Digital technologies have created new opportunities to enhance business processes and improve the performance of organizations. At the same time, digital technologies pose challenges for organizations as they are required to prepare for significant transformation of work associated with digital technologies. More specifically for entrepreneurships, digitalization is creating new opportunities that affect the organizational economic activities. It promotes decoupling between form and function, promotes disintermediation—reducing the power of middleman in value chains, and drives generativity—enabling the coordination of geographically dispersed parties and opening new ways to build organizational capabilities. However, it is currently unknown how digitalization shifts or couples with different elements of entrepreneurial ecosystems—namely skilled workers, work environment, and the existing systems within an organization to create new business values. This project uses a mixed method approach and tackles three critical questions (i) What are the elements of digitalization that facilitate or hinder innovation within an organization? (ii) How does digitalization change the entrepreneurial ecosystems (i.e., job characteristics, information sharing capability, work environment etc.)? and (iii) Under what conditions will digitalization complement already established organizational capabilities to advance innovation and organizational outcomes?