The demands on the competitiveness of original equipment manufacturers (OEMs) are increasing due to the global economic situation, fluctuating production volumes, and the possibilities offered by digitalization technologies. The transformation of companies from the legacy world to a cloud-based, service-oriented environment is essential for maintaining their market position and stable operations. This master thesis answers to the challenges of the beforementioned transformation are given based on the business case "Replacement of assembly flag". First, the assembly flag process is described in terms of processes and technology. Further, the path from an IT monolith to a cloud-based service-oriented system landscape is shown. This is followed by transformation descriptions in the areas of technology, process, competence and criticality which concretize and enable the transition from the legacy world to the cloud world. After a component of the legacy world has been transferred to a cloud application this is evaluated in terms of cost. In this course, a "blueprint" for cost estimates and comparisons for future cloud applications is presented. In addition to this evaluation, the non-monetary value contributions of the cloud service are also measured by key performance indicators which are mapped in an IT balanced scorecard. Finally, a novel service-oriented rollout strategy for future cloud applications is recommended that leverages the agile project approach's advantages, such as flexibility and responsiveness.