Berry played college football for Eastern Kentucky from 2009 to 2013.[5] In 2010, he was named to the All-OVC second-team and the OVC All-Newcomer team.[6] In 2011, Berry was named to the All-OVC first-team.[7] In 2013, he was named to the All-OVC second-team.[8]
Berry was signed by the Pittsburgh Steelers on April 14, 2015.[10] After a preseason in which he punted 19 times for an average of 49.8 yards per punt, the Steelers traded incumbent punter Brad Wing to the New York Giants.
On February 1, 2018, Berry, who was due to become a restricted free agent, signed a one-year contract extension with the Steelers.[11]
On March 13, 2019, Berry signed a two-year contract extension with the Steelers.[12]
On September 7, 2020, Berry was released by the Steelers after the team signed Dustin Colquitt.[13] He was re-signed on October 24, 2020.[14]
Berry signed another one-year contract with the Steelers on March 29, 2021.[15] He was released on August 26, after losing the starting job to rookie Pressley Harvin III.[16]
Minnesota Vikings
On September 2, 2021, Berry signed a one-year deal worth $990,000 with the Minnesota Vikings.[17] He re-signed with the team on March 16, 2022.[18] Berry was released by the Vikings on August 25.[19]
Pittsburgh Steelers (second stint)
On September 27, 2022, Berry was signed to the Steelers' practice squad. He was released on October 4.