Building deep, strategic supplier relationships has come to the forefront of companies’ goals in recent years. There are many different strategic sourcing methodologies available to procurement professionals. However, there is a gap in identifying the reasons and motivations as to why companies develop their suppliers, and how suppliers are developed in different business environments and contexts. To address this question, this study used semi-structured interviewing in support of a cross-case comparison approach. Analyzing the similarities and differences between modern businesses and how their sourcing decisions are made is crucial to better understand the motivations for developing suppliers. It was found that many companies have similar goals when investing in supplier health, but that the sourcing approach might differ based on age and size of the business, along with the stage of growth the business is in. This research shows that there is no “one method fits all” when it comes to strategic sourcing. The strategy needs to be more tailored to the current business needs and goals.