Head made his professional debut with the Rookie-level Arizona League Padres, batting .283 with one home run and seven doubles over 32 games.[5] He did not play a minor league game in 2020 since the season was cancelled due to the COVID-19 pandemic.[6]
On January 19, 2021, Head was traded to the Pittsburgh Pirates as part of a three team trade that also sent David Bednar, Omar Cruz, Drake Fellows and Endy Rodríguez to the Pirates, Joe Musgrove to the Padres and Joey Lucchesi to the New York Mets.[7] He spent the 2021 season with the Bradenton Marauders of the Low-A Southeast, slashing .213/.362/.394 with 15 home runs, fifty RBI, and 16 doubles over 101 games.[8]
Head made 106 appearances for the High-A Greensboro Grasshoppers in 2022, slashing .234/.343/.387 with 10 home runs, 40 RBI, and 13 stolen bases.[9] He split the 2023 campaign between the rookie-level Florida Complex League Pirates and Greensboro, batting a combined .249/.318/.405 with five home runs, 23 RBI, and four stolen bases.[10]
Head returned to Greensboro for the 2024 season, playing in 102 games and hitting .208/.303/.383 with 13 home runs, 49 RBI, and nine stolen bases.[11] He began the 2025 season with the Double-A Altoona Curve, batting .116/.183/.174 with one home run, four RBI, and one stolen base. Head was released by the Pirates organization on July 26, 2025.[12]
On December 18, 2025, Head signed with the Kansas City Monarchs of the American Association of Professional Baseball.[13]