This paper focuses on the experiences of six Chilean female headteachers. It addresses their career progress, and the facilitators and barriers, as well as the challenges they encountered in accessing and enacting school leadership. The six participants were drawn from all three of Chile's school types -- public, semi-private and private -- in what is a differentiated system. The findings demonstrate both differences and similarities in participants' experiences, across all three school sectors. A major difference relates to the additional barriers faced by public sector school leaders, compared with participants in the private and semi-private schools.