In this study, the effects of IS strategic leadership on organizational outcomes are examined from the perspective of CIO strategic roles. A field survey is conducted that collects data from 110 matched pairs of CIOs and business executives within organizations. Our findings suggest that strategic leadership significantly affects both organizational benefits and information system quality. Further, we found that IS quality significantly mediates the relationship between IS strategic leadership and organizational benefits. We also note that IS vision significantly moderates the relationship between IS strategic leadership and IS quality, although it does not moderate the relationship between IS strategic leadership and organizational benefits or the relationship between IS quality and organizational benefits.