Lifelong vocational learning in a digital context frequently falters due to a lack of motivation, structure, time management, and attention to adult students’ work-life balance. In remote settings, students have further little contact with peers and feel disconnected. This paper answers how a Virtual Learning Companion (VLC) can be designed to address these challenges and fulfill the specific needs of vocational students. Following a Design Science Research (DSR) approach, a meta-requirement mapping process combines insights from a literature review and ten semi-structured interviews with vocational students. A focus group with experts from the field of vocational training, online learning, chatbot design, and DSR evaluated the results. As a result, five Design Principles are presented: (1) Motivational Goal Setting, (2) Context and Learner Adaptation, (3) Focus and Control, (4) Promoting Resilience, and (5) Enabling Social Interactions and Feedback. Exemplary Design Features further illustrate the VLC development.