Representative McKeown began her career in public service on the Coos Bay School Board, where she served for 11 years. In 2004, she was appointed by Gov. Ted Kulongoski to the Board of Commissioners of the Oregon International Port of Coos Bay, where she served for nine years and worked to acquire and rehabilitate the Coos Bay Rail Line. Rep. McKeown also served on the Energy Trust of Oregon board for 11 years and on the boards of various local non-profits.
Caddy was a member of the Oregon House of Representatives, representing the 9th district from 2013 to 2021. Prior to the role with the Port of Coos Bay, Caddy was the Program Supervisor for the ASPIRE program with Oregon Student Assistance Commission. During her time in office, Caddy served on many committees, including co-chair of Joint Committee on Transportation, Preservation and Modernization, Economic Development Committee, Agriculture & Natural Resources Committee, the Higher Education, Innovation, and Workforce Development Committee, the Task Force on Small Business, and the Pacific States Marine Fisheries Commission, and was chair of the Coastal Caucus. She was a member of the Legislative Commission on Indian Services.
Caddy currently works in Community Relations for NorthPoint Development and is principally involved with the development to establish a new container port in the area.