The study of the transformation of retail chain stores (RCS) due to the impact of digitalization on them is a new problem. The main part of modern scientific research is devoted to separate directions of digitalization and does not consider conceptual aspects of these processes. The purpose of this article is to fill the existing research gap through the development of a new system concept of the digitalization impact on RCS transformations. The study shows the need to clarify the understanding of RCS strategic transformation caused by the drivers of different digitalization processes, which are not well understood today and are not taken into account when developing digitalization strategies. This situation has an extremely negative effect on the quality of RCS development and its competitiveness. The article consistently examines insufficiently covered problems in scientific literature and offers a new conceptual approach to the impact of digitalization on companies with regard to RCS transformation. New digitalization trends and their drivers have a deep impact on RCS transformations. A new system model is needed that integrates superdrivers and the impact of digitalization on the RCS transformation. Causal and heuristic forecasts of prospects, trends and results of digitalization, including contradictory results of AI development are included. We used materials from large retail chains “Magnit”, “Perekrestok” and “M.Video-Eldorado Group”. The research methods used were system modelling, cause and effect links building and heuristic forecasting based on logical models. The main results will be useful for researchers, managers, entrepreneurs and students in developing a clear understanding of digitalization development and its impacts, in order to better work out digitalization strategies and for the development of new directions of scientific research.