Complexity of digital transformation paradigm face companies with serious challenges. This research study is settled in order to give an insight into the concept of digital transformation projects and processes, to identify initiatives, success factors, and barriers of digital transformation, as well as, to give an overview of key technologies underpinning digital transformation. As a case study a complex analysis of digital transformation industry projects is conducted. Taking into account the multidisciplinary nature of digital transformation projects and processes, a wide variety of industries in North Macedonia are included.