The development of the digital economy can aggravate the existing problems of the Russian labour market (the high level of informal employment, low labour mobility, growth of precarious employment etc.), can cause a growth of technological unemployment. Automation and digitalization would change most task sets within particular occupations, would radically change distribution of workers by occupations. By 2022, about 53% of labour forces can be re-trained. The Russian employment services have to become an effective structure of mass retraining. The analysis of in-depth expert’s interviews reveals an organizations problem of retraining programs (the focus on the functional tasks of the employment services, the low efficiency of programs, the insufficient financing, the lack relations of the employment services with employers, etc). The authors focused on a problem of interaction between the federal level (Federal service of labor and employment) and regional departments and the employment services. Now, it is necessary to strengthen the role of the federal bodies for the formation of a proactive employment policy. This measure will help us to move from the existing fragmentation in employment management, to transfer the experience and knowledge of the Federal service to all regional structures. Active work of employment services will help to reduce social inequality, will not allow excluding a most of Russian workers from high-paid, high-tech branches of the digital economy.