Women working in higher education information technology (IT) organizations and those seeking leadership positions in these organizations face a double challenge in overcoming the traditionally male-dominated environments of higher education and IT. Three women higher education chief information officers (CIOs) provided their perspectives, interpretations, and lived experiences regarding the gendered organization of higher education IT. This research, being unique in specifically studying women CIOs in higher education, expands the knowledge base regarding advantage and disadvantage within such organizations based on masculine/feminine and male/female working culture and experience.