The company analysed operates in the shipping and logistics industry. It has been steadily investing in its IT division to boost the digital transformation process and keep on being a reference point for the industry. This long journey requires to move from consolidated processes and traditional tools to digital platforms and sophisticated algorithms. The final objective is to increase efficiency, improve the monitoring of the processes and collect high quality data to implement more advanced solutions. However, the transition cannot be completed from morning to night. Indeed, to translate the existing processes, it is necessary to deal with several factors that imply notable levels of uncertainty, complexity and an overall high degree of risk.