Education has been restructured in many Western post-industrial nation states during the 1990s. The Australian Technical and Further Education sector (TAFE) has been particularly susceptible to discourses of responsiveness to the market and the new entrepreneuralism. This article explores how women have been repositioned in contradictory and ambiguous ways as the new entrepreneurial middle managers by existing and emergent discourses that circulated in and through TAFE organizations. In turn, it points to how discourses of change management and client responsiveness took on particular readings within specific institutional and professional cultures of the eight Technical and Further Education institutions (TAFEs). At the same time, the restructuring that arose from the corporatization of TAFE, in a highly gendered process, through the twin strategies of marketization and the new managerialism produced new possibilities for individual women educators who moved up into middle management. Yet these individual women were positioned within highly masculinist ‘neo-corporate bureaucratic cultures’ that co-opted their passion for the capacity of education to make a difference and incorporated these new entrepeneurial work identities.