Olivia Orlando-Donovan

Olivia Orlando-Donovan advises and defends employers in New York and Connecticut on workplace law, focusing on discrimination, harassment, retaliation, whistleblower, and wrongful termination matters. She provides day-to-day counseling on compliance, performance management, and workplace investigations. Olivia represents companies in state and federal courts, as well as before various human rights commissions and labor departments. She also handles mediations and arbitration proceedings involving employment and labor disputes.

In addition to her litigation and counseling work, Olivia delivers in-person and virtual training for in-house counsel, HR professionals, managers, and executives on workplace investigations, leave administration, and performance management. Her sessions are known for being interactive and engaging by blending real-world scenarios and related pop culture references to make complex employment laws accessible, memorable, and practical for business leaders.

Before joining Ogletree Deakins, Olivia practiced at another AmLaw100 firm, litigating employment disputes in New York state and federal courts, as well as administrative agencies. She previously served as an Assistant District Attorney in the Bronx County District Attorney’s Office, where she prosecuted hundreds of violent felony cases. As a member of the Trial Bureau, she tried numerous jury and bench trials to verdict, presented cases to the grand jury, examined expert, law enforcement, and civilian witnesses, coordinated multi-agency investigations, and routinely negotiated plea bargains. This experience gives her a uniquely strategic perspective in employment litigation, alternative dispute resolution, and client counseling alike.

Olivia also served as an Assistant Corporation Counsel at the New York City Law Department, handling oral arguments, depositions, and defending City employees in personal injury and property cases. She drafted and argued motions, represented the City in hearings and conferences, and resolved cases through dismissals and settlements.

She earned her J.D. from Albany Law School, where she was executive president of the Student Bar Association and was published in the Albany Government Law Review. Olivia received her undergraduate degree from Northeastern University, where she was a member of the women’s rugby team and the Student Conduct Board. She remains actively involved with both institutions through their alumni mentorship and mock trial programs.