After the longest period of continuous growth in its history, the automotive industry is experiencing a most dramatic downturn. The challenge for automobile companies is not just to cope with the three converging trends of vehicle electrification, autonomous driving, and shared mobility, but also to make the best judgement on how and where to invest in a declining market. Digital is becoming the de facto way of operating along the value chain. Advanced automation, artificial intelligence (AI), and additive manufacturing will reshape traditional processes. This chapter reports upon the implementation of new digital technologies and related critical success factors in two multi-national industries, with major interests in the automotive sector. It takes an empirical approach, analysing use cases, projects, and input from experts. The findings assess the repercussions for IT strategy and changes in business processes impacted by the use of new technologies and illustrate how people skill requirements have evolved, both within the IT organisation and in other company departments.