Large-scale e-learning initiatives are increasingly becoming an important strategy for organization-wide competence development projects. Such ventures are often primarily motivated by an ambition to cut costs and reduce the time between the identification of an organizational need and the launch of the educational initiative that addresses that need. However, there is a growing body of research that identifies several problems and obstaclesattacted to work-integrated e-learning. This paper reports from a large-scale e-learning initiative where a nation wide project was launched to address the challenges raised by geographical information systems to the public administrations of Sweden. The analysis identifies two interrelated challenges for large scale e-learning projects: Heterogeneity of participant and the situated nature of practice. It is concluded that these challenges needs to be addressed with a techno-pedagogical design approach where technological and pedagogical aspects are closely integrated with the existing and the future work practices.