Jackson was born on September 18, 1995, in Belleville, Illinois. During his freshman year in high school, he attended Belleville East High School. He moved to California prior to his sophomore year in high school. Jackson attended Junípero Serra High School in Gardena, California. He played numerous positions including wide receiver, running back, defensive back, and return specialist. Jackson was rated by Rivals.com as a five-star recruit and was ranked as the number one athlete and sixth best player overall in his class. He committed to the University of Southern California (USC) to play college football. Jackson also played basketball and ran track and field in high school.

Jackson majored in communications with a real estate minor at USC. Jackson played in 12 games as a true freshman in 2014. He played cornerback, wide receiver, and return specialist. He was the Pac-12 Freshman of the Year. In the 2014 Holiday Bowl, he had a 98-yard kickoff return touchdown and a 71-yard touchdown reception in USC’s 45–42 win. He finished his freshman season with 50 tackles, three receiving touchdowns, and two return touchdowns.

In the 2015 season, Jackson finished with 27 receptions for 414 receiving yards and two receiving touchdowns. In addition, he recorded two punt return touchdowns and one interception return for a touchdown.

On November 12, 2016, Jackson intercepted two passes from Washington’s quarterback Jake Browning, helping the Trojans win their fifth straight game and upset the fourth-ranked Huskies, who were undefeated at the time.

On December 8, 2016, Jackson was awarded the 2016 Jim Thorpe Award as the nation’s top defensive back.

On January 16, 2017, Jackson announced he would forego his senior season and enter the 2017 NFL Draft.

NFL draft experts and analysts projected Jackson to be selected in the first or second round. Jackson received an invitation to the NFL combine and performed nearly every drill, except for the bench press, short shuttle, and three-cone drill. On March 22, 2017, he opted to participate at USC’s Pro Day along with JuJu Smith-Schuster, Zach Banner, Justin Davis, Taylor McNamara, Stevie Tu’ikolovatu, Chad Wheeler, Leon McQuay III, Damien Mama, and six other prospects. He ran positional drills and completed the three-cone drill, while also meeting with team representatives and scouts from all 32 NFL teams. Jackson was ranked the tenth best cornerback in the draft by Sports Illustrated, ranked the seventh best cornerback by ESPN, ranked the sixth best by NFLDraftScout.com, was ranked the fifth best cornerback by NFL analyst Mike Mayock, and was ranked the second best cornerback by NFL analyst Bucky Brooks.

On May 23, 2017, the Titans signed Jackson to a fully guaranteed four-year, $11.28 million contract that also includes a signing bonus of $6.34 million. He competed with Logan Ryan, LeShaun Sims, Brice McCain, and Kalan Reed throughout training camp for the vacant starting cornerback positions after the departure of Jason McCourty and Perrish Cox during the off season. Head coach Mike Mularkey named him the starting cornerback, opposite Logan Ryan, and punt returner to begin the regular season.

On May 1, 2020, the Titans exercised the fifth-year option on Jackson’s contract. He was placed on injured reserve on September 14, 2020 with a knee injury. He was activated on November 11, 2020.