant owner pointed behind the counter. Instead of focusing on guests, employees were juggling a stack of delivery tablets from platforms like Grubhub, DoorDash, and Uber Eats.
“All my guys are doing at lunchtime is accepting orders on these tablets and punching them into the POS,” the operator told him.
The Pivot
That moment forced a pivot. Rather than focusing on mobile payments, Checkmate shifted toward integrating third party delivery platforms directly into restaurant point of sale systems. The goal was simple: remove the wall of tablets separating staff from customers.
Today, that pivot powers a platform that has processed more than 700 million orders and supports over 2,400 restaurant brands.
Ironically, the company’s first major enterprise customer came from another moment of timing and conversation.
While attending a conference in Dallas during the early days of the company, Agarwal stepped into an elevator while answering customer support messages on his phone. Standing next to him was the head of IT for Five Guys.
The two started talking.
“He said, ‘What do you do?’” Agarwal recalled. “I said we integrate third party platforms like Uber Eats and DoorDash directly into restaurant POS systems.”
He asked a simple question: could Agarwal come downstairs to meet the rest of the Five Guys team?
A True Elevator Pitch
“That was our first enterprise client,” Agarwal said. “This is a true elevator story.”
The experience shaped how Agarwal thinks about selling technology to large restaurant brands. Enterprise operators rarely adopt new tools on someone else’s timeline.
“You don’t sell to enterprise,” he explained. “You make yourself available. They buy on their buying cycle.”
For Checkmate, that has meant focusing less on pushing software and more on solving real operational problems for restaurant brands.
Most Overlooked Operational Challenge
That philosophy extends to one of the industry’s most overlooked operational challenges: managing menus across a rapidly expanding set of digital channels.
Traditional point of sale systems were built for a time when most orders happened inside the restaurant. Today, operators must manage menus across delivery marketplaces, mobile ordering platforms, kiosks, digital menu boards, drive thru lanes, and first party websites.
Yet most POS systems still treat the menu as a fixed structure.
“The menus live inside the POS,” Agarwal said.
Checkmate’s approach extracts the menu data and allows operators to tailor how it appears across each digital channel, helping restaurants maintain consistency while optimizing how their menu performs wherever guests order.
For Agarwal, the goal of technology in restaurants is simple: remove friction so operators can focus on hospitality.
Digital Hospitality At Its Core
“Digital hospitality means being available to your customers where they are comfortable,” he said.
Some guests prefer ordering from a kiosk. Others want to speak to a person at the counter. Others will place their order from their phone before they even arrive.
Great hospitality means giving guests those choices while making the experience consistent across every channel.
And for Agarwal, the lesson from the company’s earliest days still applies.
Show up, solve real problems, and always be ready with your elevator pitch.
National Restaurant Show 2026
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Checkmate’s Digital Menu Boards
Checkmate’s digital menu boards help restaurants increase average check size by surfacing the right add-ons and offers at the right moment. In a recent 30-day test with a national QSR brand, average check size increased by nearly $1 per order, about a 6% lift, with no extra labor and no slower lines.
Learn more at https://www.itsacheckmate.com
