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This paper describes the theoretical and processual approaches used to design, develop, and run a pilot online non-formal Design Thinking-based learning programme for long-term unemployed postgraduates in Ireland – Grad2Work. The purpose of the programme was to provide a heterogenous cohort of participants with skills, methods, and strategies to navigate and successfully overcome challenges associated with re-entering the workforce after an extended period in unemployment. The programme design approach was informed by Social Constructivist learning theory ND Kulcsár et al’s Career Decision-Making Framework. A mixed method approach was used to gather quantitative and qualitative data from participants at the conclusion of the programme. Analysis of the data indicated that the pilot programme met its objective of preparing participants to progress their career ambitions. It is concluded that incorporating a Human Centred Design mindset, a robust decision-making framework, and Design Thinking processes provide a systematic approach to course design. Modern digital collaboration platforms adequately support efficacious teaching, learning, and collaboration. Seeking and applying participant insights and feedback into the course enhances opportunities for them to use the knowledge and skills acquired. Providing ongoing support for participants’ holistic life balance requirements during programme delivery is important for successful implementation. These conclusions will have applications in Design Thinking for Teaching and Learning, using process frameworks to support return-to-employment strategy formation, and transversal skills development for adult learners.