Proposed study aims to investigate the digital transformation of Greek small and medium enterprises (SMEs), with a particular focus on their digital maturity and the strategic and organizational factors contributing to digital transformation. The research issue of digital transformation is attracting considerable interest among academics and business practicians since COVID-19 accelerated the procedure of implementing Industry’s 4.0 principles all over global economies. Quantitative research on 147 Greek SMEs revealed most important issues on how these businesses implement digital transformation, factors accelerating or decelerating the process, barriers and expected outcomes. Research enlights how SMEs face the transition to digital business and reveals the factors that can facilitate the whole process. Results can be valuable for stakeholders enabled to digital transformation process from both business and academic point of view, while there exist aspects that can contribute to policy makers / motivation developers in state’s level as well.