Purpose: This article aims to assess strategy and technology as key drivers of Greek businesses’cdigital transformation and compare the results to those of international studies and sources.

Methodology: A research was conducted on 124 Greek businesses from different sectors and industries with the use of an anonymous questionnaire from December 2019 to January 2020. Greek businesses were categorized as early, developing, and maturing according to their perceptions about the level of their digital maturity, and differences were identified. The results were finally compared to an international relevant survey.

Findings: Several differences were located among the Greek businesses of the three digital maturity categories as formulated after their self-evaluation, and evolution has been identified on their perceptions about their digital strategy, its existence, objectives, and structure, which can be seen developing and expanding from the lowest to the highest levels of digital maturity.

Originality: The findings can be useful in creating an initial picture of the perceptions and practices applied by Greek businesses to their use of digital technologies. They can also become a measure of comparison for the self-evaluation of Greek businesses in their efforts to digitally transform.