This research investigates the current situation of higher education organizations in relation to their digital transformation process. The study goal focuses on comparison of undertaken measures and the challenges faced by higher education institutions concerned with the digital transformation of their processes. The particular emphasis is placed on the level of use and utilization of digital technologies during the teaching process as well as administrative activities that enable advanced communication between institutions, students, academic and administrative staff, and other internal and external networking processes. One of the challenges emerged evident within the HEI is the increased information digitization, i.e., transforming the current practice of working processes, respectively the conversion of physical documents to digital ones. The research results show significant difference of particular interest in the use of digital technologies in the HEI. From a comparison of the situation of Kosovo HEI, with a research conducted related to developed countries, the evidence is found concerned with the qualitative and quantitative change in the level of digital technologies use in the academic process. The main enabling technologies of digital transformation such as Artificial Intelligence, Cloud technologies, Internet of Things, are compared and ranked based on the findings from the best practices derived from the literature. The same ranking is conducted in the Kosova HEI. The synthesis of two comparisons provides with the final results of this research.