The paper investigates the potential axes and dimensions of roadmaps for digital business innovation for entrepreneurs as well as enterprises. Actually, digital business innovation requires a change of perspective with regard to IT governance and management of IT infrastructure. This is due to the need to adapt them to the constant evolution and changes in business models, consequent to the digitalization of company products and services. Also, the paper considers the business models fitting the diverse roadmaps showing their mapping to a company value chain. Finally, the paper discusses the characteristics of four key types of digital business organization “attitudes”, resulting from their orientation towards execution or else differentiation. The paper is based on insights and results from the FutureEnterprise project, which aims to deliver a research roadmap on new forms of internet-based enterprise innovation. The focus of the project is on what are defined there as “enterprises of the future”, that are driven by constant business model transformation and innovation, acting as multi-sided platforms built on - as well as emerging from - digital innovations at the global as well as local level to produce shared value including that beyond monetization.