The majority of studies into recruitment to the headship role have focused on supply-side dynamics and teachers’ own accounts of the factors that (dis)incentivize them from aspiring or progressing to headship. Significantly less work has been done in analyzing demand-side factors. This paper addresses the gap by presenting findings from a mixed-methods analysis of headteacher job descriptions (n = 67) published in a complete school year within Wales–one of the UK’s devolved education systems. A discourse analysis was conducted, based on organizational and occupational conceptions of professional work, which informed a subsequent content analysis of the job descriptions. Our findings identified a dominance of articulations that privileged organizationally-orientated understandings of headship and evidence of a lack of contextualization and agency by stakeholders responsible for recruitment. Such ‘demand-side’ analysis offers scope for examining and understanding the way in which headship is framed and aligns with policy within a variety of international educational contexts and jurisdictions.