Video-based learning is widely used today in both formal education and informal learning in a variety of contexts. Videos are especially powerful for transferable skills learning (e.g. communicating, negotiating, collaborating), where contextualization in personal experience and ability to see different perspectives are crucial. With the ubiquity of widely available video content, video-based learning is seen as one of the main strategies to provide engaging learning environments. However, numerous studies show that to learn effectively while watching videos, students need to engage actively with video content. We have developed an active video watching platform (AVW-Space) to facilitate engagement with video content by providing means for constructive learning. The initial studies with AVW-Space on presentation skills show that only students who commented on videos and who rated comments written by their peers have improved their understanding of the target transferable skill. In order to foster deeper engagement, we designed a choice architecture and a set of nudges to encourage students to engage deeper. We conducted two studies investigating the effect of nudges. The results provide evidence that the initial set of implemented nudges is effective: the students who received nudges wrote more comments, used different aspects, and there were more students who wrote comments. The nudges were particularly helpful for undergraduate students who were less experienced in self-regulated learning. Future work includes designing additional nudges to enhance student engagement by improving the quality of comments and by encouraging participation in collaborative activities.