Recently, new approaches to organizational level sustainability management and reporting have emerged in the form of software and web-based applications. At first glance, it appears that such software and web-tools are applicable in small and medium-sized enterprises (SMEs), as they offer user-friendly and cost-effective alternatives to assess, manage and report on company-wide sustainability activities. Nevertheless, it remains academically and practically uncertain if such technological advancements will be adopted by a great number of SMEs. Using the Individual-Technology-Organization-Environment (ITOE) model as a theoretical framework and empirical data from a recent survey with 1,250 German SMEs, this paper investigates various firm-internal and external factors that might influence managers’ decisions to adopt or reject this new technology. This paper reveals which factors might play a role in the adoption of such web-tools in SMEs. In addition, this paper proposes a conceptual framework of an IT-assisted sustainability analysis and reporting scheme for micro-enterprises and startups. Based on existing software for larger enterprises, the paper describes the main content and potential layout of such a web-based tool.