Researchers have used previous literature to suggest that Black women face challenges and obstacles in seeking leadership roles at higher education institutions (HEIs). Many of these Black women have consistently and pervasively faced prevailing stereotypes, biases, and barriers as they seek career advancements at online HEIs (Nigar, 2020; Tarbutton, 2019). This qualitative phenomenological study was undertaken to examine the intersectionality of gender, race, and personality traits of Black women leaders who hold positions of department chair level or higher in HEIs. Using the theoretical framework of Black feminist thought, this research was conducted to understand better the lived experiences of a selected group of Black women in leadership roles at HEIs. Purposive sampling of ten Black women leaders from Texas-based HEIs allowed for the participants to engage in virtual open-ended question interviews via video conferencing, Zoom. The participants shared experiences on their career trajectory and barriers encountered on their journey and reflected on what helped them overcome obstacles while seeking leadership roles at HEIs. The procedures of initial coding, NVivo coding, and descriptive coding were utilized to transcribe the obtained data and create three main themes and 11 subthemes. The three major themes identified included support systems, personality perceptions, and career pathways. The results of this study provide fresh viewpoints on the difficulties faced by Black women seeking leadership roles at online HEIs. The participants' viewpoints may also help improve academic environments to identify potential leadership approaches for developing Black women to acquire leadership roles.