Introduction. In the healthcare system, as in any other field, the presence of managerial personnel with a set of professional competencies is currently an essential condition for ensuring full functioning and development. The position of chief physician requires knowledge and skills both in the field of medicine and in the sphere of management. Within the framework of the "Portrait of a Chief Physician" study, information about the education, work experience, and main career paths of heads of medical organizations was examined and analyzed from the perspective of training and retraining managerial personnel for the healthcare system, their development, on-site adaptation, and performance improvement. The aim of the study was to examine and analyze the level of education, qualifications, length of service, practical work experience of heads of medical organizations, as well as their career progression. Materials and methods. The study employed a survey method using a questionnaire consisting of 63 questions grouped into four blocks. A total of 2,462 chief physicians participated, of whom 1,135 were women and 1,327 were men. Results. It was found that 99.5% of respondents had a medical degree as their first education, while others had degrees in economics, management, or other fields; 37.8% had a second degree; 4% of respondents held a Doctor of Sciences degree; and over the past five years, 91.8% of respondents had completed training in the discipline "Healthcare Organization and Public Health," with 87.2% of respondents agreeing with the statement about the need for training. Half of the respondents' total work experience was in positions as healthcare system organizers, and the difference between the average medical and managerial tenure was about 12 years. The overwhelming majority were appointed to the position directly, while only one-sixth came from a managerial talent pool. Conclusion. The information obtained in this study is important from the perspective of training healthcare system personnel and can be used for planning programs of additional professional education in the specialty "Public Health and Healthcare," as well as other continuing education programs in the fields of jurisprudence, health economics, management, project management, etc., aimed at improving the performance of chief physicians.