Before beginning her work as a legal assistant at Arnold & Porter Kaye Scholer LLP, Bailey began by managing various conferences and assisting with programming for American University's School of International Service (SIS), the Washington College of Law (WCL), and for the Professional Fellows Division of the U.S. Department of State. Following this work, Bailey transitioned into full time work as a legal assistant at Arnold & Porter Kaye Scholer LLP.
During her time at Arnold & Porter Kaye Scholer LLP, she has been a part of the Immigration and International Arbitration practice groups. Within the Immigration group, Bailey coordinates the firm's pro bono immigration cases and serves as a member of the Immigration Intake Committee. Bailey has also spent time both in the US and abroad acting on behalf of various firm clients. Predominately, she has worked to defend respondent states within various investor-state disputes.