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Harry Keiley began his career as a high school government and economics teacher. He has served as president of Santa Monica-Malibu Classroom Teachers Association and chair of the California Teachers Association Political Action Committee.

He was appointed by the Santa Monica City Council and served a term on the Santa Monica Recreation and Parks Commission. He was an original member of the Los Angeles Alliance of New Economy (LAANE) board and is currently a member of the board at Step Up on Second; a non-profit committed to housing chronically homeless individuals, including U.S. veterans.