The software that quietly pipes DoorDash and Uber Eats orders straight into 23,000+ restaurant kitchens.
Every time a restaurant adds a delivery app, it usually adds a tablet, a login and a fresh way to key an order in wrong. Checkmate's entire reason to exist is to delete that mess. The New York company, legally ItsACheckmate.com Inc., sits between the ordering channels a restaurant sells through and the point-of-sale system it runs on - taking an order placed on DoorDash, Uber Eats or a brand's own website and dropping it directly into the POS, no re-typing required.
That plumbing sounds mundane until you watch a Friday dinner rush. Orders arrive from a half-dozen platforms at once, each with its own device and its own menu. Checkmate consolidates them into a single flow and, just as importantly, lets an operator manage every menu from one dashboard. Change a price once and it propagates across the channels - the kind of unglamorous synchronization problem that costs restaurants real money when it breaks.
Since 2016 the company has expanded outward from that core. It now spans first-party web and app ordering, self-service kiosks, catering, loyalty and marketing tools, accounting reconciliation, and - most recently - voice AI that answers the phone and works the drive-thru. The company describes its approach as a blend of technology and hands-on human support, aimed at letting restaurants scale their digital operations with minimal effort.
Checkmate began with a familiar annoyance. Founder Vishal Agarwal was at an airport restaurant in San Francisco with a flight boarding and no server in sight to bring his check. Most people grumble and make the gate. Agarwal - who earned his MBA in India and spent four years at Citigroup before turning to startups - started sketching a way to pay and split a bill from a phone.
The early idea was faster checkout; the durable business turned out to be integration. As third-party delivery exploded, every restaurant became a multi-channel operation whether it wanted to or not, and the hard part shifted to keeping all those channels connected and accurate. Checkmate leaned into that. It built from the one system that absolutely cannot be wrong - the POS - and worked outward toward the customer-facing edges.
That expertise is now stacked deep: 130+ ordering integrations, 50+ POS integrations, and a decade of operating experience with enterprise brands whose margins live and die on order accuracy. In 2022 the company opened an India subsidiary to scale its engineering and operations.
Checkmate has added roughly one major product layer a year. No single leap looks dramatic; stacked over a decade, it's a platform.
Routes DoorDash, Uber Eats, Grubhub and more directly into the POS - no tablets, no manual re-entry.
One dashboard to sync prices, items and availability across 130+ platforms in real time.
Custom-branded first-party ordering so restaurants own the customer relationship and the data.
Accounting tool that tracks payouts, fees, refunds and disputes across every delivery channel.
In-store ordering kiosks running on the same POS and menu backbone.
AI phone and drive-thru ordering that answers calls, takes orders and upsells automatically.
Reported figures across company statements and trade press. Order totals are cumulative and approximate.
Who uses it. Checkmate serves enterprise and multi-unit restaurant brands alongside independent operators. Its customer base is reported to include brands associated with Inspire Brands - Arby's, Sonic and Buffalo Wild Wings - as well as Wendy's, plus thousands of smaller restaurants running the same integration and menu tools.
The problem it solves. Channel sprawl. A restaurant selling on six platforms faces six devices, six menus and six places to make a costly mistake. Checkmate collapses that into a single connected system with one source of truth for the menu.
How it's different. Where some rivals lead with a marketing storefront, Checkmate built integration-first, starting at the POS. Its depth of POS coverage and its willingness to do hands-on support - not just ship software - is the pitch. When your customer's parent company (Inspire Brands) also becomes your investor, replacement gets structurally harder.
The alternatives. It competes with Olo, Deliverect, Otter, Chowly and Qu, among other restaurant ordering and integration platforms.
Checkmate is a B2B SaaS company. Restaurants and enterprise brands pay recurring subscription and per-transaction or per-integration fees to connect their ordering channels to the POS and to run first-party ordering, kiosks, voice AI, reconciliation, loyalty and menu management. According to the company, the core POS-integration business is already profitable - a notable detail, given it raised fresh capital anyway.
That is the strategic tell. When the 2024 Series B closed, Checkmate did not need the money to survive; it directed the funds toward product - voice AI and kiosks aimed at the mid-market and enterprise segments - rather than runway. Within the broader restaurant technology market, Checkmate occupies the integration and digital-ordering layer: the infrastructure connecting delivery demand to kitchen operations, sitting beneath the consumer apps and above the POS.
Vishal Agarwal starts ItsACheckmate.com to route third-party orders into restaurant POS systems.
Raises Series A funding and passes one million orders processed.
Arby's parent Inspire Brands backs the company in a Series B round.
The platform crosses 100 million orders processed.
Opens an India subsidiary to scale engineering and operations.
Launches the Reconcile accounting tool and acquires Open:Tender.
Ships self-service kiosks and raises a $10M Series B led by Tiger Global.
Rolls out AI-powered digital menu boards, extending its in-store line.
Roughly $13.25M raised in total, per data providers. Earlier round amounts were not publicly disclosed.
| Round | Amount | Date | Notable Investors |
|---|---|---|---|
| Series A | Undisclosed | 2018 | Undisclosed |
| Series B (Inspire round) | Undisclosed | 2020 | Inspire Brands |
| Series B | $10,000,000 | Oct 2024 | Tiger Global, Kitchen Fund, Continental Grain Co., Inspire Brands |
Podcasts and features with founder Vishal Agarwal and product walkthroughs from the Checkmate team.
Checkmate connects restaurants' digital ordering channels - third-party delivery apps, first-party web and app, kiosks and voice AI - directly into their point-of-sale system, and lets them manage menus across all channels from one dashboard.
Vishal Agarwal founded ItsACheckmate.com Inc. in 2016, based in New York. He earned his MBA in India and spent four years at Citigroup before starting the company.
Roughly $13.25M total, including a $10M Series B led by Tiger Global in October 2024, with participation from Kitchen Fund, Continental Grain Company and Inspire Brands.
Checkmate reports more than 23,000 live restaurant locations and 130+ ordering integrations, serving enterprise brands and independent operators alike.
It competes with restaurant ordering and integration platforms such as Olo, Deliverect, Otter, Chowly and Qu.