This chapter first describes challenges that software companies face in making a strong business case to prospective customers. These include a history of solutions falling short of projected business case expectations, the customer’s unique perspective of costs and the difficult issue of technology adoption. Secondly, a process for building the software company’s business case in the new era is discussed. The process uses strategic frameworks to estimate and validate strategic objectives. Lastly, we look at a case study of e-docs that developed a unique way to manage unpredictable technology adoption.