The educational landscape in Portugal encompasses a diverse array of non-degree courses, including executive training, lifelong learning courses, professional certifications, and specializations. These programs play a vital role in addressing the dynamic demands of a rapidly evolving labor market, providing individuals with opportunities to continuously develop skills, adapt to changing environments, and enhance their career prospects. However, a clear framework for informed and timely planning of curriculum changes is currently lacking, leading institutions to react to complaints of misalignment in their offerings. This study, part of a broader investigation aimed at establishing this framework, seeks to contribute to the understanding of contextual and social factors influencing executive education in the field of Digital Design in Portugal in recent years. A ten-year Portuguese case study was analyzed, incorporating questionnaire results, workshops with current and former students, and interviews with various academic stakeholders. Interviews with relevant public and private actors in the Portuguese market complemented the analysis. The crucial insights gathered lay the foundation for essential knowledge, informing the formulation of future educational strategies in the design of curricula for postgraduate courses in Interactive Digital Design. These insights could inform the creation of a comprehensive framework. The knowledge obtained serves as a valuable resource for institutions seeking to refine their educational offerings in response to evolving industry demands.