Purpose: This study was to present the process of web-based educational program (WEP) development and to identify factors affecting satisfaction with WEP for the certificate of healthcare managers working at the National Health Insurance Corporation (NHIC). Methods: Subjects were healthcare managers and voluntary participants of WEP. A total of 1,449 respondents were surveyed through an online questionnaire about their satisfaction with the educational contents and system. Results: The mean contents satisfaction was 3.75 (SO 0.54), and system satisfaction 4.68 (SD 0.54). According to statistical analysis, the type of certification, experience and professional career of health care management affected contents satisfaction. And factors affecting system satisfaction were the type of certification and gender. Conclusion: WEP was utilized as a pre-requisite course for the certificate program of healthcare managers. However, the development of advanced WEP is suggested to meet the educational needs of healthcare managers who have certificate or license and their job related to healthcare management.