This study examines the application and acquisition process of individuals completing a principal licensure program to obtain school administrative positions over a period of five years. While relatively low compensation and high-pressure accountability demands were viewed as deterrents by those deciding not to seek principalships, the majority of the study participants actively sought and obtained school administrative positions. Gender differences were examined in the areas of applying for positions, interviewing, and number of job offers. Reasons for not applying for principal and assistant principal positions were also examined.