Meeting today's prospective college students where they are is key to staying ahead of current enrollment challenges. Understanding which messages resonate with which students and at certain parts of the enrollment funnel helps to ensure institutions are getting the right message, to the right student, at the right time in their journey. By utilizing a MaxDiff approach, one can better understand the impact a particular message has compared to others and which combination of messages will ultimately drive action. The maximum difference scaling (MaxDiff) method provides useful guidance on how enrollment professionals can better segment their communication strategies to their multiple constituents. While affordability messages are most impactful, especially to parents, prestige and employability were well received by already-admitted students. Further differences between key segments emerged from the data, creating a better understanding of how to inform strategic initiatives. The messaging preferences of additional groups, however, remain to be explored, such as graduate students, adult learners, international students, alumni, and other segments that are important for institutions that are building and refining their strategic enrollment plans. This article provides a framework on how institutions can better optimize their messaging to maximize impact in the student enrollment journey.