Every year in the United States, medical students and residency programs dedicate millions of dollars to the residency matching process. On-site interviews for training positions involve tremendous financial investment, and time spent detracts from educational pursuits and clinical responsibilities. Students are usually required to fund their own travel and accommodations, adding additional financial burdens to an already costly medical education. Similarly, residency programs allocate considerable funds to interview-day meals, tours, staffing, and social events. With the rapid onslaught of innovations and advancements in the field of telecommunication, technology has become ubiquitous in the practice of medicine. Internet applications have aided our ability to deliver appropriate, evidence-based care at speeds previously unimagined. Wearable medical tech allows physicians to monitor patients from afar, and telemedicine has emerged as an economical means by which to provide care to all corners of the world. It is against this backdrop that we consider the integration of technology into the residency application process. This article aims to assess the implementation of technology in the form of web-based interviewing as a viable means by which to reduce the costs and productivity losses associated with traditional in-person interview days.