School staff are exposed to high levels of occupational stressors and often work within significant resource constraints, putting them at risk for burnout and secondary traumatic stress (STS). Initially developed to support community-based social workers, the Stress-Less Initiative (SLI) is a 12-session, team-based, and internally facilitated intervention intended to build personal, team, and organizational resilience to mitigate STS and burnout. Our pilot of SLI among school staff providing after-school programming in two under-resourced K-8 public schools explored its feasibility and impact in the school setting. To evaluate this pilot, we interviewed five school staff with varying levels of participation in SLI to understand their experiences, perceived outcomes, and opportunities to optimize and sustain SLI and other supportive well-being initiatives for school staff. Interviewees described SLI as timely, relevant, and personally meaningful and pointed to several associated individual, team, and interpersonal outcomes. They also highlighted opportunities for optimizing school-based well-being initiatives to support their sustainability and impact and staff engagement as well as more general staff needs and preferences for professional development. These results further our understanding of how workplace-based strategies can be implemented in school settings to support staff facing myriad stressors that impact their health, well-being, and effectiveness.