Raymond began his journalism career in 2000 at the Collingwood Enterprise-Bulletin before moving on to the Midland Free Press in 2004 and then to the Barrie Examiner 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 the Barrie Examiner from 2011 until the daily newspaper's closure on Nov. 27, 2017. 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.