Digital transformation strategies are of elementary importance for organizations competing in the digital age. Challenges such as faster changing customer needs, new value creation structures in digital eco-systems, or the use of collective intelligence to innovate business models require leveraging digital technologies. To achieve this and remain competitive, appropriate digital transformation strategies need to be in place. Yet, studies show that organizations struggle with strategy formulation and implementation. Based on workshops with practitioners the authors obtained concrete needs, pains, and gains as requirements for the development of an own, new intelligent and platform-based assessment tool. The proposed tool collects, calculates, and visualizes in a self-service manner, relevant company data to support decision-makers and organizations in digital transformation strategy development and implementation.