Digital technologies can reinvent the higher education in 21st century. E-learning introduces change to both the people and the organization on any scale. To keep abreast of the times and making learning fun, one of the self-financed Higher Education Sector in Hong Kong introduced Virtual Reality (VR) and online learning for aviation and healthcare courses. This paper explores the successful implementation of E-learning in one case study Higher Education sector in Hong Kong. The paper investigates the constraints which affect the successful implementation of E-learning in the sector. It also provides some strategies for academicians in development and implementation of E-learning. Educational leaders can strategically promote and enable E-learning at organizational and individual levels by using Peter Senge’s Five Disciplines of Learning Organization (1990). The keys to achieve a learning organization are personal mastery, mental model, shared vision, team learning and system thinking. These five disciplines support and sharpen one another, integrated by systems thinking.