The paper discusses a pilot study aimed to identify the factors of development of the regional market for corporate voluntary health insurance in St. Petersburg during the period from 2015 to 2018. Based on the review of scientific works of Russian and foreign authors as well as the analysis of international experience, the key factors influencing the functioning of the corporate voluntary health insurance market are identified including the economic development of the region, demographic situation, changes in the labor market, accessibility of medical care, and personal characteristics of the insured. The results of quantitative modeling showed that the development of the corporate voluntary health insurance market in St. Petersburg is influenced by the factors related to the economic well-being of the region and the state of labor market. Such factors as the average per capita income of the population, the unemployment rate as well as the index of prices and tariffs for paid medical services turned out to be significant. In addition, a qualitative analysis of the demand for corporate voluntary health insurance was carried out. The analysis of a structured survey Russian and international companies managers proved the following assumptions: voluntary health insurance policies are more often offered to employees of large and medium-sized organizations operating mainly in Moscow and the Moscow region compared to companies whose main number of employees work in St. Petersburg and the Leningrad Region; international companies are more likely to provide voluntary health insurance policies to their employees than Russian ones. The study offers practical recommendations to stakeholders — the authorities, insurers and employers.