This study explores the integration of Systems Engineering (SE) and Design Thinking (DT) to design a digital learning platform for Indonesian social entrepreneurs. It addresses the challenge of aligning technical system models with lived human experiences, embedding empathy and usability within functional design. By reimagining SE tools like ConOps and OPM within user-centered frameworks, the project bridges analytical rigor with human relevance. In line with the theme “Where Legacy Meets Future,” it presents a hybrid methodology that prepares emerging designers to navigate complex, systems-level design with both structure and sensitivity.