Despite huge global spend on IS/IT, empirical evidence shows many of these investments do not deliver expected benefits. Benefits are realized when organizations attend to contextual factors surrounding the implementation of IT and not just its technical implementation. Culture, as a contextual factor, has been shown to have a strong influence on the way IS/IT is adopted, used and exploited. We draw from IS organizational culture studies to show how individual/group IT cultures (IT culture archetypes) offer a user-centric perspective on benefits exploitation from IS/IT investments. The majority of benefits are achieved later into the lifecycle of an IS/IT investment, after implementing the IS/IT resource. Thus, this study investigates post adoption experience of an organization’s IS/IT investment, an important systems lifecycle stage that has received less attention in the IS literature. We adopt a single in-depth case study approach incorporating a three stage mixed data collection strategy. From a theoretical perspective, IT culture offers an intuitive approach to address IS/IT benefits management challenges during the post-adoption stage. From a practitioner perspective, we believe findings from this study, will offer several managerial implications for business and IT managers on specific actions to realize greater benefits from their IS/IT investments.