[3] Following one season with the Hoosiers, Penn returned to Indy Eleven, signing a professional contract with the club on August 25, 2020.
[4] Penn was eligible for the 2021 MLS SuperDraft and was selected 10th overall by Inter Miami CF on January 21, 2021.
[6] On July 30, 2021, Penn joined USL Championship side Charleston Battery on loan for the remainder of the 2021 season.
[8] On March 8, 2022, Penn signed with Chicago Fire II ahead of their upcoming inaugural season in the MLS Next Pro.
[9] On March 3, 2023, it was announced that Penn had signed with MLS Next Pro side Portland Timbers 2 for their 2023 season.