Maile attended Covington Catholic High School in Park Hills, Kentucky, where he played for the school's baseball team. He set school records for batting average, on-base percentage, hits, walks, runs scored, runs batted in, doubles, and triples. He was named the Cincinnati Enquirer's Player of the Year in three of his four years at Covington Catholic, and was named Kentucky's Mr. Baseball in his senior year.
The Red Sox selected Maile in the 43rd round of the 2009 Major League Baseball draft, but he did not sign. Maile had asked the Red Sox for more money than they wanted to offer. He then enrolled at the University of Kentucky, where he played college baseball for the Kentucky Wildcats baseball team. In 2012, his junior year, Maile won the Southeastern Conference (SEC) Player of the Week Award twice, was an All-SEC Second Team member, and was a semifinalist for the Golden Spikes Award and the Dick Howser Trophy.
The Tampa Bay Rays selected Maile in the eighth round, with the 272nd overall selection, of the 2012 Major League Baseball draft. He was assigned to the Short Season-A Hudson Valley Renegades for the entire 2012 season, appearing in 61 games and batting .278 with three home runs and 41 RBI. In 2013, Maile played in 95 games for the Class-A Bowling Green Hot Rods. He finished the year with a .283 batting average, four home runs, and 49 RBI. During the offseason, Maile played for the Salt River Rafters of the Arizona Fall League.
In 2014, Maile played for the Montgomery Biscuits of the Double-A Southern League. The Rays promoted him to the Durham Bulls of the Triple-A International League at the end of August, but he did not appear in any games for the Bulls in 2014. In 97 games for Montgomery, Maile hit .268 with five home runs and 37 RBI. Maile played for the Bulls in 2015, hitting .207 in 89 games, and was promoted to the major leagues on September 1. He appeared in 15 games for the Rays in 2015, and hit .171 with two RBI.
Maile split time between Durham and Tampa Bay in 2016. He played in 58 games for the Bulls, hitting .242 with two home runs and 12 RBI. With the Rays, he appeared in 42 games and recorded a .227 batting average with three home runs and 15 RBI. The Rays designated Maile for assignment on April 2, 2017.
The Toronto Blue Jays claimed Maile off waivers on April 6. On April 28, Maile was recalled from the Triple-A Buffalo Bisons after Jarrod Saltalamacchia was designated for assignment. Maile was placed on the disabled list on July 4 with knee inflammation. An MRI later that day determined he had a torn meniscus. Maile was activated from the disabled list on September 1.
Maile was married on November 1, 2014 to Paige Maile, née Archinal.