The problem addressed in this study was the lack of retention of women in upper-level leadership positions in higher education institutions. The purpose of this qualitative exploratory case study was to explore mentoring throughout career progression for women in upper-level leadership positions in higher education institutions and their current job satisfaction. The purpose of this study is to explore the experiences of mentorship in retention, job satisfaction, and achieving upper-level leadership positions for women in higher education. The theoretical framework for this qualitative case study included gender schema theory and job satisfaction theory. The participants were 33 women in higher education leadership positions who completed a job satisfaction survey. The primary data collected for this qualitative case study was from seven women participants who participated in a Zoom interview. The data from the interviews were transcribed, coded, categorized and used to develop themes. The survey data was also used to develop a theme. Six themes emerged from the data. Results included that when the women received mentoring in their career, they were better equipped to navigate the roles as their careers progressed, and they reported higher job satisfaction. However, there were limited opportunities for formalized mentoring outside of a supervisory relationship. Additionally, participants experienced gender stereotyping, causing job dissatisfaction. Recommendations for practice include the creation of more mentoring opportunities for women in higher education and to work on breaking down the gendered, stereotyping environment of higher education. Recommendations for future research include studies exploring the efficacy of mentorship for women in higher education and the role of mentorship in reducing gender stereotyping in higher education. [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.]