Artificial Intelligence (AI) was perceived as the future of industries. The adoption of AI was put in place as the industry movement towards technology advancement. Retailer business, dealing with customers, shoppers, products, and supply chain process, opened up opportunity for business improvement using the AI. Starting with the increasing awareness of data importance, implementation of AI expectedly would elevate the conservative retail business by incorporating machine learning into the business process. However, the development of artificial intelligence in retail did not see a firm road map yet. This led to retailer industry being behind in terms of AI adoption when compared to other industries. The objective of this research was to asses and analyze the stages of AI implementation in retailer in Indonesia, in order to build road map of the implementation. Data was collected primarily using case study in one of the retailers. Reference was taken from previous studies and journals discussing the related subjects. The study used qualitative methodology, in which in depth interviews with the subject matter experts of the respective retailer conducted in explorative way. Findings highlighted the limited preparation to adopt AI in the case study retailer. There were to drivers for this. First was unformulated digital transformation strategy and second was competitive strategy that led to business initiative priority. The limited preparation led to road map designed had to begin from building strong understanding of both AI and organizational capabilities as fundamental stepping stone. Top leadership involvement became crucial to drive top down direction regarding AI implementation strategy.