In the CDIO ecosystem at Singapore Polytechnic, technicians serve as a critical bridge between academic instruction and hands-on student learning, embodying an essential but often under-recognized role in education. While technicians play a pivotal role in delivering and supporting learning, many view themselves as lacking expertise in teaching and learning compared to lecturers, resulting in a diminished sense of professional identity. To address this gap, we propose a novel approach to professional development tailored for technicians: a personalized, on-demand chatbot that supports continuous, situated learning aligned with their daily responsibilities. The chatbot was developed based on the “5 Moments of Need” theoretical framework, a model that posits five essential moments when learning is most impactful. This framework allows the chatbot to serve as a just-in-time learning resource that technicians can access anywhere and anytime. By leveraging this model, the chatbot is designed to deliver targeted content, formative assessments, and personalized feedback. To test the effectiveness of this approach, a prototype chatbot was introduced to a select group of technicians, providing them with on-demand, personalized learning experiences tailored to their specific needs within the CDIO framework. Initial feedback and usage data indicate that this chatbot has the potential to significantly increase engagement, bolster technicians' confidence in their instructional roles, and accelerate the acquisition of relevant skills. This paper will discuss the potential improvements for enhancing the chatbot’s capabilities. The broader implications of this personalized learning tool for the global CDIO community are substantial, offering a scalable, sustainable, and flexible solution that allows technicians to upskill efficiently within their professional environment.