Hiring and sustaining qualified executive leaders at schools and programs for the Deaf continue to be challenging for board members and communities. More information is needed to understand issues contributing to the retention and recruitment of these executive leaders. The purpose of this qualitative case study was to understand factors that contribute to retention and recruitment in these positions and to learn possible solutions for overcoming challenges. An economic labor market theory for superintendents informed the study. Data were collected via interviews with 11 executive leaders from public and private schools for the Deaf from different regions of the United States; the schools varied in size and enrolled students from preschool through 12th grade. Interviews were video recorded and transcribed into written English for coding and thematic analysis. Participants identified concerns including inadequate preparation for the role specifics, challenges of the scope of responsibilities and stressors of the position, the need to defend the worth of these schools, skills needed for working with a governing board, inadequate compensation, and the locations of the schools. Participants expressed a need for more support, continuing education, mentoring, and enhanced compensation. Key recommendations included increasing preparation programs for and enhancing ongoing leadership training in Deaf education, enhancing the capacity of the schools for succession planning, providing mentoring for individuals within existing programs to become executive leaders, and focusing on the positive elements of the schools and their locations when recruiting executive leaders. Improving and stabilizing the leadership capacity within the schools elevates the quality of education provided to Deaf and hard-of-hearing students and leads to positive social change. [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.]