There is evidence that many businesses are investing in complex technological innovations such as enterprise information systems with the aim to improve their operations. This technological innovation however, tends to have a disproportionate focus on either the purity of the system (system effectiveness), or the operational effectiveness. The resulting lack of alignment is detrimental to the long-term enterprise benefits because of failure to achieve the real value of innovation. Although the literature has discussed system effectiveness and operational effectiveness extensively, there is not a comprehensive discussion in regards to the alignment between the system effectiveness outcomes of a technological innovation and the operational effectiveness outcomes. This study explores the linkages and interactions between the two previously defined models, examining the influence of several organisational factors such as strategies, on achieving an alignment that maximises benefit to the enterprise. This research uses a qualitative approach, based on unstructured and structured interviews with employees at different levels of two large service organisations, to build on the existing literature and to further confirm and refine a theoretical framework.