The main objective of this paper is to investigate the SMEs‟ leader perspective about the basic factors influencing the transformation into digitalization by SMEs they lead, using technological, organizational, and environmental (TOE) Model. The data were collected from 61 SMEs leaders in Oman, to achieve the study objective TOE model has been adopted. Internal consistency and data normality, and factor analysis were implemented. Structural equation modeling (SEM) used to test the proposed hypotheses. The outcomes of SEM indicate that TOE factors are significantly affects the ability of SMEs to digitalize their business process. The study findings come in the context of Omani definition of SMEs. More, no control was made for industry type to which SMEs participants are belong. Leaders of SMEs should frame strategies to simplify the digital transformation of their enterprises and attempt to provide organizational and technological facilities that will smooth their digitalization which will improve SMEs capabilities, as well as, increasing the international competitiveness of the SMEs. To the best of the authors' knowledge, this study is one of the first that investigated the digital transformation among SMEs from the leaders‟ perspective in Oman.