In a prospective study of 150 junior salespeople in the same company, we examined the relation between fearless dominance, which is a dimension of trait psychopathy, and objective performance in field sales. After controlling for demographic variables, length of job tenure, initial sales training quality, and disciplined achievement motivation, the results supported an inverted U‐shaped relation, which showed that, after a certain turning point, increases in fearless dominance resulted in decreases in performance. Thus, the most successful salespeople in our sample possessed moderate levels of fearless dominance. Implications for theory, practice, and future research are provided in light of a number of notable strengths and limitations.