The scope of this work is to adopt a qualitative method to investigate the true essence of the Digital Transformation and the impact this can have on market competitive dynamics, business models and new product developments. From an academic, scientific and theoretical perspective and from an empiric one, by observing and applying the lessons learned in practice. A State-of-the-Art for Digital Transformation Strategies is missing. Especially in the Aviation Industry and its MRO business unit. Hence, due to the novelty, interdisciplinarity and complexity of the problem faced, an a-priory method was impossible to identify and refer to. A “Digitalization Journey” war therefore adopted as a methodology to conduct the analysis.