Advising undergraduate students on how to succeed in their academics, careers, and life is one of the most common practices in higher education. Advising is also something that many institutions struggle to resource or coordinate sufficiently, due to hurdles such as overwhelming caseloads and limited interdepartmental communication, potentially leaving students without needed support on their paths to successful program completion. To help address student needs, many institutions turn to technology to support instructors, faculty advisors, primary-role advisors, and students engaged in the advising process. Technology can support various functions within the advising process, including managing caseloads, identifying students who may benefit from proactive outreach, and empowering students with more information about and control of their academic journey. Despite challenges, some institutions have found success in the implementation of advising technologies. While many factors can contribute to a successful implementation, the role that stakeholders play in that process has not been well understood. This research brief compares and contrasts the experiences of two institutions, Webster University and West Virginia State University (WVSU), in piloting a new advising technology. More information on this larger initiative can be found on Ithaka S+R's website.