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Based on the upper echelon theory, this paper studies the relationship between the individual characteristics of the Chief Information Officer (CIO) and organizational innovative usage of information technology (IT) by examining both the CIO's demographic characteristics and personality traits. Survey results from 89 CIOs strongly support our proposition. A CIO's personality traits of openness and extraversion and CIO's demographic characteristics of educational level have strong impact on the organizational innovative usage of IT even after controlling for organizational variables such as the organization's business strategy, outsourcing of IT operations, IT department age, and IT budget relative to revenue. This paper contributes to the age-old debate on whether managers matter in deciding an organization's strategy.