Transition from school education to working life is a crucial phase in lives of youth. There is ample evidence that initial difficulties in this process might have lasting consequences. Main purpose of the paper is to analyze school-to-work transition of Russian youth. It is based on the results of a special survey of young people aged 15–29 conducted in 2012 in 11 regions of the Russian Federation. Funding for the surveys came from the Work-Youth partnership between the ILO Youth Employment Program and The MasterCard Foundation. Level of education is a key factor for a successful transition to the labor market. Post-secondary vocational and tertiary education, first of all the higher education, increases success of the school-to-work transition, increasing employment rate of graduates, significantly reducing risks of unemployment and economic inactivity, reducing length of transition. Young person with a university degree transited, on average, three times faster than the youth with lower secondary education. Our results indicate that young people with lower secondary education have highest risks of long unemployment and exclusion from the labor market. Combining study and work is also significant factor. Results show that young person who don’t work during their studying spent, on average, twice longer time to complete their labor market transition than students who combine study and work. Youth living in urban areas have advantage in terms of completing the labor market transition but gap between gender and settlement groups decreases with education level growth. Duration of transition to the first job highlights a dichotomous situation: a large group of youth is able to obtain a job within three months after leaving school, while smaller part of youth faces very long transition time.