This qualitative study considers how gender affected women vice presidents of student affairs' (VPSAs) or senior student affairs officers' (SSAOs) professional experiences and career trajectories to gain insight into the influence of gender on all women professional's working experiences and ability to advance in the field. Although there is a substantial body of literature focused on women in higher education, few studies focus exclusively on women professionals in student affairs and center gender in examining women's underrepresentation in student affairs' most senior leadership positions. By applying aspects of comparative case study methodology (Bartlett & Vavrus, 2017) to the individual cases of six women VPSAs or SSAOs, I learned gender is a consistent external and internal force on women professionals, which colored their daily work experiences and shaped their professional choices, behaviors, and career paths. This study contributes a needed organizational theory perspective to inquiries of women's experiences in student affairs through its theoretical framework built on Acker's (1990) five processes of gendered organizations, which illuminates the hidden ways gender is perpetuated and operationalized often to the disadvantage of women professionals at every career stage. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]