Manufacturers deem servitization a competitive remedy, facing heightened customer expectations and competition amidst their digital transformation. Servitization refers to a shift from offering products to offering digital product-service systems. Although previous research inquired about traditional service operations, research into the servitization’s digital nature remains nascent and insights addressing the behavioral changes associated with such transformations are lacking. This paper presents an ongoing case study at a German car manufacturer, sharing insights into which organizational and individual factors drive salespeople’s behaviors during servitization based on twelve interviews and eleven workshops. The analysis suggests that usage clarity is key to mediating behaviors. Organizational factors driving behaviors include information dissemination, service orientation, and formalization. Individual factors driving behaviors include technology affinity and involvement. The paper contributes to understanding salespeople’s behavioral changes during introduction of digital product-service systems. Recommendations on designing personnel training programs to improve the marketing of digital product-service systems are derived.