As part of efforts to become more interdisciplinary, socially embedded, and innovative, leaders of a large college of education reimagined a program originally designed to retain struggling students to target students interested in nontraditional educational careers (e.g., nonprofits). Researchers in this study explore reasons why this program has increasingly become a program of choice through both quantitative and qualitative analyses of institutional data across the program's history and surveys of current students and instructors. Findings about shifting demographics of students enrolled in the program toward nontraditional students who appreciate the accessibility and flexibility of the online modality, as well as shifts in program focus on preparation for a broader range of educational career options are presented. Findings also highlight the possibilities of this type of program to prepare students for further educational opportunities, including graduate programs, to also facilitate university-business partnerships. Implications for continued improvement and growth of this program and the design of similar programs targeting the preparation of students for non-traditional teaching positions are also discussed.