The article reveals the complex features of enterprise development, including large, medium and small business enterprises in Russian regions. It shows the close connection between the socio-economic development level of the regions, their investment attractiveness and the development of the enterprises, as well as the need to take into account the indicators of the development of enterprises in the information systems of the federal and regional levels in the conditions of the digital transformation of the economy. Both the system of indicators and the aggregated index for the analysis of the group of enterprises in the region are proposed. On the basis of cluster analysis, groups of regions are identified by the level of enterprise development, and a description of each group is given. It is shown that the regions with a low level of socio-economic development belong to the groups with the most unfavorable indicators of enterprise development. In such regions, the share of large business enterprises and innovative activity of enterprises is significantly lower, the demographic processes of enterprises are less favorable, the tax share indicators on the profits of enterprises in the total amount of taxes in the region are significantly lower, etc. The definition of the concept "strategic sustainability of the enterprises of the region" is given on the basis of the conducted researches. The group of enterprises in depressed regions cannot be called strategically sustainable. The perspective directions of use of the offered approaches to the analysis of activity of the enterprises for regulation of regional development are defined.