This chapter highlights the need for healthcare professionals to adjust to the changing landscape of healthcare that is rapidly becoming technology-dominated. Healthcare professionals (HCPs) can improve their digital health literacy through training, but training programs that address their needs are scarce or do not meet HCP’s specific needs or lack focus on the clinical realities. The TRANSiTION project addressed this need and designed training on digital skills for the health workforce focusing on the needs of clinical and non-clinical professionals (i.e., health managers) for cancer prevention, diagnosis, treatment, and survivorship. This chapter demonstrates how principles of Learning eXperience Design (LXD) were applied for curriculum development and how theory was introduced into practice to design learner-centered, goal-oriented modules that create cognitive dissonance, use the right technology to create an appropriately supported learning environment, constitute a creative solution to an important learning challenge and are engaging for learners through gamification and immersive virtual reality. This chapter uses the TRANSiTION project as a case study to demonstrate how the digital literacy of oncology healthcare professionals can be addressed.