The importance of digitalization continues to grow, with companies from all sectors and of various sizes subject to this influence. To remain competitive in the future, companies must recognize and overcome the opportunities and challenges of digitalization in the long term. To do this, companies can develop an entire digitization strategy that affects all areas of the business, enabling them to achieve a holistic digital transformation and ensure their survival in the digital age. Based on a qualitative–empirical research design, this study examines whether small and medium-sized enterprises (SMEs) and large enterprises (LSEs) have such a strategy, and how it is structured. In particular, it addresses the use of new technology, changes in value added, structural changes and the financing of digitalization. At the same time, there is an examination of any similarities and differences among the different company sizes.