Gilbert began his career in coaching at the University at Albany. He worked l as a graduate assistant in 1987 and 1988 under Bob Ford.[6]
After Albany, Gilbert became the assistant offensive line and recruiting coordinator at the University of Pennsylvania for 1989 and 1990 under head coach Gary Steele.
In 1991, Barry Gallup and the Huskies hired Gilbert as their offensive line coach and recruiting coordinator. He remained with the team for three seasons.
After coaching at Northeastern, Gilbert was hired by Maine as the team's offensive line coach in 1994. After the 1995 season, he was given the additional title of offensive coordinator, in addition to his duties with the offensive line.
In 2000, Gilbert had his first opportunity as a head coach at Mansfield. He only remained with the team for one season.
In 2001, Gilbert returned to coaching the offensive line this time at Toledo under coach Tom Amstutz. Gilbert left the team after the 2003 season.
On February 6,2004 following his three-year run in Toledo,[7] went to UCF. There he went on to coach the offensive line also for three years.
In 2007, Gilbert returned to Toledo as the team's tight ends coach. However he only remained there for a single season.
Gilbert spent the 2008 season at the University of Houston, where he led an offensive line that helped the team rank second in the nation in passing and total offense and 10th in scoring offense.
In 2009, Gilbert was hired by Ron Zook as the Illini's offensive line coach.[8][9] In 2010, he added the title of assistant head coach.
He had a six-year stint with the Indianapolis Colts. First named an assistant offensive line coach in 2012,[4] he held the title of offensive line coach[10] from 2013[11] to 2015, and reverted to the assistant line coach in 2016[12] and 2017.
Gilbert coached the offensive line at the University of Arizona[13] in 2018,[14] while also having the title of run game coordinator.[15]
In 2019 Gilbert returned to the NFL becoming the Bucs offensive line coach.[5] Gilbert earned his first Super Bowl title when the Buccaneers won Super Bowl LV.[16]
In 2024, he followed Dave Canales to the Carolina Panthers and became the team’s offensive line coach.[17]