As business digitalization continues to accelerate, adapting existing enterprise systems to changing business practices and advances in information and communications technology (ICT) has become a significant problem. Not only must current systems be virtualized for execution on cloud computing systems, but software must also be restructured with higher flexibility to meet expanding business requirements, such as coordination with other services. However, it is typically not feasible to re-implement an entire system due to the high cost and risk of system malfunction. In this paper, we propose an approach to transforming a system in order to enhance its flexibility and expandability. Our approach works by extracting each part of the system individually, analyzing its characteristics, and identifying an appropriate implementation strategy based on those characteristics. Three techniques are used to support this approach. First, the structure of the system and the relationships between functions are visualized by analyzing the program files. Next, the business logic complexity, update frequency, etc. of each program is characterized. The feature values obtained are assigned to the heights of their corresponding structures on a software map and are used to characterize and prioritize functions or programs. Finally, the identified functions are analyzed using symbolic execution, and the rules and calculation methods used in the business are extracted as decision tables in a readable format. This approach enables an existing system, the system of record (SoR), to be transformed by extracting its features and identifying the best solution for each feature, such as defining it as a service, using it with a business rules management system (BRMS), or using the program as is.