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As widely recognized in the literature, information technology (IT) investments have several special characteristics that make assessing their costs and benefits complicated. Here, we address the problem of evaluating a web content management system for both internal and external use. The investment is presently undergoing an evaluation process in a multinational company. We aim at making explicit the desired benefits and expected risks of the system investment. An evaluation hierarchy at general level is constructed. After this, a more detailed hierarchy is constructed to take into account the contextual issues. To catch the contextual issues key company representatives were interviewed. The investment alternatives are compared applying the principles of the Analytic Hierarchy Process (AHP). Due to the subjective and uncertain characteristics of the strategic IT investments a wide range of sensitivity analyses is performed.

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