This analysis provides an overview of the Freshman Transition Program at the Community College of Baltimore County (CCBC) and Towson University, which implemented an innovative business model and strategic partnership to successfully transition students from one institution to the other. The Freshman Transition Program provided a second chance to transfer students who successfully completed a portion of their studies at CCBC with the plan to enroll at Towson University. Over a span of 5 years, the Towson University Freshman Transition Program grew from 39 students in the initial cohort to approximately 270 students by the fifth year (McColloch, Mince, Gamble, & Duda, 2013). This study specifically addresses the context which led to the creation and success of the Freshman Transition Program at CCBC and how effective leadership contributes to successful implementation and program outcome achievement. Evidence for this study was gathered through reviewing a detailed program overview and data, an interview with the program's director, and research and analysis of current literature applying to transition programs. The partnership between CCBC and Towson University provided a notable framework for breaking down traditional silos between community colleges and four-year institutions, implementing leadership theory in program development, and strategic considerations for duplicating programs across different institutional types.