Cherokee began his career in the vacation industry in April 1999. He worked for Fairfield Resorts until December 2003. His next adventure was at Sunterra Resorts from April 2004 until July 2007. He finally moved over to Vacation Village Resorts from July 2007 until February 2008.

Over the years, he noticed a major service and caring void in the timeshare industry and decided to fill that void, and on February 17, 2008, CE Travelers Advantage Club (CETAC) was born. Business is booming by taking care of both timeshare owners and vacationers alike.

In 2021 Sharetime Consulting LLC was created to encapsulate all the offerings of Cherokee Edwards, from timeshares to motivational speaking.