checkmate founders rory elliot and harry

Investment Notes: Checkmate

Date Published:
September 29, 2022

We’ve recently co-led the Seed round in Checkmate, a platform unifying the e-commerce experience. We have great belief in Checkmate’s ambition and its founders and we wanted to share why.

Rebundling of e-commerce

At Blackbird, we have been gnawing on a “river of inquiry” for the future of e-commerce for some time. E-commerce penetration is growing, shopping is becoming more social- and mobile-driven, brands are seeking deeper and cheaper customer relationships, and consumer experience expectations are higher than ever before. These themes have guided our investments into Carted, Eucalyptus, Instant, and Lexer… and now, Checkmate.

Despite its growth, e-commerce remains a largely fragmented experience. There are multiple platforms, discovery is poor, keeping track of information is hard (orders, shipments, discount codes), email and SMS overwhelm is real, personalisation is weak, and consumer marketing is increasingly ineffective.

Checkmate is building a personalised “smart shopping” tool - a product that unifies a consumer’s entire e-commerce experience - from discovering brands, applying savings, and managing orders and shipping - into a delightful UX. 

Checkmate’s dashboard experience
“What is this wizardry?”

Checkmate’s first MVP product is live, available as both a mobile app and browser extension. You can download the iOS mobile app here and the Chrome browser extension here now!

Checkmate seamlessly integrates with your email inbox to deliver you a beautiful, unified shopping experience. Three core features today include:

  1. Loyalty and discount codes - stores your loyalty programs, gift cards, and discount codes (scraped from email and the internet) and uses native browser extensions to ensure maximum savings are applied automatically for you at retailer checkouts. This is the primary focus of today’s product
  2. Order history - profiles your past and present orders, profiling 10,000 stores and growing.
  3. Shipment tracking -  tracks your shipments with real-time alerts so you know exactly when packages will arrive at your doorstep.
Checkmate’s savings browser extension

Checkmate’s product delivers a spellbindingly beautiful user experience, with users currently saving on average US$35 per order. Most importantly, customers love it:

“What is this wizardry - $320 saving on an $800 basket”

“This put such a big smile on my face when it popped up”

A trojan horse

Some of the best businesses are built as “trojan horses” - where the core business is a beachhead to something much greater. For Carta, their core equity management business was a trojan horse for their secondary marketplace (CartaX). And it is Checkmate’s second act that gets us most excited. 

In future, Checkmate will function as a powerful engine for brands to reach hyper-targeted audiences and build strategic, long-term relationships. Checkmate’s “Act 1” consumer product helps them gather rich data on a mass user base, which is their trojan horse for an “Act 2” where they own the top of the funnel - product discovery. Checkmate plans to launch additional features including:

  1. Product discovery - by intimately understanding all of a consumer’s purchases, Checkmate can uniquely profile them and deliver personalised recommendations.
  2. Wishlisting - a tool that allows users to easily “wishlist” their favourite items.
  3. B2B retailer marketing - Checkmate’s unique shopper insights supports hyper-targeted retailer marketing. For example, if Checkmate knows that you buy Nike runners, they can support a custom Adidas promotion. Or if Checkmate knows that you cart-abandoned a new pair of Ray-Bans, they can send over a coupon a few days later.

Merchants crave consumer insights and Checkmate can uniquely deliver them. Executing on this Act 2 is how Checkmate becomes a generational company.

Three mates from Perth
Checkmate cofounders: Rory Garton-Smith (L), Elliot Rampono (M), and Harry Dixon (R)

Harry, Rory and Elliot grew up as mates in Perth. They marry complementary skills and epitomise the “hungry not the proven”. Harry is an elite operator with a deep background in e-commerce, sales, and partnerships. He was formerly at EasyPost, where his revenue figures matched the next seven best salespeople combined. Rory is a product-obsessed engineer who was formerly on the Apple iPhone engineering team. And Elliot is a top developer with a beautiful sense of product.

They execute with speed. In just a few months, they have launched a browser extension and mobile app, launched a beta and then a MVP, developed a spellbinding roadmap, and pulled together an impressive US$5M seed round. 

We are incredibly excited to welcome Checkmate to the Blackbird family, and to be supporting them on this journey. 

And… as a reminder, you can download the iOS mobile app here and the Chrome browser extension here!

Tom and Max, on behalf of Blackbird.