My passion, legal skill, and commitment to justice stem from years of work in both the private and non-profit sectors. After graduating from Harvard Law School in 2007, I worked for five years in Washington, D.C. at the nationally recognized law firm Covington and Burling. During that time, I practiced tax law and conducted internal investigations of large publicly-traded corporations, while at the same time taking on significant pro bono cases ranging from representing indigent defendants in landlord-tenant court to filing a clemency petition on behalf of a mentally disabled person on death row in Virginia. In 2008 at the height of the financial crisis (between my time at Covington), I also clerked for Judge Elizabeth S. Stong at the U.S. Bankruptcy Court in the Eastern District in New York in Brooklyn.

Starting in 2013, I worked for over three years at a premier Hawaiʻi law firm doing litigation, appeals, internal investigations, real estate, and multi-million transactional work. In September 2016, I became Legal Director at the American Civil Liberties Union of Hawaiʻi, where I managed their impact litigation docket on a wide range of civil rights and liberties issues, including free speech, disability rights, privacy and technology, due process, and equal protection. At the ACLU, I defended and advanced the civil rights and liberties of everyone in Hawaiʻi, but particularly of those most marginalized by the legal system and society, including before the Ninth Circuit Court of Appeals and the Hawaiʻi Supreme Court. I am also a lecturer on civil rights and liberties at the University of Hawaiʻi at Mānoa at the William S. Richardson School of Law.

After four and a half years at the ACLU, I launched Caballero Law to marry my expertise on civil rights and liberties with my passion for justice and for helping others through complex legal problems. My practice now primarily focuses on appellate litigation, civil rights and liberties cases, assisting working professionals with difficult employment and licensing situations, and acting as outside general counsel for various non-profits and small businesses.