This paper presents a new approach to Technology Roadmapping by integrating marketing and decision methodologies. While much of the research into technology roadmapping has been applied to products that represent a one-time ROI to the manufacturer, current Internet technologies are resulting in web services that use an entirely different financial and business model of licenses and subscriptions. This paper addresses the software services applicability and documents a start-to-finish application of cross-discipline models and tools to form a real-life roadmap from market drivers to project headcount. Pitfalls in the roadmapping process will be documented and suggestions for improvement will also be discussed. © 2009 Elsevier Inc. All rights reserved.