Digital Transformation is shaping the global economy and it is dividing companies between Leaders and Laggers. This research is aimed at understanding Business Value as the main driver of such a transformation. Understanding how Business Value is defined and quantified in different companies could be considered a precondition for understanding why the spread between Digital Leaders and Digital Laggers is widening. The chosen domain is the European Manufacturing Enterprises because such industry is generally lagging behind when it comes to Digital Transformation, while the chosen methodological approach is the qualitative one. The research provides (1) insights around the ways Business Value is defined on new Digital Transformation initiatives and how it is quantified before and after its deployment. We discovered that Business value monitoring and quantifications are not frequent due to two main factors: the fear of making wrong predictions and because of the increasing velocity in which the Digital Transformation process is taking place. The second research question is aimed at understanding (2) if it is possible to establish a correlation between the clarity and agreement over the definition of Business Value among the different stakeholders, and the perceived success of the initiative. The answer was negative, but admittedly, not definitive. While answering the third research question, the dissertation offers insights over (3) the perceived role of IT in Digital Transformation projects. The initial hypothesis, largely based on the Agile literature, that the IT should be considered a Business Value co-creator, was largely disproved by the interviewee who defined IT as a mere recipient of requirements coming from the business. The fourth research question (4) investigates which methodological approach should companies use to analyze Business Value and its delivery. Three methodologies were investigated and an agnostic approach was preferred given its more comprehensive (strategy, risk, cost efficiency, revenue) and prescriptive nature (it suggests a number of alternatives to quantify Business Value based on the way it is defined).