Digital transformation has been an important issue for all kinds of companies, especially after COVID-19, since risks increased and the procedure of transforming traditional forms of doing business was accelerated. This chapter evaluates the digital transformation of Greek small and medium enterprises (SMEs). A series of different aspects are evaluated by using a quantitative approach, including operational elements such as digital maturity, digital transformation strategy, and implementation of specific technologies driving this process. Results indicate a positive relationship between digital maturity and digital transformation strategy, alongside employees' training and investments in new technologies. COVID-19 delayed Greek SMEs transformation procedure, with main technologies related with sales and collecting customers' data. The research contributes to the evaluation of the digital transformation progress in Greek SMEs by providing insight on most significant technologies used and the overall strategic planning implemented.