With the rise of the internet, mobile technologies, and, most crucially, e-commerce, the retail industry has changed dramatically in recent decades. Emerging digital technologies, such as information and automation, have recently made it feasible for even more types of retail business to exist. One of the key strategic themes for retail businesses in Europe, and indeed the entire world, is the digital transformation of the supply chain. However, many retail representatives have only a vague idea of the exact steps that need to be taken in the digital arena. The retail supply chain does not seem to know how to measure the actual level of its digitalisation, and it is not clear whether the current digital development of the supply chain is on a good track, thus lacking guidelines for further strategy development and investment. Previous studies have shown that Maturity Model (MM) helps enable retail companies assess their level of digitization. On the one hand, MM can help companies assess the gap between themselves and competitive benchmarks. On the other hand, it can help managers to have a more comprehensive and scientific understanding of the current digital performance of their companies. MM is a great tool for both comparison with competitors and internal optimization of companies. All in all, using MM not only helps to position an existing relationship on the maturity scale but also helps to identify areas where improvement is needed to achieve a higher maturity.