Higher Education Career Services Offices are often called upon to serve more students than they are able to provide with meaningful, individualized job search support. Engaging alumni mentors to provide job search support to students is one way that career services offices have sought to increase the amount and quality of assistance students receive. Increasingly, institutions are utilizing online mentoring platforms to connect students and alumni mentors. A large, mid-Atlantic university recently began to develop its own online mentoring platform, which is scheduled to be launched to School of Education students in the fall 2020 term. This study evaluated that system to determine which features need to be improved prior to the launch. It was found that the system needs distinguishing characteristics, such as access to alumni, direct job search support, and increased job postings. Students will need to be oriented to the site and told how to navigate it. The system also needs to be promoted as a tool for job search support so that students use it as such and immediately understand why the site exists and how the site is to be used. Additionally, feedback must be given to platform administrators so that they can address system glitches and ensure that the site is appropriately populated with alumni who are available to assist students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]