We encourage chief information officers (CIOs) to play more active roles in organizational level strategy making in the digital era and examine how CIOs could lead their organizations’ digital innovation initiatives. We propose that it is the CIO’s effectiveness in issue selling (i.e., the acts that are directed toward affecting top management teams’ (TMT) attention to and understanding of strategic issues), rather than his or her structural position, that directly influences the level of organizational digital innovation success. Nevertheless, CIO structural power should not be overlooked because it could amplify (i.e., positively moderate) the impact of CIO issue selling to digital innovation outcomes. In addition, we identify four enabling forces of CIO issue selling effectiveness: (1) CIO strategic decision-making authority, (2) CIO/TMT partnership, (3) CIO information technologies (IT)–related strategic knowledge, and (4) CIO political savvy. Matched-pair survey data collected from senior business and IT executives of 179 organizations largely support the research hypotheses.