Previous research demonstrates that subtle changes to recruitment materials can impact an applicants’ perceived fit with the role being advertised and their inclination to apply. This has included an analysis of the effects on female applicants. Little research has explored recruitment materials for specific roles, such as headteachers. This study systematically evaluated applicant packs (164 documents; 1504 pages) for 59 Secondary Headteacher roles and found evidence to suggest recruitment materials constitute an institutional mechanism that could contribute to sustaining gender inequality in UK Headship. This analysis identifies features more likely to deter or disadvantage female applicants than their male counterparts. However, 10–22% of definitive documents (e.g. job adverts) use wording that could deter women. The salary ambiguity that surfaced is likely to disadvantage women and contribute to the gender pay gap. Inconsistent applicant packs, Job Descriptors and Person Specifications were unanticipated findings suggesting a ‘cottage industry’ approach to recruitment and more likely to disadvantage female applicants. Most Person Specifications were unrealistic (73.1% listed ≥30 criteria) and ambiguous (15% did not specify Essential/Desirable criteria; 49% did not indicate assessment method). Benefits that could attract female candidates were not prioritised (e.g. tax-free cycle-to-work schemes were promoted four times more than childcare schemes). Recommendations for gender-fair job design are discussed.