The purpose of this qualitative research, guided by Black Feminist Thought, was to examine the experiences of African American women senior student affairs officers to understand the strategies they utilized to advance their careers. Participants included six vice presidents/chancellors for student affairs (reporting directly to the president of the institution) and one dean of students reporting to the vice president for student affairs. The participants’ recounted raced and gendered experiences during their journey to becoming a senior student affairs officer into their journey of being a senior student affairs officer. Their shared experiences were based on tokenism, hyperawareness of systemic racism and sexism, and perceptions of leadership styles verses angry Black woman. They also reported support systems such as mentors, sponsors, spirituality, and family that influence their thoughts, decisions, and motivation to continue in the field of student affairs and ultimately in higher education. The implications of the study encourages and challenges African American women and other women of color who are administrators to share their professional experiences to continue to enlighten scholarship and practice while encouraging institutions to provide funding, personnel resources, and training for all employees.