This study explores the challenge of maintaining motivation in further education for working students, who face the double burden of work and learning. To address this issue, we investigate the design and implementation of a pedagogical conversational agent (PCA) within a web-based training (WBT) platform. Drawing on literature, interviews with 11 experts, and a creative workshop with 14 working students, we use the Hexad user type framework to tailor the WBT to each user’s motivational archetype. We prioritize design features for each of the six archetypes and instantiate these in a prototype. In a field experiment with 17 working students using the WBT prototype for exam preparation, we observe a significant increase in intrinsic and extrinsic motivation. This study contributes to the emerging field of PCA-enhanced digital learning, highlighting the potential of personalized motivation in persuasive dialogue systems.