In recent years, research, society and industry recognize the need to transform the agri-food system towards sustainability. Within this process, sustainability experiments play a crucial role in transforming the structure, culture and practices. In literature, much attention is given to new business models, even if the transformation of conventional firms toward sustainability may offer opportunities to accelerate the transformation. Further acceleration could be achieved through collaboration of multiple actors across the agri-food system, but this calls for a systems approach. Therefore, we developed and applied a new sustainability experiment systems approach (SESA) consisting of an analytical framework that allows a reflective evaluation and cross-case analysis of multi-actor governance networks based on business and learning evaluation criteria. We performed a cross-case analysis of four agri-food sustainability experiments in Flanders to test and validate SESA. Hereby, the key factors of the success of collaboration and its performance were identified at the beginning of a sustainability experiment. Some of the key factors identified were risk sharing and the drivers to participate. We are convinced that these results may be used as an analytical tool for researchers, a tool to support and design new initiatives for policymakers, and a reflective tool for participating actors.