Fundraising Fox

Checkmate

San Francisco, US · 19 known investors

Checkmate generates exclusive discount codes with partner brands and automatically finds the best prices across 200,000+ retail stores for shoppers. The app aggregates deals for beauty, apparel, home goods, and other consumer categories from household names and niche brands.

Also known as Checkmate · joincheckmate

Founders & leadership

HDHarry Dixon
Harry DixoninFounderFounder of Checkmate, a shopping app that sources exclusive discount codes with partner brands and compares prices across retailers. He is also building mate., an AI marketing tool that identifies in-market shoppers and runs revenue-focused campaigns through the Checkmate ad network, used by brands including Everlane, No Bull, Brooklinen, and Summer Fridays.
RG
Rory Garton-SmithFounder

Investors · 19

Also in the syndicate · 14

Alex ZaccariaAnthony ZaccariaArthur LevyBDuck CapitalBlack Angels GroupCarter ReumCommon MetalGeraldine Chin MoodyJames Chin MoodyJeff BonforteMichael TannenbaumSaurabh GuptaTim KendallTrevor Neff

Funding

SEC filings, press & company announcements

$10M disclosed across 1 of 3 rounds · 2022–2024

Source: company announcements and press reports — follow each round's link for the claim.

Company profile

researched Aug 2026

Checkmate is a consumer e-commerce savings product delivered as a mobile app and browser extension. The company says it does not only surface existing discount codes but also generates exclusive codes with partner brands, while automatically checking for the best available price across more than 200,000 stores. It is distributed as a free Chrome extension and iOS and Android apps, and originally leveraged the Safari mobile browser via an extension, which the company positioned as important because a large share of shopping occurs on phones [0][1][6].

At the time of its 2023 Series A, Checkmate described a product that finds codes online, extracts codes from a user's email inbox, and partners exclusively with brands on new codes, claiming average savings of 2x competing tools across roughly 40,000 supported stores. Adjacent features include package tracking and live order updates, consolidated shopping information, wishlists, and a gift-card wallet [3][5][6][7]. The company's stated ambition is a personalized end-to-end shopping assistant covering browsing, buying and delivery, and eventually a marketing platform through which online stores would run campaigns rather than merely surfacing existing promotions [5][6].

A separate Checkmate FAQ site describes business-facing products named Enrichment, Targeting and Audiences along with brand case studies, indicating a merchant-side offering alongside the consumer app [2].

Founding story

According to TechCrunch, Australian-born Harry Dixon, Rory Garton-Smith and Elliot Rampono started Checkmate in late 2021. Dixon serves as CEO and previously worked with architect Frank Gehry; Garton-Smith is CTO and spent two years as an engineering project manager at Apple working on the iPhone [6]. Blackbird identifies the same three individuals as co-founders [7].

Business model

Checkmate is free to consumers and monetizes through an affiliate model, taking a percentage of purchases after driving traffic to a retailer, ranging from roughly 1% to 7% depending on the retailer and item [6]. It also establishes exclusive code partnerships directly with brands [0][1][5], and its FAQ site references merchant-facing Enrichment, Targeting and Audiences products [2].

Affiliate commissions of approximately 1%–7% of purchase value paid by retailers for traffic and conversions driven through Checkmate [6].

Traction

As of the May 2023 Series A, Checkmate reported over 400,000 users and 60,000 daily active users (the company's own press release cited 380,000 users and 55,000 daily active users), 600,000 social followers, coverage of about 40,000 stores, a No. 1 Apple App Store ranking at the end of 2022, and millions of dollars spent through its extension weekly [5][6]. The current website states 2M+ shoppers, 200,000+ brands and a 4.8 App Store rating from tens of thousands of reviews, while its login page claims over 50M+ shoppers in its network and 500k online stores [0][1][4].

Latest developments

The most recent third-party reporting in these sources is the May–June 2023 Series A. The company's current website shows an expanded product footprint — a free Chrome extension plus iOS and Android apps, 2M+ shoppers, 200,000+ brands and a 4.8 App Store rating — and a positioning around generating exclusive codes with partner brands [0][1]. A separate Checkmate FAQ domain lists business products called Enrichment, Targeting and Audiences with brand case studies [2]. Blackbird still lists Checkmate as a portfolio company at seed stage, invested 2022 [7].

Full profile — market position, technology, go-to-market, geography, history, risks & controversies

Market position

Checkmate positions itself against existing savings extensions and coupon apps, arguing that they access only a small share of available savings as retailers shift to personalized, individually targeted offers; the company claims average savings of 2x competitors [5][6]. Investors and press cited rapid viral growth and an early No. 1 Apple App Store ranking as evidence of product-market fit [5][6]. Its angel investor base includes executives from Honey, Rakuten, Pinterest, Ancestry.com, Google, Grindr, Amazon, Linktree and Brex [6].

Checkmate frames its differentiator as generating codes rather than only finding them: exclusive codes created with partner brands, combined with automated price checking across a large store network, email code extraction, and adjacent utilities such as package tracking, wishlists and a gift-card wallet [0][1][3][5][6][7].

Technology

Checkmate combines automated code discovery online, extraction of codes from users' email, and exclusive codes negotiated with partner brands, applied automatically at checkout [5][6][7]. The product originally operated as an iPhone app using a Safari mobile browser extension and later expanded to desktop, Chrome, iOS and Android [0][1][6]. The company's help center and login page refer to "savings AI," and its site describes automatically generated, user-specific codes [0][3][4].

Go-to-market

Free consumer distribution via the Apple App Store, Android and a Chrome browser extension, amplified by viral social media content; at the Series A the company reported over 600,000 followers across TikTok and Instagram, and its site displays individual videos with millions of views under the @joincheckmate and @checkmatesavings handles [0][1][5][6]. On the supply side, Checkmate signs exclusive code partnerships with brands [0][1][5].

Online shoppers seeking discounts at checkout, particularly mobile users, plus consumer brands and online retailers that partner with Checkmate on exclusive codes and merchant-facing products [0][1][2][5][6].

Geography

The founders are Australian-born and the company is backed by Australian firm Blackbird Ventures [6][7]; the sources do not specify headquarters or operating markets beyond online distribution through the Apple App Store, Android and Chrome [0][1].

History

Checkmate was started in late 2021 [6]. Blackbird invested in 2022 and states it co-led the company's seed round [7]; TechCrunch notes a $5 million seed raise announced in September 2022 [6]. The app reached No. 1 in the Apple App Store at the end of 2022 [5][6]. In May 2023 the company announced a $15 million Series A led by GV, reporting more than 400,000 users and 60,000 daily active users at roughly eight months of consumer traction, across about 40,000 supported stores [5][6]. The current website reflects a substantially larger stated footprint of 2M+ shoppers and 200,000+ brands, with distribution via Chrome, iOS and Android [0][1].

Risks & controversies

Publicly reported user and coverage figures vary across sources and time: the company's own press release cited 380K users, 55K daily actives and 40,000 stores, while contemporaneous TechCrunch reporting cited 400K users and 60K daily actives [5][6]; the current website cites 2M+ shoppers and 200k+ brands while its login page cites 50M+ shoppers in network and 500k stores, an inconsistency across company-controlled pages [0][1][4]. TechCrunch also noted the unusually short interval between the September 2022 seed round and the May 2023 Series A [6]. The press release references new regulations making it harder for businesses to reach consumers, a factor affecting the sector [5].

Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.

Key figures

latest reported
Affiliate commission rate rangeMay 20231% to 7% of purchase value depending on retailer and item
App Store ratingJan 20264.8 stars
Brands/stores coveredJan 2026200,000 brands
Daily active usersJun 202355,000 users
Registered usersJun 2023380,000 users
ShoppersJan 20262,000,000 shoppers
Shoppers in network (login page claim)Jan 202650,000,000 shoppers
Social media followers (TikTok and Instagram combined)May 2023600,000 followers
Supported online storesMay 202340,000 stores

Company-reported or press-reported figures, each dated to when it was claimed — not independently audited.

Competitors · 2

by search overlap

Companies competing with Checkmate for the same Google search keywords, organic and paid, via search-intersection analysis.

Timeline · 3

launches, deals, and filings
May 2023
Checkmate raises $15M Series A led by GV

Checkmate announced a $15 million Series A round led by GV (Google Ventures), with participation from Mantis VC, Common Metal, BDuck Capital, Black Angels Group, Wischoff Ventures, Fuel Capital, Blackbird Ventures, F7 Ventures, Night Capital and Scribble Ventures, plus angels including Paris Hilton, Carter Reum, Saurabh Gupta (DST Global), Tim Kendall, Jeff Bonforte, James and Geraldine Chin Moody, Alex and Anthony Zaccaria, Trevor Neff, Arthur Levy and Michael Tannenbaum.

$15M source ↗

Sep 2022
Checkmate announces $5M seed round

TechCrunch reported that Checkmate had announced a $5 million seed raise in September 2022, roughly eight months before its Series A. Blackbird states it co-led the seed round and invested in 2022.

$5M source ↗

Jan 2022
Reached No. 1 in the Apple App Store

Checkmate hit the No. 1 position in the Apple App Store at the end of 2022, according to its Series A announcement and TechCrunch coverage.

source ↗

Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.

In the news

Research sources · 8

primary sources listed

8 public sources were cited for this profile; the first-party ones are listed here.

Frequently asked questions

What does Checkmate do?
Checkmate is a shopping savings app and browser extension that generates exclusive brand codes and finds best prices online.
Who founded Checkmate?
Checkmate was founded by Harry Dixon, Rory Garton-Smith.
Who are Checkmate's investors?
Checkmate's investors include Blackbird Ventures, Mantis Capital, Scribble Ventures, Tiger Global Management, Wischoff Ventures.
How much funding has Checkmate raised?
Checkmate has disclosed $10M raised across 1 of its 3 known rounds.
Where is Checkmate headquartered?
Checkmate is headquartered in San Francisco, US.