The ways in which high schools allocate their staffing and assign individual roles related to career development are pertinent to students with and without disabilities accessing career preparation that equips them for employment following graduation. Rural school districts can especially benefit from strategic role allocation that addresses gaps often relating to available staffing, formal disability resources, and local opportunities for work. This mixed methods study explores the roles of school staff and administrators within and across 10 rural Tennessee districts for supporting the career development of students with disabilities as well as how they come to assume these roles, their views on such roles, and the programmatic strengths and gaps that result from the collective services they provide. Data suggest that special educators often perform a vast majority of responsibilities in this area and may feel overwhelmed by the number of roles they must play to adequately connect students with disabilities to the knowledge, experiences, and linkages required for them to successfully obtain and sustain work. Further, results indicate that staff often self-decide their own roles in this area or assume tasks upon collaborating with others, rather than receiving explicit delegation from their supervisors. Implications for future research, practice, and policy include recommendations for extending and clarifying the roles of CTE educators, school counselors, related service providers, administrators, and others for supporting the efforts of special educators and paraprofessionals in career development. By intentionally providing training and time allotment for cross-departmental collaboration and community partnership, districts can ensure that students with disabilities are able to access a constellation of formal and informal supports and that staff can develop capacity to prepare all students with disabilities for work. [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.]