Industry 4.0 and Smart Maintenance represent a great opportunity to make manufacturing and maintenance more effective, safer, and reliable. However, they also represent massive change and corresponding challenges for industrial companies, as many different options and starting points have to be weighed and the individual right paths for achieving Smart Maintenance need to be identified. In our paper, we describe our approach to evaluating maintenance organizations in a case study for the oil and gas industry, developing a shared vision for the future, and deriving economical and effective measures. We will demonstrate our approach, by showcasing a specific example from the oil and gas industry, where a need for action on HSE-relevant critical flanges in the company's piping systems was identified. We describe the steps, that were taken to identify the need for action, the specifications of the project and the criticality analysis of the piping system. This resulted in the derivation of a digitalization measure for critical flanges, which was first commercially analyzed and then the flanges were equipped with a continuous monitoring solution. Finally, a conclusion is drawn on the performed procedure and the achieved improvements.