The ways in which high schools in rural U.S. communities allocate their staffing and assign roles related to career development impact the preparation of students with disabilities for future employment pursuits. This mixed methods study explored (a) the roles of 291 school staff and administrators in supporting the career development of students with disabilities, (b) how they came to assume these roles, and (c) how they viewed their roles. Findings indicated that special educators self-decided an overwhelming majority of roles in this area and could benefit from increased contributions from school staff in other positions to support the work preparation of students with disabilities. We offer recommendations for extending and clarifying the roles of staff in these rural districts.