The aim of this study is to delineate the necessary steps for designing, planning, executing, and evaluating the organization of online brokerage events aimed at fostering cooperation and creating new opportunities for short food supply chains (SFSCs). In this study, we focus on SFSC among agri-food value chain actors in three Central and Eastern European countries: Lithuania, Latvia, and Poland. The online brokerage events titled “Let’s build our SFSC” were organized in March 2023 as part of the agroBRIDGES project, funded by the European Union’s Horizon 2020 Research and Innovation Program. Drawing upon the SFSC concept, these events were aimed at promoting business-to-business collaboration among agri-food producers, farmers, and other businesses within the supply chain, thereby bringing together various stakeholders in the local agri-food sector. 31 participants took place in the events, which were facilitated using the AI-powered matchmaking platform Brella. The successful organization and facilitation of online brokerage and networking events require a comprehensive understanding of dynamic marketing capabilities. Critical components of such capabilities in the discussed context included the design of the events’ agenda, selection of the relevant participants, application of the innovative promotion strategies, and ensuring the engagement of effective moderators. Feedback from participants across all three countries indicated a positive reception of the events, highlighting the need for more frequent interactions. At the same time, due to significant variations in the digital proficiency among participants, such interactions should be organized via less complex, easy-to-use platforms.