Goal of the research presented in this paper is to generate an expertise document analyzing the potential of a document and workflow management system (DMS/WMS) for a specific customer. Addressee of the expertise is on the one hand the possible client who receives decision support for the investment decision in the DMS/WMS (like the expected ROI, quantitative and qualitative benefits, or potential risks), and on the other hand the software vendor himself who obtains detailed technical information about the potential project (achievable contribution margin, technical problems in similar projects, or code snippets used in comparable situations). Moreover, the paper presents the relevant part of the corresponding business process of a vendor of DMS/WMS, a description of the deficits of the current sales staff to analyze the potential of complex software systems (focus on DMS/WMS), and a concept together with a prototypical implementation of an expertise system. Since in a project-oriented distribution of a DMS/WMS many pieces of internal and external knowledge can be useful, the design of an ontology of the domain DMS/WMS which is realized in form of a Semantic Network is described. This domain knowledge serves as a means to store experiences, e.g. from past projects. Additionally, a rule base is presented in order to process business rules.