Enterprise resource planning (ERP) system has been one of the most popular business management systems, providing benefits of real-time capabilities and seamless communication for business in large organizations. However, not all ERP implementations have been successful. Since ERP implementation affects entire organizations such as process, people, and culture, there are a number of challenges that companies may encounter in implementing ERP systems. Recently, some universities have begun replacing their legacy systems with ERP systems to improve management and administration. This thesis focuses on challenges of ERP implementation between corporate and university environment. I review previous studies that determine Critical Successful Factors (CSFs) and risk factors to implement ERP in both environments. Particularly, case studies in this thesis emphasize the organizational dynamics involved in ERP implementation by using CSFs and three phases of framework by Miles and Huberman (1994): antecedent condition, implementation process, and outcomes. This study uses findings from the case studies to assess ERP readiness and CSFs' fulfillment. The results from this study contribute to contextual understanding of distinctive challenges in ERP implementation between corporate and university environment.