Kiekhefer attended Oldham County High School in Buckner, Kentucky.

The Cleveland Indians selected him in the 37th round of the 2007 Major League Baseball draft.

[1] The St. Louis Cardinals selected Kiekhefer in the 36th round of the 2010 Major League Baseball draft and he signed After signing, Kiekhefer was assigned to the Johnson City Cardinals, and after one game, was promoted to the Quad Cities River Bandits where he finished the season with a 5.14 ERA in 28 innings pitched out of the bullpen.

[7] On February 17, 2018, Kiekhefer signed a minor league deal with the Cincinnati Reds.

In 6 appearances split between Las Vegas and the rookie–level Arizona League Athletics, he struggled to a 12.79 ERA with 6 strikeouts across 6+1⁄3 innings pitched.

He was hired by the Cardinals for the 2020 Season to be a minor league pitching coach for their State College (Low–A) affiliate.