This article, from the “To the Point” series by the Undergraduate Medical Education Committee of the Association of Professors of Gynecology and Obstetrics, is a guide for advising medical students applying to Obstetrics and Gynecology residency programs. The residency application process is changing rapidly in response to an increasingly complex and competitive atmosphere, with a wider recognition of the stress, expense, and difficulty of matching into graduate training programs. The coronavirus disease 2019 pandemic and societal upheaval make this application cycle more challenging than ever before. Medical students need reliable, accurate, and honest advising from the faculty in their field of choice to apply successfully to residency. The authors outline a model for faculty career advisors, distinct from mentors or general academic advisors. The faculty career advisor has detailed knowledge about the field, an in-depth understanding of the application process, and what constitutes a strong application. The faculty career advisor provides accurate information regarding residency programs within the specialty, helping students to strategically apply to programs where the student is likely to match, decreasing anxiety, expense, and overapplication. Faculty career advisor teams advise students throughout the application process with periodic review of student portfolios and are available for support and advice throughout the process. The authors provide a guide for the faculty career advisor in Obstetrics and Gynecology, including faculty development and quality improvement.