In a complex business environment, the quest for intelligent solutions has placed artificial intelligence (AI) at the center of many operational business decisions, particularly within the retail sector. As retailers’ investment in AI disrupts value chains, they must adapt to organizational changes, yet limited research exists on how to address organizational challenges when integrating AI into the retail value chain. Using 23 expert interviews with retail executives and AI vendors, this study investigates the socio-technical challenges retailers encounter when integrating AI into their value chain and offers strategies to address these organizational hurdles. We identify micro-, meso-, and macro-level factors impacting AI implementation in retail and propose an AI Implementation Compass to address the change management process. This framework serves as a guide to navigate the complex landscape of AI adoption, emphasizing a holistic approach that considers not only internal organizational dynamics, but also external market forces.