Information systems (IS) exist in order to intensify the information flow within an organization, at all levels, specifically to allow set of data to reach the designated person, in the right format, and at the right time, generating a positive and beneficial contribution to the organization. Therefore, it is essential to investigate their intended purpose and how they affect the organization’s effectiveness in particular. This paper aims to investigate two different implementations of information systems in two organizations and understand the impact these implementations have on the respective organization’s effectiveness. We use three antecedents, namely, time-saving, workload, and system reliability, to distinguish users’ perceptions and experience with the system and how they affect the organization’s effectiveness. An interpretative method is used, due to the paradigm’s focus on social constructions and human interpretations to explain reality. The result of the findings shows that the implementation of a new IS has a greater impact on an organization’s effectiveness, compared to an older system that gets updated and add-ons. By comparing diversities between different implementations of information systems, focusing on how the chosen approach affects the effectiveness in each organization, a better grasp, and understanding of an area that lacks research and attention is highlighted.