Webb was born in Newport News, Virginia. He attended Warwick High School and Hampton Roads Academy under the tutelage of Coach Abe Mikell in Newport News, and played high school football for the Warwick Raiders. While working with Coach Abe Mikell, Webb developed his fundamentals and love of the game. He was a two-year starter at defensive back and wide receiver. Webb had seven career interceptions, two of which were returned for scores. He was named to first-team All-Peninsula District as a defensive back (2007), and earned honorable mention distinction as a junior.
He was also a standout track athlete at Warwick, he ran a career best time of 6.60 seconds in the 55 metres. He excelled in triple jump and long jump as well. He was named to the All-America Team in track and field.
Webb decided to enroll in the College of William & Mary, where he played for the William & Mary Tribe football team from 2008 to 2012. After redshirting in 2008, he was honored as the Colonial Athletic Association (CAA) Defensive Rookie of the Year. He was also selected to the All-CAA second-team as a cornerback and to the all-league third team as a punt returner. He was tied for second nationally with eight interceptions, including a pair of interceptions returned for touchdowns, and totaled 160 interception return yards.
In 2010, he was selected to the All-CAA first team as a cornerback and garnered second-team honors as a punt returner after finished the season with 42 tackles, 0.5 tackles for loss, an interception and six passes broken up. In 2011, he earned first-team all-conference honors at cornerback for the second consecutive season, and finished the season with 40 tackles, 3.0 tackles for a loss and two interceptions.
As a senior, he garnered first-team all-league distinction as a cornerback for the third consecutive season, he also earned second-team all-conference honors as a punt returner. He finished his career with nine postseason all-conference honors, and set a school record with 48 career starts. He started all 11 games and totaled 46 tackles, two fumble recoveries, a forced fumble, eight passes broken up and a tackle for loss. He was initiated as a member of Omega Psi Phi Fraternity at William and Mary.
Webb was selected by the Dallas Cowboys in the fourth round (114th overall) of the 2013 NFL Draft. Coming from a small college background, he looked overmatched in the appearances he made as a slot cornerback. He was eventually benched in favor of Sterling Moore, who was re-signed on November 25 after being released before the start of the season. He was inactive for the final game.
In the next year training camp, he was passed over by undrafted free agent Tyler Patmon and was waived on August 28, 2014.
Webb was claimed off waivers by the Pittsburgh Steelers on August 29, 2014. He was activated for 11 games and played mainly on special teams. He was released on September 5, 2015.
On September 9, 2015, he was signed to the Tennessee Titans practice squad. He was promoted to the active roster on November 8, for a game against the New Orleans Saints in which he recorded his first career interception. He appeared in 9 games (2 starts), while registering 22 tackles, one interception and three passes defensed. On September 2, 2016, he was released as part of final roster cuts.
On September 14, 2016, Webb was signed by the New Orleans Saints, to provide depth at the cornerback position after Delvin Breaux suffered a broken fibula. He played in 14 games with eight starts with the Saints, recording career-highs of 28 tackles and 11 passes defensed to go along with one interception.
On April 5, 2017, Webb signed a one-year contract with the Chicago Bears. He was released on September 2, 2017.