Sydney Montgomery

2025-2026 Obama Foundation USA Leader

Headshot of Sydney Montgomery, 2025-2026 Obama Foundation USA Leader

Founder & Executive Director, Barrier Breakers, Inc.

Gaithersburg, Maryland

Sydney Montgomery is the founder and executive director of Barrier Breakers, Inc., an organization dedicated to dismantling educational inequity by supporting first-generation, low-income, and historically marginalized students in accessing and succeeding in higher education and professional programs. Through her leadership, Barrier Breakers has provided over 7,000 students with professional development programs and events and strategic institutional partnerships, achieving a 100% college acceptance rate for high school students, with 95% earning merit scholarships. Drawing from her graduate scholarship in the intersection of faith and educational access at Princeton Theological Seminary, she has scaled her organization across 36 states to holistically support students by addressing their emotional, mental, financial, and academic needs.

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The Barack Obama Foundation is registered as a 501(c)(3) non-profit organization (EIN 46-4950751).

Meet the 2025-2026 United States Leaders

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Leaders

For emerging leaders who have demonstrated a commitment to advancing the common good.

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  • The Center
  • Building the Center
Future water terrace to honor Ann Dunham will feature Maya Lin sculpture
Join other Obama alumni in coming together to support the naming of the Water Terrace at the Obama Presidential Center in honor of the life and legacy of President Obama’s mother, Ann Dunham—as a gift for the President’s 61st birthday.
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  • Defending Democracy
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Copenhagen Democracy Summit
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  • Barack Obama
Watch: President Obama shares the vision of the presidential center
Watch President Obama share his vision for the Obama Presidential Center during a surprise visit with supporters and stakeholders—a vision for a public space that will honor history, help revitalize the South Side, and connect people throughout the communi
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