Masters was a pro scout for the Canadiens from 2013 to 2019, but before doing that, he was a member of several other NHL teams as their video coach. The St. Louis Blues, Florida Panthers and Colorado Avalanche all benefited from his services between 2001 and 2013.
Famous NHL GM Doug Armstrong was one of Masters' biggest mentors as he entered the field of hockey. Masters claims that Armstrong really believed and pushed pro scouts to go further, which helped him land and succeed at his job.