In research, industrial case studies are a possibility to collect information about complex phenomena from the environment where they occur. Digital transformation (DT) is a complex phenomenon, but there is a paucity of published case studies which describe the intermediary steps taken in enterprise DT activities. The paper contributes to a more diversified picture of digital transformation (DT) by describing and analyzing the step-by-step transformation of five case studies. The approach proposed for planning and analysis of DT cases in small and medium-sized enterprises (SME) consists of three elements: (a) focus on the dimensions “products/services” and “operations” when initiating DT in SME, (b) use step-by-step transformation along transformation paths instead of aiming at transformation in one go, and (c) include the success factors of DT known from literature in the step-by-step approach.