Santhosh started off his career with Re/Max in 2004, where he achieved success in a short span as sales representative. By 2009, he had become The Top individual person at Re/Max. His aggressive style of marketing which involved billboards, bus shelters, and print media, established him as a big brand in Mississauga and the areas around. In 2010, Santhosh started Santhosh Mathew Team it became The Top Team with Re/Max office with diamond club 2011 through 2013, and was awarded a Life Time achievement award for 2012. With Santhosh at the helm the team was among the top 1% Teams in GTA during this time.