After originally being assigned to the Houston Roughnecks, he announced he would not play for the league, but was traded to the San Antonio Brahmas midway through the season.

After redshirting his first year at East Carolina in 2013, Benkert appeared in three games in 2014, completing eight of 10 passes for 58 yards and an interception.

He was named East Carolina's starting quarterback heading into 2015, however he suffered a torn ACL before the season.

[15] On August 6, 2019, Benkert was placed on injured reserve after suffering a toe injury in the preseason.

[24] Benkert was elevated to the active roster on December 7, 2021, to replace Jordan Love, who had been placed on the reserve/COVID-19 list the day before.

[25] He saw the field for the first time in his professional career on December 12, kneeling the ball twice in the closing seconds of a 45–30 win over the Chicago Bears.

[33] On March 23, 2023, the Roughnecks traded Benkert's player rights to the San Antonio Brahmas following an injury to Reid Sinnett.

Benkert completed one of his six attempts for two yards and an interception in the team's 15–9 win over the Arlington Renegades.

[36] Late in the first half Benkert was hit following a throw and suffered three broken ribs,[37] but did not leave the game.

[42] Benkert's content mostly focuses on playing or teaching the popular video game series Madden NFL.