One of the many initiatives within Louisiana State University's (LSU) holistic Communication across the Curriculum program is the LSU Distinguished Communicator (DC) Medal program. Implemented in 2005, the program encompasses communication experiences including mentoring, in-depth training in communication in their coursework, and practice of communication in leadership positions. Finally, students who earn the medal complete the DC ePortfolio as a summative, multimodal demonstration of their ability to effectively communicate who they are, what they are capable of, and how their experiences inside and outside the classroom are relevant to their post-graduation goals. To help students reflect, frame, and integrate their disciplinary learning with intention, DC candidates complete a series of exercises fostering metacognition, audience analysis, and inquiry about effective modes and technologies given their goals and related context. In this study, we explore development of the DC ePortfolio process over an eighteen-year period, focusing on three reflective questions inspired by our programmatic goals: How might the changes in the program over time increase focus on higher-order concerns? How do the changes support a student-centered practice? How does the DC ePortfolio process, both then and now, facilitate integrative reflection that will instigate transferable skills? As we continued to dive into this work, another question arose that speaks to the role of ePortfolios at a broader institutional level: how has our history of administering an ePortfolio program reflected our increasing understanding of the challenges and opportunities that emerge when balancing small-scale program-level learning goals with institution-wide large-scale metrics for learning? We submit that the DC ePortfolio process in its current iteration is a highly effective, small-in-scale model that positions students to combine reflective practices, classic approaches to audience analysis, and opportunities for extreme customization that multimodal technologies allow. This, in turn, supports students as they foster self-efficacy and develop a narrative that is not bound to templated or academic standards, but to customized goals and contexts that are constantly evolving in a dynamic world.