Web-based learning has been developed by the majority of academic institutions and organizations worldwide due to its obvious benefits for both educators and learners. Meanwhile, many of the existing developmental approaches in this sphere lack one crucial consideration necessary for implementing web-based learning at academic institutions. In this article, the authors identify two processes: development of distance learning and digitalization of training that are represented now at almost every academic university. The article singles out the stages of their development and shows that the processes lead to the same result - a new quality of education. The authors focus on figuring out which path is more effective for achieving the highest level of development depending on university's characteristics. Accumulation of detailed information in the Electronic informational educational environment about current learning outcomes creates opportunities for emerging trends, such as Learning Analytics, Personalized Learning and Adaptive Learning. In data analysis using BigData and Machine Learning technologies.