Adaptive selling and customer orientation have been considered imperative for successful salespeople. Although these topics have been frequently studied in the literature, most studies have been conducted in a developed country environment and such studies are limited in other cultural contexts. Moreover, cross-country/cultural comparison of the role of adaptive selling and customer orientation is even scarcer. Therefore, the objective of the current study is to examine the role of adaptive selling and customer orientation on salesperson performance in two distinct markets of Europe and Asia—namely Finland and Macau. Using personal interviews, data were collected from salespeople operating in both countries. The study results indicate that customer orientation had significant effect on sales performance, customer satisfaction, and adaptive selling behavior of salespersons. Furthermore, salesperson adaptive selling behavior had significant effect on sales performance and customer orientation but not on customer satisfaction.