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Abstract Scholarship is growing on societal transitions, describing radical societal change involving multiple sectors and scales, and transformative governance, describing how public, private, and civil society actors use tools of policy to pursue this fundamental change, aiming to build resiliency and sustainability. Much of this literature has a systems‐level focus and does not closely examine how governance participants, working individually or collectively, can steer a jurisdiction toward or away from transformativeness. This paper offers a corrective, integrating policy entrepreneurship scholarship with transformative governance research to advance understanding of how human agency underpins societal change. Drawing on accounts from 50 interviewees across eight case studies of US cities grappling with flooding hazards, we show how policy entrepreneurship can boost the political and economic resources that city officials rely upon to help propel radical shifts towards greater social, economic, and environmental equity.