Digital transformation is vital for organizations in all sectors, as it changes value creation, customer relationships, and internal processes. A key concern in digital transformations is creating and executing an effective strategy that reimagines the organization. However, structured approaches for reimagination in a digital transformation are still missing. This paper contributes to this concern by reviewing how roadmapping is used in the digital transformation literature. Roadmapping is a flexible technique to support the strategic formulation of short-and long-range changes to software, business, organizational and structural aspects. Reviewing 28 papers on digital transformation, we uncovered five types of roadmapping for reimagining organizations: Product-Technology, Strategy, Business, Data, and Design. For these five types, we unfold the landscape of obstacles, opportunities, and context for different pathways to successfully reimagining organizations in digital transformations.