The present study contributes to the body of work addressing the need for diversity in the educator workforce. The study examines six grant-funded projects designed to increase the diversity of teacher candidates, support these candidates through licensure, and ultimately increase the diversity of the teacher workforce in Ohio. Data was gathered from Principal Investigators and other project members via mid-year and end-of-year interviews (N = 12) and analyzed using qualitative coding methods. The analysis surfaced common themes among program features, program implementation, and challenges programs encountered. The findings suggest that effective programs to diversify the educator workforce could benefit from program development that makes intentional use of several key strategies: (1) collaborative processes and relationships; (2) programmatic and individual student support; (3) targeted, personal approaches to recruitment; (4) intentional planning for financial sustainability (including the use of more than one funding stream); and (5) the creation of specific pathways from high school to career. This study further identified both internal and external systemic challenges programs encountered and highlighted effective methods for resolving issues where possible, while also identifying challenges that remained intractable.