With growing popularity of social networks and online brand engagement, small and medium-sized enterprises (SME) are facing challenges in leveraging business value effectively from interactions with their online communities. Social listening tools, enhanced by artificial intelligence (AI), help enterprises to better understand customer needs and trends by synthesizing engagement and interaction data from various channels into actionable insights. However, prevalent tools widely appear too costly, inaccessible and complex to handle for SME managers. In response, we present this article on the design of “aiSnoop”, an AI-assisted social listening tool for SME managers. The article describes how the tool was developed, demonstrated and evaluated as a design artifact with an SME-contextualized design science research approach. We find that automation, usability and transparency, and advanced AI integration are important social listening tool capabilities for SMEs, contributing to the broader discussion on AI-assisted decision-support system design from an SME- and practice-oriented research perspective.