Career development awards are a successful strategy to facilitate the advancement of physician-scientists trained in obstetrics and gynecology (OBGYN) toward a path of investigative independence. While these funding mechanisms can be effective approaches to developing the career of future OBGYN scientists, optimizing the probability of obtaining these awards requires determining the appropriate career development award for the applicant. There are many details and opportunities that need to be considered when deciding on the appropriate award. Some of the most sought-after awards are those that integrate career development and applied research, such as the K-series awards supported by the National Institutes of Health (NIH). A quintessential example of an NIH-funded mentor-based career development award to support the scientific training of an OBGYN physician-scientist is the Reproductive Scientist Development Program (RSDP). In this study, we provide data on the academic achievements of past and present RSDP scholars and discuss the structure, impact, and future of the RSDP, a federally funded K12 program dedicated to women’s health for OBGYN scientific investigators. As healthcare is changing and physician-scientists comprise a unique and valuable part of the biomedical workforce, programs such as the RSDP are critical to maintaining a well-trained pipeline of OBGYN scientists to maintain and challenge the leading edge of medicine, science, and biology. Supplementary Information The online version contains supplementary material available at 10.1007/s43032-023-01234-8.