Enterprise Architecture is the process of translating business vision into strategy. Hence, Enterprise Modeling is the process of translating an organization’s strategic intent into mandated socio-technological innovation projects required to reach an agreed future state of the firm’s operation.This paper uses four longitudinal case studies at DHL Express Europe to introduce a significant paradigm shift to modeling of the enterprise at the work system level as an abstract representation of the desired future state of the enterprise. This representation specifies in full the business capabilities serving current and future customer needs and the work system configuration enhancements needed to satisfy the customer needs. The associated project has four p steps: (1) Assessment of Status Quo, (2) Agreeing on the desired End-State, (3) Evolution of legacy work-systems, (4) Removal of Obsolete components. This process model explicitly includes the necessity to search for, address and remove all strategic, financial, operational and technical legacy issues identified during the baseline of the status quo. Enterprise Architects should be embedded in each implementation project for Project Assurance purposes in order to monitor the delivery of the agreed end-state.