Liberty Community Connections (LCC), a disability services provider, has a goal to be the premier support coordination agency in Pennsylvania. This goal requires that LCC recruit and retain a talented, resilient, and engaged workforce. LCC has developed a robust training institute with four arms: recruitment, social work education, training, and engagement and development. LCC wishes to use positive psychology to seamlessly align these arms and to improve staff retention and resilience. Drawing from research in positive psychology, our cohort designed a process that will serve as a roadmap for building effective interventions to achieve LCC’s goals and to leverage their core values. To facilitate the execution of the roadmap, the supplemental toolkit offers steps from the appreciative inquiry process to explore positive psychology topics and positive interventions. Once a topic or goal is identified, a comprehensive checklist supports a review of the topic’s alignment with other LCC activities and the design of an implementation strategy. Other organizations can use the findings of this paper, the roadmap and the supplemental toolkit to improve the well-being and quality of life of their staff, consumers, and stakeholders.