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Today, companies face increasing market dynamics, rapidly evolving technologies, and rapid changes in customer behavior. Traditional approaches to product development typically fail in such environments and require companies to transform their often feature-driven mindset into a product-led mindset. A promising first step on the way to a product-led company is a better understanding of how product planning can be adapted to the requirements of an increasingly dynamic and uncertain market environment in the sense of product roadmapping. The authors developed the DEEP product roadmap assessment tool to help companies evaluate their current product roadmap practices and identify appropriate actions to transition to a more product-led company. Objective: The goal of this paper is to gain insight into the applicability and usefulness of version 1.1 of the DEEP model. In addition, the benefits, and implications of using the DEEP model in corporate contexts will be explored. Method: We conducted a multiple case study in which participants were observed using the DEEP model. We then interviewed each participant to understand their perceptions of the DEEP model. In addition, we conducted interviews with each company's product management department to learn how the application of the DEEP model influenced their attitudes toward product roadmapping. Results: The study showed that by applying the DEEP model, participants better understood which artifacts and methods were critical to product roadmapping success in a dynamic and uncertain market environment. In addition, the application of the DEEP model helped convince management and other stakeholders of the need to change current product roadmapping practices. The application also proved to be a suitable starting point for the transformation in the participating companies.