Social selling is a prominent marketing strategy in this digitalization era. Thus, this research aims to inspect the moderating role of social media use in the relationship between selling skills (salesmanship, technical, active empathetic listening (AEL), and emotional intelligence (EI) skills) and selling behaviors (cross/up and adaptive selling behaviors). A sample of 185 respondents was collected from salespeople in Lebanon using a questionnaire, and data were analyzed with structural equation modeling (SEM) using AMOS graphics 24. The outcomes revealed that salesmanship, technical, AEL, and EI skills drive adaptive and cross/up-selling behaviors. In addition, social media use enhances the relationship between salespeople selling skills and behaviors. Finally, this research suggests key insights into the social selling context and offers guidelines to marketing managers on how to execute an effective social selling strategy.