Fintech · New York City, United States · Founded 2008
ShopKeep, now known as ShopKeep by Lightspeed, was established in 2008 and is headquartered in New York City. The company originated from the firsthand frustrations of its founder, retailer Jason Richelson, who, along with Amy Bennett, sought to replace the cumbersome and unreliable point-of-sale (POS) systems prevalent in his own stores. Richelson's experience as a wine store owner in Brooklyn directly informed the creation of a simpler, cloud-based POS solution after his own system crashed one too many times. David Olk later joined as a third co-founder to help secure outside capital. The company's trajectory was significantly influenced by the launch of the Apple iPad in 2010, which ShopKeep adopted as an affordable hardware base for its system, a departure from the expensive traditional POS terminals.
The firm provides a cloud-based point-of-sale system primarily for small and medium-sized businesses within the retail and hospitality sectors, including retail shops, coffee shops, restaurants, and bars across the United States and Canada. Revenue is generated through monthly or annual subscription fees for its software, which is offered in tiered plans with varying feature sets. The business model also includes integrated payment processing through Lightspeed Payments and financing options via ShopKeep Capital.
The core offering is a POS system that operates on iPads and Android tablets, enabling merchants to manage sales, process various payment types (including credit cards and contactless payments), manage inventory, handle employee time tracking, and access real-time sales reports through a web-based "BackOffice" portal. Key features include inventory and customer management, employee controls, and detailed analytics. The platform was designed with an intuitive user interface to be easily operated by cashiers and managed remotely by business owners. A significant milestone in the company's history was its acquisition by Lightspeed in November 2020 for approximately $440 million, integrating ShopKeep into a larger global commerce platform. At the time of the acquisition, ShopKeep was serving over 20,000 customer locations and generated roughly $50 million in annual revenue with a gross transaction volume of approximately $7 billion.
Keywords: point of sale, POS system, iPad POS, retail management, restaurant POS, small business POS, cloud-based POS, inventory management, payment processing, employee management, customer relationship management, sales analytics, BackOffice, mobile POS, Lightspeed, retail technology, hospitality technology, subscription software, credit card processing, business operations
Dealroom maps ShopKeep's team person by person — pinpointing the standout operators and scoring them across the six dimensions investors underwrite. The counts and shape below are a public preview; the named individuals and exact scores live in the platform.
51team members profilednamed & role-tagged by Dealroom
Source: Dealroom Talent Intelligence. Public profiles show counts and the team's shape only — request a demo for the named individuals, per-person seniority and tenure, and team benchmarks vs peers.
Market sentiment
What the market is saying about ShopKeep
An AI-synthesized read of the highest-engagement posts about ShopKeep on X over the past 7 days. We rank by likes & retweets, ignore corporate channels, and surface the themes that broke out from real people.
Reading the room on X — pulling top posts and synthesizing themes…
Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour
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