The Gutenberg Technology Course Management System (CMS) presents onboarding challenges for new authors, particularly during the early project setup flow and when learning how to add and organize content. Our team conducted nine moderated usability tests with Tobii eye-tracking software to identify key mismatches between how users expected to set up and build projects and how the current CMS workflows were structured. From these insights, the team designed evidence-based recommendations and high-fidelity mockups to improve clarity, reduce onboarding friction, and support a smoother, more intuitive authoring experience.