The purpose of the study was to determine the state of the market for information systems and services in health care, and to develop requirements to software suitable for 85 territorial compulsory healthcare insurance (CHI) funds as an important component of national e-health in Russian Federation. The authors have found out that reliable solutions for the digitalization of CHI are not yet available and revealed the reasons and disadvantages of the current situation in the healthcare-related IT market, and the means to improve it. To develop proposals for the creation of a unified software package for data processing and digitalization of business processes at territorial CHI funds, the authors fulfilled reengineering of CHI business processes. Particularly, they analyzed the information system currently operating in the fund of the Leningrad Region and estimated the time required for manual operations that can be sufficiently reduced. As a result, specific measures for the digitalization of the activities of the territorial CHI fund were worked out, along with the timing of these measures to be fulfilled, financing, and evaluated investment attractiveness.