Naylor is a fifth-generation railway worker, and a prominent figure in the Winnipeg labour movement. She has been a union representative in the Canadian Brotherhood of Railway, Transport and General Workers, and has subsequently been active with the Canadian Auto Workers. Naylor was appointed to Manitoba's Workers Compensation Board in 1996, but resigned in April 2005 to protest what she described as the inappropriate treatment of former chair Wally Fox-Decent by the provincial government. As of 2007, she is the Canadian Auto Workers's national representative for Saskatchewan.