In this research with reflection paper, we discuss our experiences from a graduate level service learning course in which we assisted the local food bank on exploring the efficiency of their client tracking software, Link2Feed. In the semester-long project, we developed a close relationship with the staff of the community partner and worked to explore functionality and usability (Johnson, Salvo, & Zoetewey, 2007; Johnson, 2010) of Link2Feed. Throughout the semester, we applied various academic skills like taking interviews, rhetorical analysis of the software, and analyzing the community partner needs and how the software meets those needs. At the end of the semester, we were able to provide a detailed report on the features of the Link2Feed and its embedded functions. We also found ways to address the current needs of the partner organization for big data collection, reporting, and visualization. With the framework of experience architecture (Potts & Salvo, 2017) and workplace-based writing and communication and composition with community, we discuss the challenges of negotiating the needs of the community partner, their infrastructural limitations (DeVoss, Cushman, & Grabill, 2005), and the use of academic research to enhance the community partner’s efficiency to generate big data and knowledge via digital technologies. In this paper, we also reflect on the overall process of conducting a semester-long service learning/ community engagement project and the challenges and benefits of negotiating community partner’s priorities, the challenges in investigating an unfamiliar software platform, and the importance of regular communication with the professor.