Complexity of the digital transformation (Digital Transformation) paradigm and its relation to the fourth technological revolution face companies with serious challenges when it comes to keeping up with the competition or becoming a leader in operating industries. The goal of our research is to systematize, analyse and evaluate technological and business concepts of Digital Transformation, in order to identify and investigate Digital Transformation initiatives in Croatia. To accomplish this goal, we used a multiple-case study approach to gather data from experts who participated in successful Digital Transformation initiatives. Questionnaires were developed and used to gather both, qualitative background and technology-business related data relevant for Digital Transformation initiatives’ success, discussed in the last part of the paper. The limitation of this study is a relatively small number of case studies (6), as well as its local coverage, resulting therefore with conclusions, which will serve as a base for future studies. There are several background, business, and technology-related concepts or factors relevant to Digital Transformation initiatives: profile and involvement of external Digital Transformation experts; the transformation drivers and expectations. In achieving most significant business concepts for business transformation, no single one right combination of technological concepts could be explicitly determined.