This guest editorial presents the special section of 14th IFIP WG 8.1 Working Conference on the Practice of Enterprise Modeling (PoEM 2021). The best papers of PoEM 2021 were invited to be revised and significantly expanded. Eight papers were finally accepted for publication in the special section. These papers are an excellent representation of the state of the art on Enterprise Modeling, showing as well the importance of applying the research contributions into practice.