The emergence of Chief Executive Officers as leaders of educational service providers is positioned in multi academy trusts, the preferred structure of schooling in England. Within this structure, the Chief Executive Officer position is distinct and different from previous constructs of headteachers, since the Chief Executive operates at both street level, that is within the MAT, and beyond 'the street'. In this article, I argue that a new conceptualisation of the headteacher is needed to explain the emerging position and practices of the Chief Executive Officer. These include the interface with the market, adopting entrepreneurial dispositions and constructing professional and business networks. I typologise these practices and positioning through the analysis of empirical data gathered from the Leadership of the Lawrence Trust Project and its Chief Executive Officer, KT Edwards.