Benjamin was born in Rockford, Illinois. He had a successful amateur career while at the University of Memphis. In his freshman year of 2006, he finished tied third in the Conference USA golf championships. The following year he won his first collegiate tournament. In summer 2009, following his graduation, he won the U.S. Amateur Public Links, qualifying him for the following year's Masters Tournament. He finished 3rd in the 2010 Sunnehanna Amateur, 2nd in the Northeast Amateur, and he finished T-9 in the 2010 U.S. Amateur at Chambers Bay. He came through qualifying for the 2011 U.S. Open, and was one of three amateurs to make the cut.