Managing a digital product company in 2010, and beyond, is a very unique and challenging experience when compared to the traditional product development and deployment models of the late 20th century taught in many MBA schools today. This chapter presents the benefits, challenges, and lessons learned of a CEO who is transforming a traditional “Software as a Product” engineering software firm that he founded in the mid 1980‘s to a Web-based, “Software as a Service” firm that is positioned for 2010 and beyond.