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The transition towards Servitization in the IT Business is extremely challenging because IT Enterprises must transform partly or entirely from hardware manufacturers into service providers. Moreover, Servitization does not occur all at once; it is a long and continuous process. Thus, in order to succeed, a company must determine which phase of this process it is in within a short time period, due to the dynamic competition in the modern IT Business. An examination of such a transition is crucial for accurate enterprise resource planning and for business success in general. Accordingly, to gain a better understanding of this process/transition in the IT industry, five major players were analyzed. We provide a foundation of the definitions and concepts regarding Servitization. Based on this foundation, every major player is analyzed by business segment. Then, those business segments are broken down into the offerings delivered to the customers. Depending on the offering, an analysis of the revenue is performed. In addition, we discuss the challenges and their effects on every company, and then we examine the similarities and differences in the process. We conclude with a brief statement of our primary achievements, and possible future investigation directions/topics are suggested.