Sydney Montgomery

About Sydney Montgomery

Sydney Montgomery is the CEO of Outline It, Inc., an edtech software company that aims to close the equity gap in education through writing and the Founder of S. Montgomery Admissions Consulting which specializes in working with first-generation and minority college and law school applicants. The daughter of military parents and an immigrant mother, Sydney graduated from Princeton University and Harvard Law School to become the first lawyer in her family. Sydney hosts the weekly Break into Law School™ podcast and launched the Barrier Breakers® scholarship fund in 2022. Sydney is a 2021 PCACAC Counselor of the Year, a Kappa Alpha Theta 35 Under 35 Awardee, and was named one of Women's eNews 21 Leaders for the 21st Century.