This study aimed to identify which digital transformation areas are prioritized in regions with different levels of innovative development. Based on the analysis of statistical information presented in reports on the control indicators of regional economy transformation, the most innovative regions were distinguished. The study scrutinized the correlation of regional economic development with the presence/absence of high-tech industries in the area, as well as compared digital skills of residents of innovation clusters with residents of other regions using data structuring and the method of analytical studies. To achieve the ultimate study goal, a number of freelancers’ profiles available on freelance marketplaces was analyzed in terms of the following categories of digital skills: programming (regardless of the programming language), translation, copywriting, SEO and SMM, design, engineering services. The sample included only the profiles of individuals registered no later than 2018 who successfully completed at least three projects. An in-depth consideration of all these data allowed developing recommendations on digitalization of the regional economy, taking into account the number of inhabitants in the region and their density. As a tool for the transformation, this study proposed the four-stage Smart Region model. In sum, the carried-out investigation revealed that the benefits of digitalization are more visible in innovative regions. Correspondingly, the regions with innovative industries are characterized by higher digital skills in the field of engineering. The obtained findings can be used as a basis for management decisions by politicians and IT industry workers striving to promote the implementation of modern technologies.