This paper is written from the perspective of an Anglican head teacher in the context of UK public educational policy in which managerialism is construed as the prevalent orthodoxy of reform. It seeks to bring the discipline of theology and the field of school leadership studies into closer dialogue around the theme of managerialism in a way that will benefit academic scholarship and practitioner researchers. Firstly, it explores "The Way Ahead" report as an impetus to critical theological reflection about Christian vocation and the distinctive role of church school head teachers. Secondly, it indicates how the site of managed reality is important for theology and how the theology of education might be pursued in defence of education. Against claims that "doing" theology tends to domesticate education, it is argued that theology can help provide an important countercultural perspective intended for the good of education. Thirdly, it outlines the background of public educational policy which makes countercultural theology an appropriate response in the service of a faith-inspired professionalism. Fourthly, it suggests how a countercultural model of contextual theology can collaborate with important forms of research in the field of educational leadership, management and administration.