Upswing provides an intelligent virtual assistant and student services platform to reach, relate to, and retain non-traditional students. They define non-traditional students largely as adult learners, first years, and online students. Backed by some of the biggest names in HigherEd, Upswing is driven by the mission to provide a personalized education journey for all of its learners and eliminate attrition. Through their customized engagement platform and virtual tech assistant - Anna - their student users can accurately and efficiently identify the right campus resources for any problem. An end-to-end distributed solution, Upswing instantly organizes a meeting between the appropriate campus resource and the student via SMS, which then takes place entirely on the platform. Coaching is also available 24/7 for students who are occupied outside of regular college hours, to break down barriers of remote learning. With a focus on retention, Upswing also logs every auto-message, session, feedback piece, etc. to share with their partner schools to help address why students might be dropping out. Upswing is changing the way colleges approach their non-traditional learners, a pool that is growing every year as remote work and distributed learning become the reality for so many.