He was previously the general manager of the BC Lions (1993–94), Toronto Argonauts (1997, 1999), Ottawa Renegades (2002–04),[2] Saskatchewan Roughriders (2006–2010),[3][4] Edmonton Eskimos (2010–2012), and Hamilton Tiger-Cats (2016–2018).
[3] Tillman began his career as a football executive in 1981 as a member of the Houston Oilers' public relations department.
[5] From 1984 to 1993, Tillman served as executive director of the Senior Bowl, a game sponsored by National Football League designed to showcase top players graduating from United States colleges.
[7] The Lions success came in spite of regular fighting between head coach Dave Ritchie and owner Bill Comrie and a lack of team harmony.
[5] In 1995, Norton Herrick, a real estate developer from Orlando, Florida, announced plans to move the CFL's Las Vegas Posse to Tillman's hometown of Jackson, Mississippi.
[14] Part way through the 2006 CFL season, Tillman was hired as the Roughriders general manager after they fired long time GM Roy Shivers.
[2] He took over a team that had a tarnished reputation in the community after several players had run-ins with the law, including former linebacker Trevis Smith, who had been charged with two counts of aggravated sexual assault after he knowingly exposed two women to HIV without telling them.
[15] Tillman promised to clean up the team's image and the Roughriders adopted a code of conduct which required players to obey the law, act with honesty and integrity, respect others, and take responsibility for their actions.
[16] During Tillman's three years with the team they hosted three consecutive home playoff games and played in two Grey Cups.
[18] He also acquired many key players who would be part of the Roughriders 2013 championship season, including Darian Durant, Chris Getzlaf, and John Chick.
[6] In Tillman's first full season with the team, the Eskimos finished with an 11–7 record, which tied them with the Calgary Stampeders and BC Lions for first place in the West.
The move would be criticized as Jyles struggled at quarterback for the Eskimos while Ray led the Argonauts to victory in the 100th Grey Cup.
The team struggled offensively throughout the season and started three quarterbacks Jyles, Kerry Joseph, and Matt Nichols.