This study's goal was to explore how new learning cultures might capture the many new needs of the retail industry sector and how apprentices can be trained for future work. Due to the inductive nature of this study, we found a rather implicit but important role of vocational education and training in retail that promotes the social advancement of apprentices with diverse social backgrounds. The narratives of 45 interviews with various actors involved in workplace training in one of the largest Swiss retail company revealed (1) how low-threshold and equitable access to training enables participatory engagement and self-determined success, (2) how trainers identify with social roles that are not explicitly required but are relevant for apprentices, and (3) how apprentices are given many opportunities during and after training to increase their social status. The study also revealed hindering factors such as the time and effort for the implementation of a new learning culture that affects all actors involved in workplace training. Second, are resistant negative social reproduction cycles and the heterogeneity of social backgrounds among the apprentices. Bridging this gap is simultaneously a goal and challenge for workplace training.