In a restructuring economy on-the-job training plays important role not only in raising the general level of human capital but in retooling workers for the new sectors of economy. The amount of on-the-job training in Russia has however been unsatisfactorily low compared to other countries. Main objective of this paper is to study the incentives of firms and workers to invest into employee training in Russia. Utilizing the data from Russian Longitudinal Monitoring survey for years 1999–2003, we investigate the determinants of training financing with the particular emphasis on the role of labor market characteristics. We exploit heterogeneity in the structure of regional labor markets in Russia to investigate its effect on training outcomes. In line with existing theory, it is shown that imperfections of the labor market, such as higher regional labor market concentration, lower share of small businesses and higher unemployment create incentives for the firms to provide training to employees. Hence, increase in the efficiency of the labor market is likely to bring about further decrease in the amount of employee training in a private sector.