Courier, express, and parcel (CEP) services represent one of the most challenging and dynamic sectors of the logistics industry. Companies of this sector must solve several challenges to keep up with the rapid changes in the market. In this context, the introduction of autonomous delivery using self-driving trucks might be an appropriate solution to overcome the problems that the industry is facing today. This paper investigates if the introduction of autonomous trucks would be feasible for deliveries in urban areas from the experts’ point of view. Furthermore, the potential advantages of such autonomous vehicles were highlighted and compared to traditional delivery methods. At the same time, barriers that could slow down or hinder such an implementation were also discovered by conducting semi-structured interviews with experts from the field. The results show that CEP companies are interested in innovative logistics solutions such as autonomous vans, especially when it comes to business-to-consumer (B2C) activities. Most of the experts acknowledge the benefits that self-driving vans could bring once on the market. Despite that, there are still some difficulties that need to be solved before actual implementation. If this type of vehicle will become the sector’s disruptor is yet to be seen.