The joint contributions of general education and special education staff should collectively support career development for students with disabilities in rural communities. This mixed-methods study explored the views of staff and administrators across 10 rural districts on staffing for supporting students with disabilities in preparing for work, how districts addressed career development, and how various factors affected service delivery. Findings indicated that the extent to which students with disabilities participated in career development opportunities varied based on disability types, the ways in which staff were allocated for providing services, and the extent to which partnerships were leveraged for this purpose. We offer recommendations for addressing staff needs and facilitating inclusion for students with disabilities in preparing for employment.