The article presents the results of the research on Russian companies’ readiness for digital transformation in 2017–2021. The purpose of the study is to observe how the understanding and the attitude of the representatives of Russian business towards the digital transformation and the self-assessment of company’s readiness for this transformation has changed. The source data are the results of surveys conducted in 2018 and 2021 among representatives of companies in St. Petersburg and the Leningrad region. The paper focuses on establishing in Russian companies the Corporate Culture essential to the success of digital transformation projects. It is shown that large companies have shifted towards greater employee engagement and management support for initiatives. However, in small companies, there is still a lack of employee belief in digital transformation and a top-down implementation of digital transformation.