Enterprises are now seeking to cater the needs of their business change to improve business agility and to increase information technology flexibility. They have transformed with the initiative of implementing service orientation from their existing information technology infrastructure to a managed services environment. This requires a step-by-step process in the implementation of the service orientation initiative. In this paper, the four-phase process of implementing service orientation initiative derived from the related literature is taken to the case study of seven case enterprises to check for its applicability in wider enterprise settings. It has resulted that this four-phase service orientation initiative process has been clearly employed and agreed upon by most of the case enterprises. It is therefore believed that the four-phase process can be a generic initiative process of implementing service orientation for any enterprises to maintain viability in a services environment.