Research advances in the last decades have allowed the introduction of Internet of Things (IoT) concepts in several industrial application scenarios, leading to the so-called Industry 4.0 or Industrial IoT (IIoT). The Industry 4.0 has the ambition to revolutionize industry management and business processes, enhancing the productivity of manufacturing technologies through field data collection and analysis, thus creating real-time digital twins of industrial scenarios. Moreover, it is vital for companies to be as "smart" as possible and to adapt to the varying nature of the digital supply chains. This is possible by leveraging IoT in Industry 4.0 scenarios. In this paper, we describe the renovation process, guided by things2i s.r.l., a cross-disciplinary engineering-economic spin-off company of the University of Parma, which a real manufacturing industry is undergoing over consecutive phases spanning a few years. The first phase concerns the digitalization of the control quality process, specifically related to the company's production lines. The use of paper sheets containing different quality checks has been made smarter through the introduction of a digital, smart, and Web-based application, which is currently supporting operators and quality inspectors working on the supply chain through the use of smart devices. The second phase of the IIoT evolution-currently ongoing concerns both digitalization and optimization of the production planning activity, through an innovative Web-based planning tool. The changes introduced have led to significant advantages and improvement for the manufacturing company, in terms of: (i) impressive cost reduction; (ii) better products quality control; (iii) real-time detection and reaction to supply chain issues; (iv) significant reduction of the time spent in planning activity; and (v) resources employment optimization, thanks to the minimization of unproductive setup times on production lines. These two renovation phases represent a basis for possible future developments, such us the integration of sensor-based data on the operational status of production machines and the currently available warehouse supplies. In conclusion, the Industry 4.0-based ongoing digitization process guided by things2i allows to continuously collect heterogeneous Human-to-Things (H2T) data, which can be used to optimize the partner manufacturing company as a whole entity.