The goal of the paper is to assess the level of digital maturity of selected companies in two industries (banking and retail) in the Republic of Macedonia based on defined methodology. The results confirmed that companies in the sample fully understand the benefits of digital transformation and strive to reach higher levels of digital maturity. Although companies from both industries are progressing well and the overall level of digital maturity is set between levels 3 and 4, banks are step forward reaching level 4 i.e. customer-driven while retail companies are on transitional level.