Data collection and analysis (DCA) skills apply mathematical knowledge, such as counting, sorting, and classifying, to investigations of real-world questions. This pursuit lays the foundation for learners to develop flexible problem-solving skills with data. This pilot study tested a preschool intervention intended to support teachers in promoting young children's DCA skills using a technology-integrated approach. A key component therein was a teacher-facing digital app that facilitated collaboration between preschool teachers and children to more easily collect data, create simple graphs, and use graphed data to engage in real-world questions and discussions. As part of a design-based research approach, this study tested the intervention's developmental appropriateness and feasibility in four preschool classrooms (n = 5). Findings suggest that the intervention curriculum (i.e., investigations) and inclusion of the app supported teachers and children to answer data-focused questions by engaging in each step of the DCA process while applying numerous mathematics skills. Teachers reported that the app complemented curricular implementation and children demonstrated readiness to engage with, and benefit from, the investigations. Findings also indicated the developmental appropriateness and feasibility of applying this DCA approach in preschools and suggest further study of the approach.