Digitalization changes both buying processes and sales processes and, consequently, the dynamics and division of work between buyers and suppliers in the supply chain. This has major implications for industrial marketing and supply chain management. In this study, we analyze the impact of sales configurators, which are used to create valid configurations of market offerings that fulfill customer requirements. The usefulness of sales configurators can be investigated from both the sellers' and buyers' perspectives. In this research, we focus on the latter, and we specifically investigate the antecedents of customers' acceptance of sales configurators in a supply chain. In our analysis, we concentrate on system-level antecedents, which have been neglected by the existing literature. Our research yields better knowledge of how digital sales technologies can be used by customers for improved effectiveness and perceived value. The results demonstrate that ease of use and system adaptability contribute strongly to the perceived effectiveness, and eventually to the perceived usefulness, of sales configurators. Yet, surprisingly, perceived enjoyment is identified as having the most significant effect on perceived usefulness.