On the one hand, the increasing digitalization of commerce has put local owner operated retail outlets (LOOROs) under pressure to adapt their business models to the new technological and competitive environment as well as to the changing shopping habits of their customers. On the other hand, it also offers potential competitive advantages for them. This paper investigates the retailers’ perception of the competition and their perception of customer expectations, combined with a survey of the current use of digitalized services and the LOOROs readiness to increase the usage of digitalized services. Our results confirm that the perception of competitive pressure and customer expectations has a positive influence on LOOROs’ readiness to adopt new technologies and business models. But a significant number of the surveyed retailers underestimate the expectations of their customers and are reluctant to add digital services to their business portfolio. While our key findings are relevant insights for all LOOROs on their journey towards digitalization, our findings provide even more significant insights for all digital service providers aiming to take a slice of the still substantial market shares of LOOROs in rural areas.