Dailey worked his way up in the insurance industry
Dailey started as a claims adjuster for Mutual Service Insurance, joined Progressive Insurance and then formed auto insurance startup Reliant Insurance, which was sold to Bristol West Holdings in 2001. Dailey was COO of Bristol West, then president i n 2004 and took the company public with a $345 million valuation. He became CEO of Bristol West in 2006. It was acquired by Farmers in 2007, with Dailey named President of Farmers' Personal Lines. He was named CEO of Farmers on Jan. 1, 2012.