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 daughter of military and immigrant parents and as a lower-income college student, Sydney battled insecurities, financial challenges, and debilitating chronic illnesses to defy societal labels and expectations. Now, as a TEDx Speaker and Forbes 30 under 30 entrepreneur Sydney inspires others to believe in themselves, find their voice, and confidently pursue their goals no matter their background or obstacles. Sydney holds a B.A. in English from Princeton University, a J.D. from Harvard Law School, a Masters of Theological Studies from Princeton Theological Seminary, 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, US News, Medium, CNBC and others.

Her TEDx talk, “First-Generation Graduates Drive Business Success,” has over 137,000 views.

Board of Directors

  • Dr. Michele Evard

    Secretary

    Michele Evard, Ph.D. is the founder of Evard Educational Consulting, where she helps students with homeschooling, high school, and college planning. She holds a Ph.D. from MIT, an M.S. in Computer Science from the University of Oregon, and a B.S. in Mathematics and B.A. in Computer Science from Andrews University.

  • Ibrahim Firat

    Treasurer

    Ibrahim Firat brings over two decades of experience at the intersection of nonprofit leadership, business strategy, and financial stewardship with deep expertise in nonprofit finance and strategic growth.

    Ibrahim is the Chief Educational Consultant and Co-Founder of Firat Education, a nationally recognized firm providing test preparation and college consulting services. He has previously served as President and Treasurer of the Independent Educational Consultants Association (IECA), where he guided the organization through major governance and financial transitions. He is also the former Vice President of the iWrite Literacy Organization, where he helped scale programs that empower young writers. In addition to his education-focused work, Ibrahim is the Co-Founder and strategic lead at Nexus Futbol Academy, a unique private soccer school that merges academics and athletics, breaking barriers for talented youth athletes seeking holistic development.

    Ibrahim holds an MBA and a BA in History from the University of St. Thomas (TX), as well as a Certificate in Entrepreneurship from Babson College.

  • Dean Tracy Simmons, Esq

    Tracy L Simmons is the Associate Dean of Admissions and Student Affairs at Howard University School of Law. Prior to joining Howard Law, she worked for the University of San Diego School of Law as the Assistant Dean of Admissions, Financial Aid and Diversity Initiatives and she also worked for the University of the Pacific, McGeorge School of Law, as the Senior Assistant Dean for Admissions, Diversity Initiatives and Financial Aid. Most recently, Simmons is a co-founder of the Womxn of Color Collective for law schools professionals, co-chair of the Legal Professions Chapter of the National Association of Diversity Professional in Higher Education (NADOHE), and has joined USD Law’s Children’s Advocacy Institute Council for Children (CAI). Simmons has a BA in Psychology with a minor in African American Studies and MA Education with an emphasis Multicultural Counseling from San Diego State University and earned her J.D. from Golden Gate University School of Law.

  • Yolanda Ingram, Esq.

    Yolanda Ingram is the Director of Access to Law School of Education Programs at the University of Pennsylvania Carey School of Law. After completing her B.A. in English, Yolanda attended Washburn University School of Law as a first-generation law student. She began her career at a mid-sized law firm and eventually became a professor at Temple University. Her journey led her to her current role supporting underrepresented students in applying to law school.

  • Robin Ladd, Esq.

    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.

  • Brandon Rhodes

    Brandon Rhodes an experienced strategy and analytics professional with a track record of leading cross-functional strategic initiatives. He holds a B.S. in Operations Research and Financial Engineering from Princeton University and has 8+ years of experience as an analyst. He is currently the Manager of Consumer Growth, Strategy, & GTM at Affirm.

  • Dr. Richard Thornton

    Richard Thornton is an engineer by degree and a scientist in practice looking to find novel intersections between collective cell behaviors and bioprocess engineering. He is currently a Molecular Biology Ph.D. Candidate at Princeton University and holds his B.S. in Biological Systems Engineering from North Carolina A&T University.

  • Dr. Samantha Andrews

    With over two decades of experience in clinical research and higher education, Sam is responsible for the development of clinical evidence strategies to secure market access and global expansion of medical devices with Smith+Nephew. Prior to pursuing a career in the medical device industry, she led the first Orthopedic Research and Innovation group in Hawaii, providing research opportunities to current and aspiring medical students and residents. Sam holds a PhD in Kinesiology and Rehabilitation Science from the University of Hawaii and a MS in Athletic Training from the University of Kentucky.

Board of Advisors

  • Ayana Dow, Esq.

    Ayana Dow is an associate at WilmerHale where she 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.

  • Michael Hogan

    Michael F. Hogan is an executive with over 40 years in the financial services industry. He is currently an adjunct professor at Bryant University and a course facilitator at Cornell University. He holds a Juris Doctor from Suffolk University Law School; Master of Art History from Lindenwood University; and a Bachelor of Arts in French Language and Literature from Bates College. He is currently a PhD candidate at the Institute for Doctoral Studies in the Visual Arts where his scholarship concentrates on the aesthetics of displacement in street art in context of twentieth and twenty-first century continental philosophical thinking. Michael splits his time in Truro, MA, Boston, MA and Miami, FL

  • David Sullivan, Esq.

    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.

  • Karen Ali, Esq.

    Karen Ali serves on the boards of The Auxiliary to the Isabella McCosh Infirmary (Princeton University), the Association of Black Princeton Alumni (ABPA) and Our Kids Read. 

    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.

  • R. Tamsin Jones

    R. Tamsin Jones is the Managing Director of The Channing Company, specializing in organizational transformation and growth. With expertise in change strategies, leadership development, and crisis management, she helps businesses and individuals navigate change, improve performance, and build resilience. Tamsin brings executive experience in strategy, operations, and HR, allowing her to align people, processes, and strategy for sustainable growth. A systems thinker with a background in process improvement, she has led large-scale change management initiatives, executive coaching programs, and organizational development efforts across industries. In addition to her consulting work, Tamsin is the Founder and Executive Coach at Coach Tamsin, where she focuses on performance, leadership, and executive coaching for women.

    She is currently pursuing a doctorate in Organizational Change and Leadership at the University of Southern California’s Rossier School of Education, building on her two Master’s degrees: an M.S. in Human Resources Management and Development from New York University and an M.A. in Human Services from Lincoln University of Pennsylvania. Tamsin is a proud first-generation college graduate.

  • Wesley C. Dias, Esq.

    Wesley C. Dias, Esq. was cofounder and CEO/President of the Argosy Consulting Group, (ACG) incorporated, 1988. In 2009, ACG was restructured into Argosy Consulting Group, LLC (ACG) with Mr. Dias as CEO/President. ACG is a multi-disciplinary consulting firm providing expert technical services and program support to public and private organizations in the areas of information technologies and management services.

    Mr. Dias has more than 47 years of public administration, business, and legal experience which include 33 years of Federal service. He has acquired extensive managerial and communication skills while gaining substantive operational expertise in the areas of strategic planning, budget, personnel, security, policy and procurement.

    Mr. Dias earned a B.A. degree with honors from Syracuse University, a M.P.A. from Princeton University, and a J.D. degree from Columbia University. Among his awards and honors are Who’s Who Amongst Students in American Universities and Colleges, designated one of the Outstanding Young Men of America by the U.S. Jaycees and recipient of the Syracuse University Orange Circle Award for outstanding community service and philanthropy. Mr. Dias is currently a member of the Columbia Law School Association Board of Directors, the Syracuse University Maxwell School Dean’s Advisory Board and the Syracuse University Office of Multicultural Affairs Advisory Board.

  • Tamara Baptiste

    Tamara Baptiste is a dynamic college admissions coach, speaker, author, and engineer determined to increase the presence of women in science, technology, engineering, and math careers. She is adept at building bridges and partnerships, facilitating discussions meant to find common ground, and building high-performing, motivated teams and trust within the community. A trusted advisor, Tamara employs an award-winning, empathetic and transparent leadership style.

    Tamara mentors men and women whose goals include growing and applying their skills, navigating difficult situations, defining their goals, and devising a course of action to achieve them.This passion led her to launch The College Application Specialist™ a consulting firm providing families and students with the information needed to confidently apply to higher-education opportunities that fit them academically, socially, and financially. Tamara has partnered large county library systems and churches in Maryland, DC, and Virginia, the Anne Arundel County NAACP, and True Ground Housing (formerly APAH) to provide college admissions and financial aid knowledge to thousands of parents and teens. Since 2015, her students have gained admissions to over 65 prestigious colleges and universities (including the Ivy League and Top 20) with over $15MM in merit aid, scholarships, and high-profile scholarships such as the Jack Kent Cooke Scholarship and the USC Presidential Scholarship.

    Tamara graduated from Cornell University with a BS in Engineering and a M.Eng. in Engineering Management. She holds a College Counseling and Higher Education Certificate (with Distinction) from the UCLA, and an Executive Certificate in Organizational Development and Change Leadership Consulting from Georgetown University. Tamara is a member of the ITSMF, SACAC, PCACAC, and IECA. She is also a proud member of Top Ladies of Distinction – Concord Chapter and the Queen City Metropolitan Chapter of the National Coalition of 100 Black Women, Inc.

  • Roxanna Cruz

    Roxanna Cruz is an accomplished, results-driven enrollment professional with over 20 years of working in higher education. Her extensive experience in developing and implementing comprehensive plans to recruit and retain talented and diverse individuals has been proven through her track record of consistently meeting and exceeding university and law school enrollment goals. Roxanna’s commitment to diversity, equity, and inclusion through her leadership is evident in her ability to not only help shape a class that is reflective of the world, but also in recruiting, developing, mentoring, and leading high-functioning diverse teams.

    Roxanna recently re-entered law school admissions where she serves as the Associate Dean of Admissions at Ave Maria School as of January 2023. Prior to this role, Roxanna held the position of Associate Vice President of Enrollment at Barry University in Miami Shores where she oversaw all undergraduate, graduate & professional enrollment. Roxanna also served as the Assistant Dean of Admissions at Barry University School of Law, Associate Director of Recruitment & Marketing at FIU Law, and as Director of Student Recruitment at Miami Law.

    Roxanna holds a Bachelor of Arts in Organizational Leadership from St. Thomas University and a Master of Business Administration in Management at Nova Southeastern University. As a first-generation college graduate, Roxanna takes pride in her accomplishments and her professional development in enrollment management. Roxanna’s creativity, adaptability, innovative thinking, and passion for access to higher education has provided successful outcomes in many aspects of her work. In addition, she considers her most prominent role to date as that of wife and mother of four children.

  • Benita Blackwell

    Benita Blackwell is a proud first-generation college graduate and passionate advocate for educational equity, technology integration, and student transformation. Raised in an underserved South Georgia community, Benita’s early life was shaped by both hardship and hope. Though her parents served in the U.S. military, she was raised by a single mother who instilled in her the values of education, resilience, and purpose. She went on to graduate as the Salutatorian of her high school class and later charted her own path at Wesleyan College, where she helped create her interdisciplinary major and became one of the first three graduates with a degree in Computer Information Systems.

    With over 17 years of experience across K-12 education and Department of Defense-connected learning programs, Benita has served in roles including STEM Coordinator, Educational Leadership, Program Developer, and Equity-Focused Consultant. She is the founder of IMperfect Academy, a STEM microschool for underserved and overlooked students, and the founder of MindSpaced, an AI application and software agency. She is also the Co-Founder of Schooling, a digital platform using AI, gamification, and global access to reimagine student-centered learning.

    Known for designing inclusive ecosystems rooted in personalized learning, restorative justice, innovation, and real-world learning, Benita has helped thousands of students recover credits, accelerate academically, and reconnect with education. From launching school reintegration programs to developing global STEM curriculum her leadership continues to drive impact.

    Benita is committed to creating pathways for students who have been historically left behind—empowering them to reclaim their education, rewrite their narratives, and reimagine their futures. Her story—from first-gen student to tech-empowered education leader—fuels her mission to make sure the next generation knows: your beginning does not define your brilliance.