This paper analyses factors contributing to under representation of female teachers in headship positions in Eldoret Municipality Kenya. The study was guided by socialization theory to hierarchical gender prescriptions which gave three distinct theoretical traditions that help, understand sex and gender. Descriptive survey was adopted for the study and the study used both quantitative and qualitative techniques. The study employed stratified sampling, simple random and purposive sampling. A sample of 105 respondents from 10% of the target population were used where 2 Municipal Education Officials (TAC tutors), 8 head teachers, 80 teachers and 15 committee members were purposely selected for the study from 15 public primary schools randomly selected in the Municipality. Data were collected using questionnaire and interview schedule. The questionnaire was administered to teachers and committee members, whereas interview schedule was administered to head teachers and TAC (tutors). Data were analyzed using both descriptive and inferential statistics. Frequencies, percentage and Chi-square (x²) were employed in the analysis. It was established that women were not discriminated against in headship position but other obstacles, like unfair promotion procedures, gender stereotyping and rigid career path ways hinder women most. The author recommends that the educational policy should provide equal opportunity for male and female and that the conditions required in the appointments and recruitment should ensure that they eliminate discrimination. The study is significant to female teachers in headship positions as it calls for the need to improve on their roles as mentors to other young female teachers in the profession. It also contributes to the ongoing studies on the place of women in leadership and development.