Sydney Montgomery, Esq.

Executive Director & Founder of Barrier Breakers®

As the first lawyer in her family, the first person from her high school to
attend Princeton University, and a Harvard Law School graduate, Sydney Montgomery (Forbes 30 Under 30) has used her platform since 2012 to help students break down generational barriers and step confidently into their future. As the Executive Director and Founder of Barrier Breakers®, issues of diversity, equity, and inclusion are incredibly important to her.

Sydney 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 the University of North Carolina at Charlotte. She is a member of the Independent Educational Consultants Association and the Northeast Association of Pre-Law Advisors. Sydney is currently an MDiv/MACEF candidate at Princeton Theological Seminary. She speaks and leads workshops on issues of educational equity and diversity, equity, and inclusion in higher education, corporate, and faith-based settings. Sydney is a member of the Forbes Nonprofit Council and has been featured in Inc., Forbes, FastCompany, Medium, and CNBC, among others. Her TEDx talk, “Breaking Barriers, Building Futures: The Power of First-Generation Minds in Shaping Business Success” will be available online at the end of May 2024.

National Board of Advisors

  • Ayana Dow, Esq.

    Associate, WilmerHale

    Ayana Dow advises broker-dealers, financial institutions and other global and domestic financial entities on a broad range of regulatory and enforcement matters. Ms. Dow also regularly counsels companies on compliance issues relating to Commodity Futures Trading Commission, Securities and Exchange Commission, FINRA, and other self-regulatory organization rules and regulations

    Prior to joining WilmerHale, Ms. Dow was an associate in the financial services group at another international law firm in Washington DC. She was previously a policy fellow in the Office of Congressman James Clyburn.

  • David Sullivan, Esq.

    Partner, Ropes & Gray

    David is a partner in the asset management group. David focuses his practice on the representation of financial services firms, including open- and closed-end registered investment companies, private investment pools, registered investment advisers and broker-dealers. He represents a number of non-U.S. investment advisory firms.

  • Kaysia Early, Esq.

    Founding Attorney, Earley Law Firm

    Kaysia Earley is known for achieving exceptional results. As a Christian Attorney whose moral compass is grounded in faith and fellowship, she has gained a well-deserved reputation as a fierce litigator who zealously fights for her clients’ fundamental rights. Founding attorney for Earley Law Firm, PLLC, she focuses on both criminal and civil litigation and is a strong advocate for her clients. In 2022, she was honored as a member of The National Black Lawyers Top 40 Under 40.

  • Robin Ladd, Esq.

    Associate, Haynes and Boone

    Robin Ladd is an associate in the Finance Practice Group in the Dallas office of Haynes and Boone. Robin has represented both borrowers and lenders in a variety of transactions. Her practice focuses on subscription secured finance, acquisition financing and syndicated credit facilities.

  • Aja Flewelen

    Vice President, Diversity Talent Acquisition, TD Cowen

    Aja Flewelen leads diversity talent acquisition at TD Securities supporting campus and lateral recruitment. Aja is responsible for the firm-wide strategy, strategic partnerships framework, and colleague engagement model that enable TD Securities to attract, engage, and hire multicultural professionals.

    Prior to joining TD Securities, she led the Diversity Talent Acquisition Strategy and Sourcing team at American Express. In her most recent role, she served as Chief of Staff to the President of Enterprise Strategic Partnerships as a member of the Executive Committee Support Team.

    Ms. Flewelen brings over a decade of experience in the Human Capital and DEI space across the non-profit, public, and private sectors. Aja is also a proud and active member of Delta Sigma Theta Sorority, Incorporated. She earned a Bachelor of Arts in Sociology from Loyola Marymount University and a Master of Science in Urban Policy from CUNY Hunter College.

  • Karen Ali, Esq.

    Karen Ali is the president of the Board of Trustees of the New Jersey State Museum Foundation and serves on the boards of The Auxiliary to the Isabella McCosh Infirmary (Princeton University), the Association of Black Princeton Alumni (ABPA), the Latin American Legal Defense and Education Fund, Our Kids Read, and Passion of Hope International-US.

    Karen is also active in Princeton alumni activities. She is Co-Class Agent for the Class of 1978 and a member of Princeton’s Annual Giving Committee. In 2018, Karen received ABPA’s Alumni Service Award. In 2013, she volunteered through Princeton AlumniCorps’ ARC Innovators program for Good Grief, Inc. and edited an anthology of children’s essays, The Invisible Tattoo: True Stories about Children Grieving, Living, and Loving After Loss (2014). For more than 25 years, she has served as an administrator for the Fred Fox Class of 1939 Fund, a program that provides grants to students for academic-related projects.

    In December 2020, Karen retired from the New Jersey Hospital Association, where she served as senior vice president for community partnerships and prior to that role, general counsel.

    Karen received her A.B. in Sociology, magna cum laude from Princeton University and her JD from the University of Michigan Law School. She is a member of the New York and Virginia State bars and the United States District Court for the Eastern District of Virginia Federal Bar.