ShopKeep has raised $137.0M in total across 5 funding rounds.
ShopKeep's investors include Floodgate, Founders Fund, Owl Ventures, Quotidian Ventures, RRE Ventures, Tribeca Venture Partners, Darrell Silver, Activant Capital, Alumni Ventures, American Express Ventures, Band of Angels, Declaration Partners.
ShopKeep is a cloud-based point-of-sale (POS) system originally designed for iPads and tablets, serving small businesses like retail shops, coffee shops, restaurants, and bars in the US and Canada.[2][1] It enables merchants to process sales, manage inventory, track customers, generate reports, and access real-time data remotely via a web-based BackOffice and smartphone app, solving the pain of outdated, crash-prone legacy POS systems with an intuitive, affordable cloud solution.[1][2] Acquired by Lightspeed in 2020 and rebranded as ShopKeep by Lightspeed (now fully integrated into Lightspeed POS S-Series), it supports over 23,000 locations with features like multi-location management, email receipts, and inventory triggers, showing strong growth from early adoption to enterprise-scale integration.[2][4]
ShopKeep was co-founded in fall 2008 by Jason Richelson, a Brooklyn retailer who experienced repeated crashes with his wine store's POS software, and Amy Bennett, out of frustration for a simpler solution tailored to small merchants.[2] Richelson, drawing from his retail expertise, envisioned a cloud-based system for anytime data access and intuitive interfaces; he hired Bill Walton as the original engineer to build it.[2] David Olk, ex-Director of M&A at IAC, joined as third co-founder and COO in 2011, enabling the first external funding round in December 2011.[2] Early traction built quickly, reaching nearly 2,000 merchants by 2012 across multiple locations, with features like iPad sales processing, cash drawer integration, and mobile inventory updates.[1]
ShopKeep rides the shift to mobile/cloud POS for SMBs, capitalizing on iPad proliferation and the need for affordable, always-on systems amid legacy hardware failures—perfect timing post-2008 recession when small retailers sought cost-effective tools.[1][2] It influences the ecosystem by democratizing advanced features like real-time analytics and omnichannel inventory (in-store, online, mobile) for non-tech-savvy users, paving the way for consolidations like Lightspeed's, which scales indie POS to enterprise retail tech.[2][4][3] Market forces favoring it include rising e-commerce integration demands and data-driven retail (e.g., customer insights, demand forecasting), positioning it strongly against fragmented competitors in a $10B+ POS market.[3]
As Lightspeed POS S-Series, ShopKeep's trajectory points to deeper omnichannel unification, AI-driven inventory forecasting, and expanded footwear/apparel verticals with compliance/security features.[3][4] Trends like mobile-first retail and unified commerce will propel growth, evolving its influence from SMB disruptor to integral Lightspeed backbone, sustaining momentum for merchants in a post-pandemic, hybrid sales world—echoing its origin as the reliable fix for crashed registers.[4][2]
ShopKeep has raised $137.0M across 5 funding rounds. Most recently, it raised $65.0M Series E in December 2018.
