Mental health challenges among students remain a complex and widespread problem facing school leaders. Though schools are a front-line pathway for providing mental health services, many struggling youth are not receiving the professional help they need (Atkins, Hoagwood, Kutash, & Seidman, 2010; Findlay, 2017). Creative and collaborative solutions are needed to bridge the mental health gap. School leader support is essential to the successful implementation of mental health interventions (Forman, Olin, Hoagwood, Crowe, & Saka, 2009). This paper summarizes the novel approach taken by school and community leaders in one rural Ontario community who jointly piloted a school-based social worker (SBSW) role to support secondary schools in two districts. Interviews with five district leaders (four involved in designing the intervention and the SBSW who piloted the role) reveal conditions necessary for the pilot to take place, as well as leader involvement in setting up, supporting, monitoring the new role. Interviews highlighted multiple ways which the pilot improved student mental well-ness: one-on-one and group counselling sessions, charting fresh pathways networks of support available to students, creating a safe space for student and staff drop-ins, among other benefits to schools and stakeholders involved in the pilot. Results also detail three challenges leaders encountered along the way: stakeholder agreement, role clarity, and the temporary design of the role. Findings underscore how school-based social workers show promise in addressing rising mental health challenges.