Before being appointed to his most recent role in November 2005, Weiss served as president of the Walt Disney World Resort in Lake Buena Vista, Florida since 1994. He was named executive vice president of the Florida resort in 1996. Meg Crofton succeeded Weiss as president of Walt Disney World Resort in 2006.
Weiss began his Disney career as an 18-year-old Walt Disney World cast member in 1972. His first job was a "z-runner", a financial analyst who zeroed out cash registers at the end of shifts. He evidently was a ping pong champion in a cast member's tournament on year as well! In total he worked for the Disney company for 39 years when he retired in 2011.