Cross-selling is one of the most important sales strategies retail organizations adopted to drive business revenue and increase customer lifetime value. While considerable efforts have been devoted to developing data-based cross-selling models, little is known about how and when store managers can drive frontline service employees (FSEs) to cross-sell. Drawing on work meaningfulness literature, we propose that a high-quality resource exchange relationship with the store manager (i.e., leader–member exchange, LMX) endows FSEs’ work with meaningfulness of serving others, which in turn promotes their engagement in cross-selling. We further contend that when store managers possess high person-organization fit, the impact of their LMX relationships on FSEs’ work meaningfulness of serving others and subsequent cross-selling would be stronger. A three-wave survey data from 166 FSEs and their store managers in a retail chain in China (i.e., Study 1) and an experiment among 120 U.S.-based working employees (i.e., Study 2) support our predictions. The present research offers important theoretical and practical implications for retailing management area.