To effectively address the sustainability crises our planet faces, decision-makers at different levels of government worldwide will have to get a handle on three key challenges: learning from Global North and South initiatives in tandem, taking stock of social innovations alongside technological fixes, and nurturing grassroots sustainable development initiatives next to, or in place of, top-down corporate and government interventions. Current scientific literature and grant-making institutions have often reinforced the compartmentalized fashion in which we learn and draw policy lessons from North/South, social/technical, and bottom-up/top-down sustainability initiatives, including local food system innovations. The strategic levers for global sustainable development lying in-between are thus left out. This paper uses exploratory, multiple case study analysis to address this omission. By concurrently drawing lessons from grassroots innovations in Brazil, New York, and Senegal—three profoundly different socioeconomic and geographic contexts—we identify common pressure points that have enabled local communities to drive system-wide transformations toward climate adaptation, resilience, and sustainability in the agri-food system. The findings of this paper would be of value to scholars, government officials, and community groups engaged in agri-food systems sustainability and interested in the processes of change that have allowed budding innovations to stabilize and scale up.