Residency programs across the United States are searching for ways to improve surgical skills and operative experiences in obstetrics and gynecology residencies. We developed an obstetrics and gynecology residency program that offers a flexible curriculum, referred to as tracking, to address these needs. Curriculum content was developed using a modified Delphi method, using input from experts in medical education and obstetrics and gynecology. Outcome data were collected on trainees who graduated between 2016 and 2019, including postgraduate fellowship placement and our residents' achievement of surgical minimum requirements based on procedure logs. Trainees from this program have consistently exceeded minimal surgical requirements in all areas, regardless of tracking preference. Since the beginning of the program in 2012, more than 60% of graduates have matriculated into fellowships. Flexible curricula, such as tracking, offer one approach to a changing climate of medicine. The ability to offer flexible, focused, and individualized training is an approach with great potential to produce graduates who excel in all areas of obstetrics and gynecology while sharpening skills specific to their areas of interest.