Transforming communities through knowledge, coaching and wealth-building strategies that last generations
Empowering Communities, Building Legacies
When Reggie’s Family Lost Their Chance at Homeownership in Brooklyn—We Knew Financial Education Must Be a Human Right
Reggie saw a home slip away. Yanni grew up hearing the familiar script—get a good job, work hard, retire—but never learned the wealth-building skills that turn survival into freedom. We started The LES Group to turn those gaps into tools—budgeting, investing, planning, and coaching—so more individuals and families keep the opportunities they earn.
Our why is personal. As a teenager in Brooklyn, Reggie watched his family lose a home because they lacked trusted financial guidance. Yanni grew up with a familiar gap: school and work never taught how to budget, invest, or plan for real financial wellness. One story shows what happens in a single missed moment; the other shows what happens over years of missing instruction. We built The LES Group to bridge both, pairing lived experience with leadership expertise to teach what we wish we’d learned sooner. The result: practical tools like budgeting, investing, planning, and coaching—that help families and organizations build wealth and keep it.
Our Journey
Founded in 2024, The LES Group was born to bridge generational gaps in leadership, education, and economic empowerment—with practical tools people can use right now. Co-founded by Reginald V. Bennett (Reggie)—a financial strategist shaped by Wall Street and lived experience—and Ayanna Hill-Gill (Yanni)—a nationally respected independent school leader—LES Group is minority- and women-owned, rooted in resilience, and committed to lasting impact.
Why Reggie
As a teenager in Brooklyn, Reggie’s family lost their chance at homeownership due to financial uncertainty and a lack of trusted guidance. That moment propelled a 30-year career helping individuals, families, and businesses to:
• build financial stability
• create generational wealth
• gain confidence through financial literacy
Why Yanni
In classrooms and boardrooms, Yanni leads independent schools with courage, clarity, and an eye toward inclusion. Over three decades, she:
• empowers educators and students
• builds leadership pipelines
• designs systems that advance equity and excellence
Our expertise spans education, analytics, coaching, and consulting. Our mission is singular: to create spaces where people and organizations, especially those underserved or underestimated, can learn, plan, invest, and leave a lasting legacy.
Meet The Leadership Team
Co-Founder and CEO of The Legacy Empowerment Solutions Group, LLC
Reginald V. Bennett, known as Reggie, is a visionary leader and highly skilled data analyst with over three decades of experience in analytics, financial modeling, and business intelligence. Currently serving as a Principal Data Analyst for Customer Success at Genesys, Reggie is renowned for his analytical prowess and exceptional ability to translate complex data into actionable insights.
With a robust educational background, Reggie holds an MBA from the University of Chicago Booth School of Business, a Graduate Certificate in Business Analytics from Georgia Institute of Technology, and a Bachelor of Arts in Economics from Dickinson College. His technical acumen is supported by certifications in Database Management from Columbia University and proficiency across a multitude of platforms including Teradata, Oracle, SAS, SQL, Tableau, and Snowflake.
Reggie’s career is marked by significant tenures at leading corporations such as Delta Air Lines, where he spearheaded agency sales development and analytics, and JPMorgan Chase,where he served as an Analytics Consultant. His innovative approaches at Delta contributed to generating approximately $500M in annual revenue, creating cost-saving strategies, and enhancing operational efficiencies through advanced data visualization tools.
Reginald V. Bennett, MBA - Senior Data Analyst, Customer Success & Strategic Business Leader
At Genesys, Reggie has been instrumental in developing statistical modeling and advanced data visualization for complex business needs. His strategic input is invaluable in steering company-wide projects, mentoring teams, and enhancing customer success initiatives through refined data analysis.
Beyond his corporate achievements, Reggie is actively involved in defining and advancing DEI initiatives, applying his expertise to foster inclusive environments and promote equity within the industry. He is a member of several professional associations, including the American Statistical Association and the Data Science Council of America, where he contributes to ongoing discussions on best practices and innovations in analytics. Reggie also engages in community service, volunteering his time and skills to local educational programs that aim to increase access to technology and analytics education for underrepresented youth.
Reggie also engages in community service, volunteering his time and skills to local educational programs that increase access to technology and analytics education for underrepresented youth. As a member of the Georgia Financial Educators Council & Advisory Board, he further extends this mission by championing financial literacy and promoting economic empowerment across the state
A compelling communicator, financial literacy educator, and strategic thinker, Reggie’s leadership extends to advising top management on financial and operational strategies, making him a pivotal member of any executive team. His profound understanding of market trends and his ability to foresee industry shifts make him an asset to the company Legacy Empowerment Group and its clients.
Co-Founder and COO of The Legacy Empowerment Solutions Group, LLC
Ayanna Hill-Gill, affectionately known as Yanni, is a trailblazer in the field of education and a fervent advocate for equity and excellence. With over three decades of experience in independent school leadership, Yanni has left an indelible mark on the institutions and communities she has served. She holds a Bachelor of Science in Biology and Chemistry from Dickinson College and an Ed.M. in Organizational Leadership from Teachers College, Columbia University.
Currently, as the President of ADVIS (Advancing Independent Schools), Yanni leverages her extensive background to enhance educational governance and leadership. Her previous roles include impactful tenures as Head of School at Atlanta Girls' School and Purnell School. At Atlanta Girls' School, she led the school through significant initiatives, including exceeding enrollment goals, building robust academic programs, and overseeing major renovations that modernized educational and communal spaces. Similarly, at Purnell School, Yanni’s leadership resulted in a notable increase in the school’s endowment and the successful execution of multiple facility renovations, enhancing the overall learning environment.
In addition to her leadership roles, Yanni is a co-founder and executive coach at Legacy Empowerment Solutions Group, where she employs a transformative coaching style to empower individuals to realize their potential and enact significant changes in their personal and professional lives. Her approach focuses on self-awareness, strategic goal setting, overcoming barriers, and fostering sustainable change.
Ayanna Hill-Gill, Ed.M., Executive Coach and Visionary Leader in Education
Yanni's influence stretches beyond local boundaries through her service on several boards, including the International Coalition of Girls’ Schools, The Association of Boarding Schools (TABS), and Emory University’s Visiting Board of Trustees. Her commitment to community service is varied, and she is actively involved in initiatives that support financial literacy, STEM, and leadership development for underserved communities.
Yanni’s professional journey is a testament to her unwavering dedication to fostering inclusive educational environments and developing the next generation of leaders. Her work continues to inspire and mold the educational landscape, ensuring that the principles of equity and excellence remain at the forefront of educational innovation and leadership.