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Cloud systems have shifted traditional on-premise software products towards new and service oriented solutions. In order to adapt to this new trend, traditional software vendors are facing a necessary evolution towards service oriented software products. This software evolution is quite complex and full of problems. This paper presents lessons learned and the issues that emerged in a project aimed to adapt Meta 4' PeopleNet solution to adopt a cloud computing approach. This project, designed as a two-step approach, presents a set of issues that are analyzed in this paper, namely: Software evolution, Software processes and Technology and Personnel issues. The resultant conclusions, that highlight the importance of people in this software evolution, are useful for companies facing a product evolution process towards cloud oriented environments.