The relationship between physical activity and educational and health outcomes is well known. As the significance of digital devices continues to increase, along with societal reliance on them, the provision of programs that draw technology and physical activity together is increasingly important. The recent Pokemon phenomenon is an example of a digitally-driven physical activity that appealed to both adults and children alike. This paper reports on the proof of concept phase of a development that brings to digital life a physical activity program designed specifically for preschoolers. The aim of the JumpStart project was to find a way to engage more parents with their children in physical activity. The brief from the customer was to ensure that the app was appealing to both parent and child with the view to creating a double motivation (push from the child and the parent). It was found through the design process that it was important for the application to appeal to both the child and their significant adult who would be an active participant in explaining and teaching the various skills. The proof of concept phase was introduced to a small group of child users. Informal feedback was collected to inform the completion of the proof of concept. Through the feedback, refinement of the design characteristics was uncovered which allowed a more comprehensive specification to be developed. Based on this proof of concept, the full application is now in development, continuing to explore the connection between co-location and collaboration in digital game design for preschoolers in a more comprehensive research study.