Since the early 2000s, increasing digitalization across various economic sectors has led to the growth of the field of e-Business. Currently, artificial intelligence (AI) technologies have been increasingly integrated into various sectors, often reshaping the way workflows have been conducted. In the field of e-Business, AI technologies have a wide range of applications, within domains such as marketing, supply chain management, fraud detection, customer interaction, and process automation. In this research paper, a case study is conducted on South African retail group Shoprite Holdings and its use of AI in e-Commerce and broader e-Business is conducted. The various AI techniques used within different areas of the business’s operations are identified, and the factors influencing the business’s use of AI are investigated through the application of the PESTEL framework. It is found that legal and economic factors are the most salient when considering the group’s use of AI, and the importance of interpreting the results within a local legal and economic context is emphasized. Recommendations are provided on potential future AI applications on the part of the business.