Raymond began his journalism career in 2000 in Collingwood before moving on to Midland in 2004 and then to Barrie in 2005 to work on the regional desk. In 2006, he went back out as a general assignment and crime reporter-photographer. He was also city editor and multimedia editor at Barrie's former daily newspaper from 2011 until 2017, upon its closure. Along the way, Raymond has garnered provincial awards for investigative reporting in addition to spot news, agriculture, business, entertainment and sports. He was nominated for a National Newspaper Award as part of a team for their reporting on the Five Points fire in Barrie in 2007.