Chris Diamond began his ski industry career in 1972, when he joined Sherburne Corporation (which later became S-K-I Ltd.) at Killington Vermont, serving as assistant to the president. In 1977, he was appointed general manager of the company's Mount Snow Ski Resort and vice president of the Sherburne Corporation.

In 1994, he returned to Killington to serve as S-K-I Ltd.'s vice president of business development. In 1995, he was appointed vice president of Vermont operations for S-K-I Ltd., in which capacity he also served as president of the Killington and Mount Snow resorts. He returned to Mount Snow to serve as vice president and managing director in 1996, upon S-K-I Ltd.'s acquisition by American Skiing Company. In 1999, he moved to the Steamboat Ski & Resort Corporation where he currently serves as president of the resort as well as vice president for American Skiing Company.

Diamond is a past chairman of the National Ski Areas Association, and past board member of the Vermont Ski Areas Association. He currently serves as a chairman of the board of Colorado Ski Country USA. Diamond received a bachelor's degree from Middlebury College and a master's degree from University of Massachusetts.