At the state of the art, both in information systems and (media) management studies, there is still few researches which investigate how newspaper companies organize their activities in order to manage the critical developments challenging their organisations through the digitalization of news distribution). In order to explore these issue, in this paper we first consider how the adaptation to convergence and information growth can be managed in newspaper companies undergoing reorganization to embrace technological innovation and alignment to the environment. Besides the adaptive cycle, indeed, we also consider how organizations align the adopted strategy to operations and in particular to the current information technology infrastructure and how it enhance (internalexternal) user innovation In particular, we discuss these issues in a pilot case study carried out at Corriere della sera, one of the main Italian newspaper. The aim of the research at Corriere della Sera is to understand how a major national newspaper organization manages the integration between activities related to the print newspaper and at the same time opportunities enabled by Information and Communication Technologies (ICTs) as well as by networks, social media and mobiles technology. Besides how the aim of the research is also to provide evidence of why the strategy is linked to organizational structure as well as information management configurations.