Teachers have been called upon to be more entrepreneurial in their approaches to change. However, the universities in which preservice teachers learn and the schools in which teachers practice tend to emphasize standards, accountability, and risk-management, while traditional entrepreneurial conceptions of innovation tend to promote risk-taking and the pursuit of disruptive change. In this interpretive qualitative study, the authors conducted semistructured interviews of 14 teachers, entrepreneurs, and teachers-turned-entrepreneurs, analyzing how they position themselves in terms of guiding interests, approaches to change-making, and orientations to power and the educational status quo. Findings revealed that innovators in schools must often work subversively and in an oppositional manner to make change. Teachers must position themselves beyond traditional roles as managers, consumers, and rote implementers of technology in preference of more creative and agentic modes of innovational leadership. Considering their critical emic perspectives, their professional ethic of care and their authority of expertise, the authors suggest that teachers could be developed as uniquely trustworthy agents of calculated risk-taking in change-resistant schools. They highlight measures that could be taken to better prepare and support them as critical innovators with technology, and draw implications for teacher education.