Cheveldayoff was named General Manager of the Jets on June 8, 2011, eight days after the franchise relocated to Winnipeg from Atlanta, and has held the position ever since. The Jets have posted a winning record in five of his six seasons as General Manager, including winning 40 games last season (40-35-7) for the second time in three seasons.

Winnipeg has drafted and developed a strong crop of young players under Cheveldayoff's leadership, including 2016 second overall pick Patrik Laine, who scored 36 goals as a rookie last season and was a finalist for the Calder Trophy as the league's best rookie. Laine was joined by fellow first round picks Nikolaj Ehlers, Josh Morrissey and Nic Petan as players age 21-and-under that played on a regular basis for the Jets last season. Earlier this year, Winnipeg's prospect group was one of only two teams to receive an A+ rating by The Hockey News, which also selected the Jets as having the best group of prospects in the NHL.

In fact, 38.6 per cent of the 44 draft picks made by Cheveldayoff and the Jets between 2011 and 2016 have played in the NHL already, which is second-most in the league. Nine of those 44 draft picks (20.5 per cent) have played more than 70 games in that time which is second in the NHL, while three of those players have averaged 0.5 points per game in their career thus far, which leads the league.

The Jets were one of two teams in the NHL to have four players reach 60 points last season, including 2011 first round pick Mark Scheifele, who paced the Jets with 82 points. Five Jets players scored at least 20 goals and four of those players were age 23 or younger drafted by Cheveldayoff and his staff. As a team, the Jets had a share of the best record within the Central Division at 19-8-2 and went 2-1-1 against the Western Conference champion Nashville Predators.

Prior to his time in Winnipeg, Cheveldayoff spent two seasons with the Chicago Blackhawks serving in the role of Assistant General Manager/Senior Director, Hockey Operations. During Cheveldayoff's tenure, the Blackhawks won the 2010 Stanley Cup championship.

Before joining the Blackhawks in 2009, the Blaine Lake, Sask. native spent the previous 12 seasons as the General Manager of the American Hockey League's Chicago Wolves, guiding the franchise to four league championships, which included the 2002 and 2008 AHL Calder Cup championships and 1998 and 2000 IHL Turner Cup championships. Overall, Cheveldayoff has been a part of seven league championships during his management career, which includes two Turner Cups in three seasons as the Assistant Vice-President of Hockey Operations and Assistant Coach for the Denver and Utah Grizzlies.

Originally drafted by the New York Islanders with their first pick (16th overall) in the 1988 NHL Entry Draft, Cheveldayoff began his career in the AHL with the Capital District Islanders, serving as the alternate captain from 1991 to 1993. He held the same role with the Salt Lake Golden Eagles in 1993-94, earning the team's "Unsung Hero Award" after racking up a career-high 216 penalty minutes in 73 games.

Cheveldayoff spent four seasons with the Brandon Wheat Kings of the WHL where he played in 214 games and collected 81 points (12G, 69A), as well as 759 penalty minutes.