The current literature on school counselor job satisfaction does not address the experiences of school counseling directors. This is a unique set of counselors due to their role as leaders and supervisors in the building. Therefore, this study sought to better understand the experiences of school counseling directors in relation to job satisfaction and leadership. The researcher collected data through 10 interviews with participants having met the criteria of serving as a school counseling director of a middle or high school, supervising a department of at least two counselors, and working in the role for at least two years. Data analysis showcased the different expectations in the role of the school counseling director in addition to four major themes: Intentionality, Leadership Training and Knowledge, Overload of Responsibilities Assigned to Role, and Sacrifice. The subthemes for Leadership Training and Knowledge include limited counselor-specific preparation, limited recognition of leadership style, collaboration, and influence of administrators. The subthemes of Sacrifice include time to complete duties and gender-related influence on role acquisition. These themes are discussed in relation to current research as well as in regards to implications about the expectations of the school counseling director’s role, gender influence, leadership training standards and programs, and wellness. Recommendations for further research about school counseling directors, district-level supervisors, and leadership training are also given.