This study investigated whether the facial expressions of chief executive officers (CEOs) are associated with corporate performance. A photograph of the CEO or president of each company that appeared on the Fortune Global 500 list for 2018 was taken from the company’s official website. The smile intensity and action unit activation in each face were calculated using a pre-trained machine learning algorithm, FACET. The results revealed a positive association between smile intensity and company profit, even when controlling for the company’s geographic location (Western culture versus others) and the CEO’s gender. Furthermore, when the type of smile was examined with the activation of each action unit, this significant positive association was identified in the dominant smile but not in the reward and affiliative smiles. Relationships among the leader’s smile intensity, group strategy, and group performance are discussed.