The software development process is continuously changing, there is huge pressure to condense release cycles into shorter and shorter timeframes, tools are changing dramatically and companies must continually examine the efficacy of their development process. Attempting to hit a moving target is difficult and it is a decision which can have a major effect in terms of both the end-product and the business. In this paper, we discuss the role of situational context in deciding upon the software development process through the analysis of two case studies. The case studies take a detailed look at the organisational profile and context of each company in turn before we compare and contrast each situational context for factors that may influence the development process. We then compare the processes each company has chosen before our discussion of the role context plays in choosing a ‘correct’ software development process. While both companies have enjoyed sustained business growth and while both are agile in mind-set, we find that they are in fact quite distinct in their processes, this distinction being driven by their different situational contexts.