Successful implementation of e-learning environments requires adequate teacher training. In this study, a solution is sought for how teacher training programmes on newly introduced Learning Management Systems (LMS) can be designed in such a way that they would be inclusive of different levels of digital competence, supportive of individual teacher development and flexible enough to be applied in different institutional environments. Following the soft design science research methodology, two co-creation and co-design sessions, as well as eight in-depth interviews, were used for designing and testing a model for the process of teacher training in using LMS. The outcome of the study indicated the need of an agile-based approach as well as two kinds of segmentation of the training process based on the level of competence and on the position of the training process on the timeline. Besides, the cascading of teacher training was found to be a key approach to make it cost- and time-efficient. Moreover, the introduction of agility to the recursive process of training was found to strengthen consistent knowledge building in teachers. This has been illustrated in the form of a spiral model of knowledge construction, with teachers beginning to learn the basics and incrementally progressing to acquire advanced skills. The proposed process model allows academic institutions to mobilize the teaching task force by equipping them with technological knowledge systematically. This way, the level of expertise in using LMS can be developed incrementally and in synergy with the Pyramid Model of Digital literacy. The level of knowledge acquisition by teachers would correspond to the levels in the pyramid, and thereby, it would be easy to see them “climb up” the pyramid as they progress. A more thorough evaluation of the model using different cases and a careful revision of its components are considered as further steps in this research.