Software development is a knowledge intensive activity involving the integration of diverse knowledge sources that undergo constant change. Most approaches to knowledge management assume that information exists and is readily sought by software developers, usually through a search tool. In this paper, an approach is presented that actively delivers information through a rule-based system that matches system requirements to experience-based knowledge embedded in work breakdown structures. A reuse-based methodology based on an organizational learning process is used to capture and organize knowledge as it is created. The combination of tool and methodology work together to capture characteristics of individual projects and tailor processes to meet diverse and emerging software development needs. The tool and methodology are demonstrated using two examples of how this technique can be applied.