This study examines the roles of thinking styles, role ambiguity, and knowledge in predicting salesperson creative selling behaviors. It also examines the importance of salesperson industry knowledge (i.e., an understanding of the industry's regulatory environment) and salesperson organizational knowledge (i.e., an understanding of customers' internal political environment) in the creative selling–sales performance relationship. Survey data come from 262 business-to-business benefits broker salespeople to test the conceptual model. The results of the structural equations modeling confirm that a judicial thinking style has a positive effect on creative selling and that role ambiguity and organizational knowledge are also important antecedents of creative selling. Importantly, the analysis confirms that industry and organizational knowledge moderate the creative selling–sales performance relationship.