Celebrity investors pile into consumer savings startup Checkmate

We’ve all been there. Shopping online and desperately searching for a promo code so that you can save some money on a purchase.

Well, at least I’ve been there.

Enter Checkmate

The startup wants to make those days of promo/discount/coupon code hunting a thing of the past. And it’s just raised another $15 million in Series A funding to help make that happen.

A few things about this raise caught our eye. For one, Checkmate just announced a $5 million seed raise last September. The days of raising capital so soon after another round is not nearly as common as it used to be. Secondly, the company’s apparent rapid growth. 

It hit No. 1 in the Apple App Store at the end of last year and is today announcing it has surpassed over 400,000 users, including 60,000 daily active users. Checkmate also boasts 600,000 followers across its TikTok and Instagram accounts. 

And thirdly, the breadth of its investor base is notable. Google Ventures (GV) led its latest round, which also included participation from Mantis VC (The Chainsmokers’ venture firm), Wischoff Ventures, BDuck Capital and Saurabh Gupta, partner at DST Global. Angel investors include Paris Hilton, as well as CEOs, current and former founders and executives from Honey, Pinterest, Ancestry.com, Rakuten, Google, Grindr, Amazon, Linktree and Brex.   

So just what does Checkmate do that has so many people paying attention?

It has built a free iPhone app — that it says “pulls all your shopping into one place, tracks your packages and saves you money on 40,000 online stores.” The company is betting on the fact that most of us ignore marketing emails because many end up being filtered into a “promotions” folder. It’s also wanting to relieve shoppers of frequent promotional text messages that can get tuned out or opted out of.

Once you install the app, you can shop online and Checkmate will pull all the available discounts in place. It claims to find codes online, extract codes from email and also partners “exclusively” with some brands on new codes — claiming to save users “2x more than the competition.” 

The app leverages the Safari mobile browser via an extension. The company says this is key because not only are more people shopping online, they are using their phones to do so. It goes a step further by offering live order updates, package tracking and notifications of new sales and is available on desktop, too.

GV partner Frederique Dame believes that Checkmate’s “viral growth over the past eight months demonstrates early product-market fit.”

She said in a statement: “The last decade has seen a boom in e-commerce, but our shopping experience hasn’t changed until now. We strongly believe in Checkmate’s technology, team, and approach to reaching new consumer audiences.”

Australian-born Harry Dixon, Rory Garton-Smith and Elliot Rampono started Checkmate in late 2021, combining an interesting mix of backgrounds. Dixon (CEO) once worked with famed architect Frank Geary, and Garton-Smith (CTO) spent two years as an engineering project manager at Apple, working on the iPhone.

Looking ahead, the trio have big plans. They say they want to create “a personalized end-to-end shopping experience,” or a personalized shopping assistant.

They say: “As we evolve, we believe the entire shopper experience should be personalized based on shopping habits and interests, so that shoppers feel like recommendations are helpful rather than the endless spam they’re familiar with.”

The company makes money through an affiliate model. It takes a percentage of purchase after driving traffic to a particular retailer, which can range anywhere from 1% to 7% depending on the retailer and the item.  

Says Garton-Smith: “We fundamentally think there’s an opportunity to reinvent online store marketing…We would love, like two years from now — if you want to run a marketing campaign, and you’re a big online store, you go through Checkmate. We want to be the marketing platform, as opposed to just helping them surface their existing efforts.”