Automated checkout systems are on the rise—preferred by customers and businesses alike. However, most systems rely on the customer scanning one product at a time and identify the product using a barcode. This adds friction to the process. The Stockwell cabinet from 365 Retail Markets eliminates this friction by using visual AI to recognize items from a catalog. In this talk, we explain how the system works, the design decisions we faced, and the operational and technical challenges and opportunities in the “Visual AI for Retail” space. After a brief overview of the business space, we will delve into key technical aspects, including choice of camera and illumination, compute at the edge vs. the cloud, the AI inference pipeline and the data-labeling infrastructure for onboarding new products. We conclude with a look at collaboration opportunities in hardware, AI and data management.