Up to now, the extant research has emphasized the employment of KM to gain competitive advantage for organization, but few studies address the relevance of KM environment to support the strategic objective. Gartner has proposed a classification scheme for KM implementation, which indicates that life cycle of KM practice, but the study still falls short of guiding organizations to implement the suggested KM category. The motivation and purpose of this study are induced. This study attempts to investigate the impact on KM implementation based on the organizational learning perspective. The investigation is conducted through a case study approach, where some companies with best KM practice are included. The findings based on case study results indicate that environment uncertainty, organizational orientation, and task type can influence organizational learning behavior and subsequent the deployment of KM systems. In summary, organizations may implement different KM systems depending on the environment confronted by the organization. This study is focused upon the difference in KM systems deployed by various organizations. Past research has assumed that all organizations have similar needs in KM and therefore proposed an uniform IT framework to suit organizational needs. This argument has been refuted by this research. We suggested that KM is a multi-facet phenomenon, in which many enablers contribute to the working of KM. An organization ought to establish its KM environment based on its organization imperatives and learning needs.