The emergence of disruptive digital technologies in the last decade has ushered in the era of digital transformation. Although digital technologies offer numerous opportunities, many enterprises still lag behind when it comes to building the necessary digital capabilities for successful digital transformation. To enable wider adoption of digital technologies and accelerate the digital transformation of enterprises, several measures are required. In order to create the necessary supporting ecosystems at both European and national level, it is important to gain a deeper understanding of the challenges faced by enterprises. For this purpose, we created the questionnaire in cooperation with the University of Maribor, the Chamber of Commerce and Digital Innovation Hub Slovenia. The questionnaire was completed by 125 enterprises in Slovenia. In this paper, we present research results that illustrate the status of digital transformation among enterprises in Slovenia and provide guidance for developing appropriate measures to accelerate the digital transformation of enterprises.