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Healthcare and behavioral healthcare reform are sweeping across the United States to improve health outcomes, increase client satisfaction, and to decrease healthcare expenditures through statewide transitions to Medicaid managed care (MMC). Leaders of behavioral health organizations face significant challenges when implementing wide scale organizational change. A case study design was used to explore senior leaders’ experiences with transitioning from a fee for service environment to MMC at a behavioral health organization, which operates in the Northeastern region of the United States. The Baldrige excellence framework was used as a conceptual lens to assess the organization’s effectiveness in key factors. Senior leader interviews (N = 7) and analysis of the organization’s archival data were used to inform the study. Senior leaders identified preparation, communication, and marketing assisted in strategic readiness and capacity for organizational change. State delays and regulation changes in MMC implementation, decreases in reimbursement rates, and staffing issues impacted implementation of MMC. These findings were aligned between senior leader interviews and archival data. Recommendations included documentation of senior leader decisions, creation of an organizational strategic action plan for significant changes, capturing outcome data, diversifying funding sources, and implementing workforce satisfaction surveys. Senior leader insights can be used to inform the behavioral healthcare field of challenges encountered and strategies used to implement an MMC transition to improve the lives of individuals served and effect positive social change.