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How should the effectiveness of Chief Information Officers (CIOs) in organizations be assessed? What are the primary antecedents of their role effectiveness, particularly as assessed by their top management teams (TMTs)? Despite a wealth of normative and prescriptive writings about what roles CIOs should play in contemporary firms, there has been limited empirical research on the above two questions. This study addresses the above questions, particularly with respect to the effectiveness of the CIOs in the healthcare sector. Based on survey data from CIOs and members of the TMTs, we find that there are six salient CIO roles: business strategist, integrator, relationship architect, utility provider, information steward, and educator. Further, CIO capabilities, in the form of business and strategic information technology knowledge, political savvy, and interpersonal communication makes CIOs effective, particularly in the roles of business strategist, integrator, and relationship architect. High levels of engagements between the CIOs and TMTs do not directly impact CIO's role effectiveness, but are mediated by the effects of CIO capabilities. These findings have significant implications for researchers and senior information systems (IS) executives.