In 1997, his amateur team, La Correta, played against the Carolina Dynamo of the A-League in a game where Hackworth shut down the Trinidad & Tobago international Stern John.
Following the 2007 U-17 World Cup, Hackworth joined Bob Bradley’s coaching staff as an assistant with the senior United States Men's National Team.
On November 9, 2009, Hackworth joined former U.S. Soccer colleague Piotr Nowak with the MLS expansion side Philadelphia Union as a coach and youth development coordinator.
In his first full season in charge of the Union, the squad ranked as high as second in the Eastern Conference the week of June 24 but failed to reach the playoffs by three points.
In December 2015, Hackworth was re-hired as U-17 National Team coach ahead of the 2017 FIFA U-17 World Cup in India and also oversaw the U.S. U-17 Residency Program.
At that tournament, he coached notable United States internationals Sergiño Dest, Josh Sargent, and Timothy Weah.
[7] As the head coach, he led the team to a USL Championship title in 2018, guided them back to the final in 2019 and in 2020 saw LouCity post the Eastern Conference's best regular-season record.
On April 27, 2021, it was announced that Hackworth and Louisville City had mutually terminated his contract and replaced by Danny Cruz.
[8] In October 2021, Hackworth was named director of coaching for Major League Soccer expansion club St. Louis City SC.
[9] On January 14, 2022, it was announced that Hackworth would serve as interim head coach for the club's MLS Next Pro side for the first half of the 2022 season.
While coaching at the University of South Florida, Hackworth was the chairman of the Conference USA's men's soccer committee.