Digitalization and digital transformation have been an important topic for a lot of industries and application domains during the last years. In many enterprises, the result is a long list of digitalization projects – some of them completed, many still ongoing - and doubts about long-term benefits. Where are the disruptive effects of digital transformation? Radical digitalization is a way of (re-)focusing on innovation opportunities with strategic and long-term effects for an enterprise. In practice, this requires definition of problems and goals, changes in business models, design of new processes and services – and much more that can be supported by enterprise modeling. The resulting challenges and opportunities for enterprise modeling are discussed in the paper. The perspective taken is the practice of enterprise modeling rather than new theoretical approaches.