He played college football for the Oklahoma Sooners and originally signed with the Chicago Bears as an undrafted free agent in 2013.

Way joined the Commanders in 2014, making two Pro Bowls and earning second-team All-Pro honors in 2019.

[1] Way completed his bachelor's degree at Oklahoma in interdisciplinary studies in December 2012.

[4][1] The Chicago Bears signed Way as an undrafted free agent on April 28, 2013.

[6] He re-signed with the Bears for the 2014 offseason, but he was waived again after losing out to rookie Pat O'Donnell on August 18, 2014.

[17] In Week 10 of the 2018 season, Way punted five times for a net average of 47.8, downing four punts inside the 20-yard line, in a 16–3 win over the Tampa Bay Buccaneers, earning him National Football Conference (NFC) Special Teams Player of the Week.

[19] In Week 13 of the 2019 season, Way hit two of his five punts inside the 20 with an average of 58 yards per punt and a long of 79 yards in a 29–21 win over the Carolina Panthers, earning NFC Special Teams Player of the Week.

[20] For his performance in 2019, Way was voted to the 2020 Pro Bowl, as well as being named second-team All-Pro.

[26] In Week 11 of the 2020 season against the Cincinnati Bengals, Way punted five times with a gross average of 50.4 yards while landing three of them inside the 20 during the 20–9 win, later earning the NFC Special Teams Player of the Week award.

[30] Way was named NFC Special Teams Player of the Month for October 2022.

[34] He gave up his uniform number 5 in a deal with quarterback Jayden Daniels after the team selected the latter second overall in the 2024 NFL draft.