In the last years, as object-oriented software systems became more and more complex, the need of having tools that help us to understand and to assess the quality of their design has increased significantly. This applies also to enterprise applications, a novel category of software systems. Unfortunately, the existing techniques for design?s understanding and quality assessment of object-oriented systems are not sufficient and sometimes not suitable when applied on enterprise applications. In the current Ph.D. we propose a new approach which increases the level of understanding and the accuracy assessment of the design of enterprise software systems.