The digitalisation of educational communities has increased rapidly in the last decade. Modern technologies transform the way educational leaders such as teachers, tutors, deans and supervisors view and manage their educational communities. More often, educational leaders offer a variety of gateways, guiding the e-learners in their search for finding and understanding information. A new type of leader is required for understanding the needs and requirements of geographically dispersed e-learners. This calls for a compassioned kind of leader, able to reconcile the dilemma of high-tech versus hi-touch in the online classroom. This article examines servant-leadership and its implications for e-learning in the 24/7 classroom where community building is key.