Although companies have to concentrate on effort to save cost to survive competition, transportation costs are taking more portions in total sales costs due to globalization in the modern times. It is the reason why Transportation Management System TMS is getting more important. However, it is practically difficult for the system to fit to all of transportation environments and actually many problems are taking place with the system. Therefore, a new idea is necessary to solve such problems fundamentally rather than temporarily or superficially. To do so, if TRIZ, which is a theory that systematically establishes creative ideas on the basis of patent analysis, is employed, it can bring forth a guideline with some creative principles that can be applicable in drawing out innovative ideas based on conceptual shift. The present study aims to propose a methodology of how TRIZ should be applied to solve the problems that happen in TMS as a whole. Particularly, the study focuses on how to design customized TMS system that can be employed for each of different situations in a creative way.