Meet Sydney

As a two-time six-figure entrepreneur, Sydney coaches women of color and first-generation professionals on entrepreneurship, thought leadership, and post-graduate success.

Sydney has spoken on national and international stages as a keynote speaker, conference panelist, commencement speaker, workshop leader, and more.

Sydney cares deeply about making an impact and giving back to the community and sits on the boards of several non-profit organizations. Sydney is 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™ that ranks 105 top private colleges on the campus climate for Black students.

Sydney Montgomery (Forbes 30 Under 30) is the daughter of a Jamaican immigrant mother and military parents. She was the first person from her high school to go to Princeton University and then later Harvard Law School. She has dedicated her life and career to supporting first-generation students in higher education and first-generation professionals in business. Sydney is a professional writer and speaker and her TEDx talk, Breaking Barriers, Building Futures: The Power of First-Generation Minds to Shape Business Success centers on tangible ways to support first-generation students and professionals.

Sydney is the Executive Director and Founder of Barrier Breakers®, a nonprofit that has worked with 7,000 first-generation and other marginalized students on the college and law school application process. She holds a B.A. in English from Princeton University, a J.D. from Harvard Law School, a Certificate in Independent Educational Consulting from UC Irvine, and a Certificate in Anti-Racism in Urban Education from UNC Charlotte. Sydney is a member of the Forbes Nonprofit Council and has been featured in Inc., Forbes, FastCompany, Medium, CNBC, and others.

Sydney sits on the Board of Advisors to Girls with Impact, the only live, online entrepreneurship program made just for girls.

Sydney is a member of the National Association for College Admission Counseling, the Potomac and Chesapeake Association for College Admission Counseling, and currently serves as a Graduate Committee member and Nominating Committee member of the Independent Educational Consultants Association (IECA).

Honors and Awards.

  • 2024 Forbes 30 Under 30 (Social Impact)

    Named one of 30 of the brightest young entrepreneurs, leaders, and stars in the country in the Social Impact Category.

    https://www.forbes.com/30-under-30/2024/social-impact?profile=sydney-montgomery

  • 2021 Kappa Alpha Theta 35 Under 35

    Recognizes young alumnae ages 35 and under for their outstanding accomplishments after college. The award has many categories to recognize all the areas where Thetas excel.

    https://www.kappaalphatheta.org/members/recognition/35-under-35

  • 2021 UCI Alumni Achievement Award

    Given to individuals who have demonstrated how the education and skills gained from the University of California, Irvine, DCE certificate program were applied in a distinctive and notable way.

  • 2021 PCACAC Counselor of the Year

    Recognizes Potomac and Chesapeake Association for College Admission Counseling members who go above and beyond in their work with students. Selection criteria include expertise, impact, advocacy, commitment to equity, and innovation in the industry.

    https://www.pcacac.org/counselor-of-the-year-award

  • 2020 IECA Making a Difference Award

    For positively contributing to the Independent Educational Consultants Association and profession, pushing for cultural competency training, and leading anti-racism efforts through presentations and articles.

    https://floridanewstimes.com/maryland-consultant-sydney-montgomery-wins-iecas-first-making-a-difference-award/91943/

  • 2018 Clarksburg High School Commencement Speaker

    Chosen by the Class of 2018 Class Officers to lead and inspire students at commencement to an audience of 4000+ individuals, including families, students, and educators.

  • 2010 American Baptist Churches of the South Oratorical Contest Winner

    ABCOTS is a non-profit corporation associated as a covenanting Regional organization with the American Baptist Churches, U.S.A

What People Are Saying

 

“You’ve given laughs and light to a very stressful and nerve-wracking time. I greatly appreciate your spirit and guidance.”

— Sofia F.

 

“Your feedback and input have been really valuable and the applications that I'm sending out are stronger because of your help.”

— Chad S.

“After hearing your experiences and advice, law school seems less like a pipe dream and more like a realistic goal.”

— Daniel H.

 

“Sydney believes in your abilities and is truly excited to cheer you on in the process which is invaluable.”

— Peyton T.