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 Founder of S. Montgomery Admissions Consulting which specializes in working with first-gen 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/YouTube and launched the Barrier Breakers® scholarship fund in 2022. Sydney is a 2020 IECA Making a Difference Awardee, a 2021 Counselor of the Year (PCACAC), and a Kappa Alpha Theta 35 Under 35.