After guiding his side to promotion via the play-offs, he was sacked from his position in the club in January 2024 with Harriers then bottom of the table, 7 points from safety.

Born in Dudley, West Midlands[4] into a sporting family (his father was a footballer with Halesowen Town and his younger brother Mike became a rugby union professional),[5][6] Penn began his career at Birmingham City in their youth system in July 2001.

[citation needed] Penn signed for Cheltenham's League Two rivals York City on 6 January 2014 on a two-and-a-half-year contract for an undisclosed fee.

[12] On 22 September 2016, Penn joined National League club Gateshead on a one-month loan until 25 October, having only made two appearances for Carlisle.

[23] Penn won the award again for January 2022 after winning more points than anyone else across the course of the month as well as defeating Championship side Reading in the FA Cup third round.

Penn bolstered his squad mid season, signing the likes of Christian Dibble, Kyle Morison and Joe Leesley.

Harriers form improved greatly, Penn's side then won their last 6 league games, including beating Kettering Town 3-0 on the final day of the season, finishing in the play off positions as a result.