While still in his teens, Cressman applied himself to his first entertainment related jobs, it was a position as a weekend morning host on the local radio station, which he took on at the age of 16. “I had no experience, but I thought it would be fun, so I gave it a whirl.” The impetuous decision laid the groundwork for Cressman to later enrol at Mount Royal College for the broadcast journalism program. Following a year of college, Cressman worked for CMT, CKRY, and CJAY in Calgary, in “on air” capacities. In the fall of 1999, Cressman accepted a position as an agent with a Calgary based booking agency. “Once again, I had no experience and clue what I was doing, but working for straight commission stimulates your sink or swim instinct.”
Six years and change later, Cressman partnered with world renowned concert promoter Ron Sakamoto to buyout his former employer and create and establish the award winning Cressman Sakamoto Agency Inc. The boutique agency quickly defined itself in the marketplace by providing impeccable service to clients and customers. Representing elite Canadian Country music stars like Johnny Reid, George Canyon, Terri Clark, and other world class artists, CSA Inc has also earned a reputation as one of Canada’s most reputable entertainment procurement agencies.