Ashley E. Obando

Ashley E. Obando is of counsel in the Washington, D.C. Region office of Jackson Lewis P.C. Ashley partners with clients to provide strategic advice on workplace law, helping them navigate challenges with solutions that align with their business goals. Drawing on her background in senior leadership roles, she approaches each matter with a practical, business-minded perspective, learning the client’s organization to deliver tailored guidance that mitigates risk and supports long-term success. 

Ashley brings more than a decade of experience in employment law and organizational leadership from her service in the federal government. Before joining Jackson Lewis, she held senior positions with the U.S. Agency for International Development’s Office of Inspector General (USAID OIG), including Chief of Staff and Acting Assistant Inspector General for Management, Communications, and Innovation. In these roles, she provided strategic counsel on human capital, DEIA, and organizational development initiatives, while also overseeing critical functions, including contracting and financial resources. 

Ashley’s broad perspective allows her to advise employers with both a legal and operational lens. She is experienced in guiding executives and HR leaders through high-stakes employment decisions, designing proactive strategies to minimize legal risk, and managing change in complex environments. Ashley represents employers in employment matters, including defending against claims of employment discrimination, wrongful termination, and wage and hour violations. Ashley also helps companies protect their business interests by enforcing non-compete agreements and addressing allegations involving trade secrets and confidential information. In addition to litigation, Ashley conducts internal investigations in response to employee complaints about workplace conditions, helping organizations of all sizes navigate sensitive issues with discretion and legal rigor. 

Ashley has particular experience working with government contractors and organizations in the international development and foreign aid sector. She understands the unique compliance, operational, and workforce issues faced by organizations that operate across borders and under heightened regulatory scrutiny, and she brings that insight to advising clients on employment law and workplace strategy. 

Earlier in her career, Ashley served as Senior Counsel in USAID OIG’s Office of General Counsel and as an Attorney Advisor at the U.S. Small Business Administration. In these capacities, she counseled leadership on employment decisions, labor relations, workplace investigations, and legal compliance, often navigating sensitive personnel and policy matters with significant organizational impact.