The dearth of women in executive positions within the field of information technology (IT) has been studied extensively in the corporate sector. That is not the case within higher education, despite the data collected showing that women attain the top executive role--that of the Chief Information Officer (CIO)--at much better rates than their corporate counterparts. Given this discrepancy, as well as the importance of technology in today's society, research was needed into the structural factors contributing to women's executive attainment in higher education IT organizations. Using a sequential explanatory mixed methods design, this dissertation study compared women and men higher education CIOs along a variety of individual and organizational characteristics, and examined elements related to women's ability to attain the CIO role. The study combined quantitative descriptive data on higher education CIOs, gathered via a web-based questionnaire and analyzed for significant differences between women and men in the population, with women CIOs' qualitative explanations of the quantitative findings via semi-structured interviews. 188 women and men (38 women and 150 men) participated in the questionnaire, and nine women who filled it out participated in the semi-structured interviews. All participants were higher education CIOs working at EDUCAUSE member institutions. Integrated findings from this study suggest that though few demographic differences exist between women and men in the population, higher education IT culture is based upon masculine norms, and as such, perpetuates biases against women leaders in the profession. Despite cultural norms that potentially dissuade women from working in the field, a number of environmental characteristics emerged associated with women's ability to secure the CIO position. These included stimulating work that is connected to the mission of higher education; flexible work options available at different points in IT employees' careers; the presence of women executives in academic institutions; and a nationally based professional development community focused on mentoring future generations of CIOs. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]