Using humor wisely is known to have many benefits in a work-related setting. Despite these potential benefits, there is limited research on this phenomenon in a business-to-business selling context. In light of this absence, the authors introduce a theoretical model explaining the role of humor usage in a salesperson-customer encounter. Specifically, the purpose of this paper is to examine the simultaneous influence of salesperson humor usage on creativity and customer trust, which in turn affect objective sales performance. Using 149 salesperson-customer dyads from a cross-industry survey, the results indicate that (1) salesperson humor usage positively influences salesperson creativity and customer trust, (2) which in turn mediates the influence of humor on objective sales performance. In addition, (3) customer trust also influences word-of-mouth propensity and expectation of relationship continuity. The article's broader contribution is that humor usage may be a fundamental human ability that is central for enhancing creativity and developing strong relationships in a business-to-business setting.