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Ayana Free


Professional Overview



Ayana Free is a senior legal advisor based in New York. She currently works as the Head of Litigation and Regulatory Compliance at Via, dedicated to powering public mobility by delivering efficient, advanced digital software solutions and turn-key transit operations to private and public partners globally.  

Ayana has over a dozen years of experience advising and providing counsel to scaling tech companies, governmental agencies, and Fortune 500 companies. She has established herself as a trusted leader and strategic partner who has consistently demonstrated the ability to mitigate risks and protect the company’s legal interests while also developing and implementing successful litigation strategies for complex commercial litigation and class actions. Having served in private practice, governmental and in-house legal roles, Ayana has developed a robust expertise in litigation management, internal investigations, labor and employment law, and intellectual property. She is passionate about leadership, diversity, equity and inclusion. Ayana practices mindfulness, values mentorship, and enthusiastically supports young women and professionals of color pursue their dreams.

Previously in her career, Ayana Free served as an Assistant U.S. Attorney for the U.S. Attorney’s Office for the Eastern District of Virginia in the Civil Division. Her role included drafting pleadings and motions, researching precedent, responding to discovery requests, and negotiating settlements, among other responsibilities. Prior to that role, she worked as an Associate with Cleary Gottlieb Steen & Hamilton in New York, where her primary focuses were Litigation & Arbitration as well as Enforcement & Regulatory Investigations. Ayana had the honor of serving as a Judicial Clerk for the late Hon. Reginald C. Lindsay and Hon. William G. Young in the U.S. District Court for the District of Massachusetts in Boston. 


Ayana graduated with honors from Spelman College in Atlanta, Georgia, with her B.A. in English. After graduating from Spelman, she attended New York University School of Law where she obtained her J.D. At NYU Law, Ayana received a Dean’s Scholarship, was a Junior Fellow for the Institute for International Law and served as Senior Note Editor for the Journal of International Law and Politics and Board Member of the Coalition for Legal Recruiting (CoLR).

Learn more about Ayana Free’s insights into business by checking out her blog page!

Past Positions



Senior Director of Legal Affairs
Sep 2019 – Aug 2020

Director of Legal Affairs
Sep 2017 – Aug 2019

Eastern District of Virginia

Assistant United States Attorney 
Jul 2013 – Aug 2017

Cleary Gottlieb Steen & Hamilton LLP

2009 – 2013

Organizations & Honors

  • Board Member, New York University Law School Alumni Association
  • “40 Under 40” Rising Star, New York University Law Alumni of Color Association 
  • Smithsonian National Museum of African American History and Culture, Ambassador


  • Commercial Litigation
  • Civil Litigation
  • Class Actions
  • Internal Investigations
  • Labor & Employment Law
  • Intellectual Property



Doctor of Law (J.D.)
New York University School of Law2004 – 2007
While attending New York University School of Law, Ayana Free was a member of multiple activities and societies including the Journal of International Law & Politics as Senior Note Editor, Institute for International Law & Justice as a Junior Fellow, Coalition for Legal Recruiting as a Board Member.

Bachelor of Arts (B.A.), English Language and Literature
Spelman College – 1996 – 2000
Ayana Free graduated cum laude from Spelman College with her B.A. in English Language and Literature. Studied abroad her junior year with Kalamazoo College Overseas Studies Program in Dakar, Senegal. While enrolled, she also received the Dean’s Scholarship.

Recent Blogs

The Importance of Juneteenth and Coalition Building

The Importance of Juneteenth and Coalition Building

Juneteenth is coming! On June 19, 1865, General Gordon Granger marched into Galveston, Texas. He announced that the 250,000 Black people still enslaved in Texas-- despite the Civil War’s end two months prior and the Emancipation Proclamation being two years old-- were...

Advantages of Female Leadership

Advantages of Female Leadership

Historically, male leadership has dominated the economy, with the vast majority of CEOs, board positions, and even lower levels of management being men.  With higher rates of female leaders at the upper echelons of leadership, though, in the business sector and...