Book excerpt: Remaining competitive in the retail industry of South Africa in the digital age is a major business concern. In the age of „digital natives”, people are well-connected on various digital technology platforms and are digital consumers. Digital technologies offer retail organizations new innovative ways to create value by utilizing digital business strategies, processes, and products. This qualitative research study explores the perception of retail strategy experts and decision-makers toward realignment of IT and business strategies considering digital transformation in South Africa. Based on interviews with seven managers and decision-makers in the retail industry, the study reveals that digital technologies have disrupted traditional ways of doing business. The study proposes eight major recommendations, in which retail traders could innovate their business strategy to enhance value creation beyond traditional approaches to retailing. It provides a good starting point for academic research in a domain that is deficient in theoretical and empirical research on the South Africa retail sector, and offers retailing managers a conceptual model to guide them toward a digital business strategy for transient competitive advantages.