Holland has most notably served as the executive vice president and general manager of the Detroit Red Wings of the National Hockey League from 1997 to 2019, winning four Stanley Cup championships.

On July 18, 1997, he was promoted to general manager, executive vice president and alternate governor of the Detroit Red Wings.

[8] On April 19, 2019, the Red Wings announced that Holland had been promoted to senior vice president of the team, and signed a multi-year contract extension.

[13] Holland and his wife Cindi live in British Columbia and have four children: Brad, Julie, Rachel, and Greg.

[14] He is also an annual "SMWW Hockey Career Conference" speaker for the online sports-career training school Sports Management Worldwide, founded and run by Dr. Lynn Lashbrook.