He played college football for the Holy Cross Crusaders from 2012 to 2015 On May 3, 2016, the Denver Broncos signed Raymond as an undrafted free agent.

[6] In the season opener against the Buffalo Bills, Raymond was the kickoff and punt returner in his Jets debut.

[23] During Week 10 against the Kansas City Chiefs, Raymond caught a 52-yard reception from Ryan Tannehill and returned three kicks for 46 yards in a 35–32 victory.

On December 1, 2019, he scored his first NFL touchdown on a 40-yard pass from Tannehill in a 31–17 road victory over the Indianapolis Colts.

[24] On the 2019 season, Raymond totaled nine receptions for 170 receiving yards and one touchdown in eight games.

[25] In the divisional round of the playoffs against the Baltimore Ravens, he caught a 45-yard touchdown during the 28–12 road victory.

[26] In Week 3 of the 2020 season, Raymond had three receptions for 118 yards in the 31–30 victory over the Minnesota Vikings.

[32] On December 18, 2022, he ran 47 yards for his first career punt-return touchdown in a 20–17 win against his former team, the Jets.