This paper investigates the importance of organization modeling in the study of information systems design and construction. Specifically, we emphasize the role of a suitable architecture in the development of an organization’s information systems (IS) supporting the specific mission of today’s electronic organization (e-Organization). The paper describes our architectural initiatives to substantiate IS education in terms of expositing the architectural way to support the design and construction of appropriate IS’s continually evolving over selected business domains. To realize the various IS services in an organization, whose activities are increasingly being virtualized (Web-enabled) over the Internet, we also introduce the idea of virtual-organizing the respective e-Organization initiatives. The paper emphasizes the importance of developing IS services not from the limitations of current technologies, but from the reality of fulfilling organizational goals. Thereby, we present our evaluation underlying the chosen pedagogical context of IS study in support of the argument that it is important to involve organizational concerns to steer the IS-efforts in electronically transforming (e-Transformation) the organization.