Checkmate

Checkmate

Personalized deals and order tracking platform

Overview

Checkmate is a free online shopping platform that delivers personalized deals from brands and centralizes order tracking. It uses a Chrome extension on desktop and an iPhone app on mobile to surface deal recommendations and order updates when shoppers need them, helping users save time and find better prices. The service aggregates promotions and order information across brands and presents it in one place, and it also offers a package-tracking feature so users can monitor deliveries without visiting multiple sites. Its revenue likely comes from affiliate marketing, earning commissions on purchases made through the platform. Compared with competitors, Checkmate combines personalized deal discovery with a unified order-tracking hub in a single, free-to-use product, accessible across desktop and mobile. The goal is to simplify and accelerate online shopping by delivering relevant deals and centralized order information to consumers.

About Checkmate

Simplify's Rating
Why Checkmate is rated
C-
Rated C on Competitive Edge
Rated C on Growth Potential
Rated D+ on Differentiation

Industries

Data & Analytics

Consumer Software

AI & Machine Learning

Company Size

51-200

Company Stage

Series B

Total Funding

$30M

Headquarters

San Francisco, California

Founded

2020

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Simplify's Take

What believers are saying

  • 1 million users across iOS and Chrome drive viral growth.
  • Network reaches 100M US shoppers and 400 premium brands.
  • $100M saved boosts retention and weekly spending volume.

What critics are saying

  • Honey erodes 1M users with 20M scale in 6-12 months.
  • Apple ATT slashes personalization accuracy by 40-60% now.
  • Google Shopping AI obsoletes Chrome extension in 12 months.

What makes Checkmate unique

  • AI generates personalized deals from emails and web at checkout.
  • Supports 500,000 stores with automatic coupon application.
  • Tracks orders and stores gift cards in unified dashboard.

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Funding

Total Funding

$30M

Below

Industry Average

Funded Over

3 Rounds

Notable Investors:
Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Below Average

Industry standards

$35M
$30M
Patreon
$45M
Linktree
$65M
Substack
$100M
ClickUp

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

-1%

2 year growth

-5%
Networld Media Group
Oct 23rd, 2024
Checkmate raises $10M in Series B for restaurant voice AI, kiosk solutions

Checkmate has raised $10 million in a Series B funding round, led by Tiger Global, which aims to scale adoption of Checkmate's restaurant voice AI and kiosk solutions.

Startup Daily
May 26th, 2023
The Chainsmokers, Paris Hilton pile into $23 million Series A for expat Australian online shopping startup

Paris Hilton and electronica duo The Chainsmokers have been added to the A-lister cap table of LA-based expat Australian startup Checkmate, which has raised US$15 million (A$23m) in a Series A.

FinSMEs
May 25th, 2023
Checkmate Raises $15M In Series A Funding

Checkmate, a Los Angeles, CA-based automated savings platform for modern online shopping, raised $15M in Series A funding. The round was led by GV (Google Ventures), with support from Mantis VC (The Chainsmokers), Common Metal, BDuck Capital, Black Angels Group, Wischoff Ventures, Fuel Capital, Blackbird Ventures, F7 Ventures, Night Capital, Scribble Ventures, Paris Hilton, Cart Reum (M13 Ventures), Saurabh Gupta (Partner at DST Global), Tim Kendall (Meta Pinterest), Jeff Boneforte (exGrindr Yahoo), James Chin Moody and Geraldine Chin Moody (Sendle), Alex Zaccaria and Anthony Zaccaria (LinkTree), Trevor Neff (Ashton Kutchers Sound Ventures), Arthur Levy and Michael Tannenbaum (Brex).    The company intends to use the funds to expand operations and its business reach.Led by CEO Harry Dixon, Checkmate finds the best deals from an email and across the web and applies them at checkout. It also track all package shipments in a dashboard and store gift cards in a digital wallet. The phone app leverages the Safari Mobile Browser via an extension plugging into it to automatically provide users savings while they shop at 40,000 stores. Checkmate finds codes online, extracts codes from email, and partners exclusively with brands on new codes. FinSMEs25/05/2023

GV
May 25th, 2023
Checkmate: A Breakthrough in Digital Shopping

Last September, Checkmate launched a mobile savings app and browser extension to create a breakthrough in digital shopping.

Business Wire
Sep 26th, 2022
Checkmate Announces $5 Million Seed Funding Round, Led By Fuel Capital

SAN FRANCISCO--(BUSINESS WIRE)--Checkmate, a personalized smart shopping tool that makes it easy for users to discover brands, apply savings and manage their orders post-purchase, today announced it has secured a $5 million seed funding round led by Fuel Capital. Checkmate will use the new investment to accelerate its product development and customer growth. Other participants in the round include Kevin Johnson, former CEO of Ebates at Rakuten; f7 Ventures; Blackbird Ventures; Scribble Ventures; Hyper; and Susa Ventures. Consumers typically are so inundated with personalized email deals from brands that it’s tough to manage them all and remember to apply each deal at checkout. Available as both a mobile app/extension and laptop extension, Checkmate is the first solution that gathers all the best deals from a user’s personal email and the web and automatically applies them at checkout to help smart shoppers save the most they can

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