Three women higher education Chief Information Officers (CIOs) provided their lived experiences and perspectives on barriers they encountered and methods used to overcome the barriers as they pursued and achieved their current positions. The conceptual framework intersects gendered organizational theory, feminist standpoint theory, and occupational jurisdiction. This research, being unique in specifically studying women CIOs in higher education, expands the knowledge base regarding women seeking or maintaining leadership positions by revealing many barriers encountered and that higher education information technology organizations contain gendered organizational elements. Actions organizations and individuals can take to foster gender friendly cultures are suggested.