This paper will examine the importance of big data tools and digital technology for organizational design. Drawing on principles of cybernetics, particularly Ashby’s law of requisite variety and Beer’s Viable System Model (VSM), it will examine the potential implications of big data and digital developments for whether organizations need to be more centralized, decentralized or adopt networked arrangements with different level of stability and flexibility. The premise of the paper is that, for systems (such as organizations or collaborative networks) to remain viable, their internal complexity needs to reflect that of the environments in which they are based. Examples are provided from the case of the network agreement framework in Italy, which are analyzed using VSM as a theoretical framework.