Sydney Montgomery, ESQ

I have over a decade of experience working with and inspiring students from all walks of life.

Growing up in a military and Jamaican household, education was extremely important. However, as a first-generation student, I also know firsthand how daunting the admissions process can be. I owe the success of my college and law school admissions process to my dedicated teachers and parents who pushed me to achieve my full potential. Through S. Montgomery Admissions Consulting, I am blessed to do the same for other students. To learn more about how I started consulting, you can read my full story here.

As the first lawyer in my family, and as a graduate of Princeton and Harvard Law School, I have used my platform since 2012 to help students break down generational barriers and step confidently into their future. Issues of diversity, equity, and inclusion are incredibly important to me. I am a Co-Founder of College Equity First, Inc. a Maryland 501(c)(3) non-profit with a mission to motivate colleges and universities to become places where women and BIPOC students are as safe, valued, supported, developed, and celebrated as other students. In 2021, through data collection, analysis, and substantive interviews, College Equity First, Inc. synthesized quantitative and qualitative data about each institution into the College Equity Index™. Using an alphanumerical rating system, the College Equity Index™ ranked 105 top private colleges on 19 different criteria as they related to the Black experience on campus.

Additionally, I sit on the Board of the Institute for Anti-Racist Education, a New Jersey 501(c)(3) non-profit dedicated to creating decolonizing pedagogy and anti-racist curriculum. Outside of these formal roles, I volunteer my time with Law School Transparency (LST), a 501(c)(3) non-profit with a mission to increase transparency and consumer information regarding the law school application process. I work with the Executive Director, Kyle McEntee, to create training modules for college and university prelaw advisors as well as independent educational consultants.

I received my Bachelor of Arts in English and a Certificate in French Language and Culture from Princeton University, and my Juris Doctor from Harvard Law School. I completed the Independent Educational Consultant Certificate from UC Irvine, Division of Continuing Education.

I am a member of the National Association for College Admission Counseling, the Potomac and Chesapeake Association for College Admission Counseling (PCACAC), and I currently sit on the Graduate Committee and the Ethics Committee of the Independent Educational Consultants Association (IECA). In 2020, IECA named me one of seven inaugural recipients of the “Making a Difference Award” for positively contributing to the profession and membership. In 2021, PCACAC named me a Counselor of the Year.

My virtual consulting model allows me to serve students throughout the United States and abroad. My students live in New York, New England, Washington, D.C., Maryland, Virginia, Colorado, Georgia, Florida, California, Canada, Turkey, and Japan, among other places.


2021 Counselor of the Year

Potomac and Chesapeake Association for College Admission Counseling

2020 “Making a Difference Award” Recipient

Independent Educational Consultants Association