Women’s participation in collegiate sport has increased dramatically since the passage of Title IX, but there has not been a corresponding increase in the percentage of women in administrative positions. Women have, however, been successful obtaining leadership positions in conference offices, as more than 30% of National Collegiate Athletic Association Division I conference commissioners were women in 2016. This research used career construction theory as a framework to explore the experiences of these women. Findings revealed that participants constantly negotiate time spent on personal and professional obligations, and relationships created in the workplace turned into organic mentorship relationships. Participants felt that there were limited amounts of sexism in the workplace, but all discussed experiencing instances of sexism, indicating a culture of gender normalcy. Women may experience increased success in leadership positions at conference offices, compared with on-campus athletic departments, due to limited direct interaction with football and donors.