The German engineering sector is one of the most prominent industries in Germany in terms of revenues, the number of employees, and reputation for the “Made in Germany” brand. In this industry, digital transformation (DT) has become a significant trend. DT is more than optimizing internal processes by digital means. It entails the offer of digital services and products and the enhancement of customer experience. Complex barriers need to be overcome to drive this transformation forward. Therefore, our study analysis the organizational barriers to DT within the German engineering industry. We follow a quantitative approach to gain insight on organizational barriers by a comparison of digitalized and less digitalized enterprises and their DTs. Our research demonstrates that digitalized enterprises perceive lower degrees of certain barriers in leadership, culture, employees, and skills, which are essential parts in a socio-technical view. However, there are still barriers that digitalized enterprises are struggling with.