Caulfield will be serving as an assistant under head coach Ian Clerihew, who he played for during a standout career at Mars Hill College. Caulfield served as a captain for Mars Hill all four years, and was voted team MVP in 2008. Caulfield served a coaching internship at Mars Hill in early 2012 before moving on to coach the Massapequa (N.Y.) Soccer Club. He also has professional soccer experience, as he played for Livingston FC in Scotland for three years.