For several decades, maturity models have been regarded as a magic bullet for enterprises’ economic growth processes. In these models, domains are structured and divided into (mostly linear) levels that are used as benchmarks for enterprise development. However, this approach has its shortcomings in the context of complex topics like digitalization. As we understand it, digitalization defines a conceptual approach to a phenomenon that is individually important and promising in different ways for different enterprises. Consequently, existing maturity models in their current form are not able to reproduce the full extent of digitalization for enterprises, as the models are too general—especially for SMEs of different sizes and from different sectors. In our research, we propose a maturity model approach that introduces the concept of roles as a possibility to depict enterprises’ specific components, which are then added to a static core model. By doing so, the resulting maturity model is more flexible and scalable for SMEs’ specific needs. Furthermore, we introduce a new assessment approach for defining whether improving digitalization is truly relevant and worthwhile for the enterprise.