Sydney Montgomery, a distinguished Princeton and Harvard Law School graduate, has been recognized as a Forbes 30 Under 30 honoree for her remarkable contributions to education and equity. As the CEO and Founder of Outline It, a cutting-edge writing software designed for students with learning differences, and the Executive Director and Founder of Barrier Breakers, a 501(c)(3) nonprofit, Montgomery is dedicated to increasing access to higher education for BIPOC and marginalized students.
Montgomery’s commitment to breaking generational barriers began in 2012, leveraging her position as the first lawyer in her family to inspire and support thousands of students. Barrier Breakers has assisted over 7,000 students through the college and law school admissions process, helping to address the significant underrepresentation of Black and Hispanic law students, who constitute just 8% and 13% respectively, according to the American Bar Association.
A woman of profound faith, Montgomery is pursuing dual degrees in Christian Education and Formation and Masters of Divinity at Princeton Theological Seminary. Her academic achievements are complemented by a Certificate in Independent Educational Consulting from the University of California, Irvine, underscoring her dedication to educational excellence and support.
Montgomery’s impact extends beyond her nonprofit work. As a Co-Founder of College Equity First, Inc., she is driving efforts to transform college environments into inclusive and supportive spaces for women and BIPOC students. The organization’s College Equity Index evaluates and ranks top private colleges on their campus climate for Black students, providing crucial data to promote institutional accountability and progress.
Her influence in the field of education is further amplified by her roles on the boards of several nonprofits, including the Institute for Anti-Racist Education and Girls with Impact. These organizations focus on decolonizing pedagogy, anti-racist curriculum development, and empowering young female entrepreneurs through live, online programs.
Sydney Montgomery is an active member of key professional associations such as the National Association for College Admission Counseling and the Independent Educational Consultants Association, where she serves on the Ethics Committee. Her work in these associations highlights her commitment to ethical practices and professional standards in educational consulting.
Sydney Montgomery’s journey from the daughter of a Jamaican immigrant to a pioneering leader in education exemplifies her dedication to creating equitable opportunities for all students. Through her innovative initiatives and unwavering faith, she continues to inspire and uplift the next generation, ensuring that higher education becomes accessible and inclusive for everyone.
