Tim Wilken started with the Toronto Blue Jays in 1977 as a Scout and was promoted to Scouting Director of the Toronto Blue Jays from 1996 to 2000 and the Vice President, Baseball Operations from 2001 to 2003. In 2004-05 he was a special assistant to the GM of the Tampa Bay Devil Rays. In 2006 he moved to the Chicago Cubs as the team's Director of Professional and Amateur Scouting, a position he held until 2012, when he became a Special Assistant for the Cubs.
In 2006 he received the Scout of the Year award, given only to scouts with 25 years of service.
Incomplete list of players he signed: Billy Koch, Jimmy Key, Vernon Wells, Orlando Hudson, Michael Young, Jay Gibbons, Craig Wilson, Casey Blake, Felipe Lopez, Alex Rios, Josh Phelps, Miguel Negron and Wade Townsend. While Wilken was national cross checker, he signed Shawn Green, Shannon Stewart, Roy Halladay, Steve Karsay, Chris Carpenter and Ryan Freel.