Today’s dynamic business environment requires enterprises to be agile in order to remain competitive. Competition also impacts enterprise modeling (EM) aiming at the systematic development of the enterprise’s business processes, organizational structures, and information systems. Although EM is a mature discipline, organizations still do not exploit the full potential of EM. We suggest, the concept of a Digital Twin of an Organization (DTO) provides a means of digitalization to introduce more agility. A DTO draws upon graph-based, machine readable knowledge representation of enterprise models. In order to run through various scenarios in real time, the DTO approach makes use of Context Spaces that provide the required information semantically structured, which improves the comprehensibility and applicability of the used models. The DTO combines EM with operational reality and, thus, increases the agility of the enterprise.