Since its first introduction, ordinary fuzzy sets have been extended to new types of fuzzy sets as a tool of artificial intelligence techniques. One of the recently introduced fuzzy sets, “Circular Intuitionistic Fuzzy (CIF)” sets enable us to take into account instability of the membership and non-membership degrees with a circular area & its radius. In this study, we first introduce Interval Valued CIF (IVCIF) sets and their arithmetic operations to better incorporate the uncertainty and cover a broader domain. Then, we introduce a novel IVCIF Analytic Hierarchy Process (AHP) method and apply it to evaluate Digital Transformation (DT) projects with complex nature. DT projects requiring fundamental changes in processes, business models and cultures of the companies, contribute a significant value to the companies and increase their market shares; so that they can achieve long term success and competitive advantage. On the other hand, DT problems which are usually ill-defined and include incomplete information based on human judgments, necessitate fuzzy representation. For the success of a digital transformation and to contribute excellence in engineering applications, DT projects should be carefully analyzed. For these reasons, we focus on DT project evaluation problem in application. Also, sensitivity & comparative analyses are performed.