In 1894 he was elected to the Kentucky General Assembly as a Democrat. With the support of the John Henry Whallen's Democratic machine, he defeated James F. Grinstead to be elected mayor of Louisville in 1909. Local newspapers ran stories intended to scare white voters into voting for Head, exploiting fears of the growing black community in Louisville.
Head oversaw efforts to reform the city's tenement housing, adding code to the city's charter forbidding various unacceptable practices by landlords. The city also began appropriating funding for the University of Louisville during his administration.
After his term as mayor, he served as a delegate to the Democratic National Committee and as president of the Louisville Water Company.
He is buried in Cave Hill Cemetery.