Sydney Montgomery

2025-2026 Obama Foundation USA Leader

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

Founder & Executive Director, Barrier Breakers, Inc.

Upper Marlboro, 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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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
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Future water terrace to honor Ann Dunham will feature Maya Lin sculpture

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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

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