Education remains one of the most gender imbalanced fields, with disproportionately fewer women in higher levels of leadership. Women who reach leadership positions in education experience many triumphs and tribulations during their tenures as principals, assistant superintendents, and superintendents. The experiences of these women in their various administrative levels of leadership can provide important insight into the reasons for their success as women superintendents in Texas. This research has probed the career trajectory of nine women who have successfully attained and retained superintendencies in Texas to determine what career decisions have helped them and the challenges these women have faced in their positions. A qualitative research method, open-ended interviews, yielded several findings of what women considered important in proceeding from teaching through the various levels and ending in becoming superintendents. According to nine successful women superintendents in Texas, there are specific characteristics one can bring to the table that would really make a difference: Communication, collaboration, compassion, preparedness, hard work, and passion. All nine participants overcame challenges when climbing to the higher levels of leadership in education. These women have achieved success in the superintendency, and several factors appear to have played into the success of these women who have achieved in education’s top position.