Although a full autonomous manufacturing empowered by AI and Robotics technologies may yet be a achieved, a digital smart manufacturing is becoming quickly a reality. Among the several initiatives that fall under the umbrella of the digital smart manufacturing we find: the digital thread, the digital twin and the digital supply chain. This paper focuses on the digital supply chain initiative. This initiative, which leverages the most advanced technologies of Big Data, Machine Learning/Artificial Intelligence and IoT, will be probably the initiative with the largest impact cross all industries. While a supply chain management system driven by ML/AI and fully autonomous will be probably the moon shot of each digital supply chain initiative, within each company this initiative will be a journey through different maturity stages. In this presentation we’ll characterize each maturity stage along different dimensions (business objectives, ML/AI empowered capabilities, typical use cases). Moreover, smart ML/AI models and algorithms, will not be enough for moving successfully through this journey. A stage-specific data, process, people and technology readiness will be required in each maturity stage. Finally, which is the best strategy to start this journey?