In late 2018, Whitehead co-founded indie development studio Evening Star, which launched its first game, Penny's Big Breakaway, in early 2024.
[6][7] In an interview with Steven O'Donnell of Good Game: Spawn Point, Whitehead proclaims that he spent "about a year or so" convincing Sega to let him work on the Sonic CD port.
[7] Although he, along with Headcannon, released a proof-of-concept video for a Sonic the Hedgehog 3 remaster in 2014, Sega did not greenlight the port, which Thomley assumed to be in part of Michael Jackson's contribution to the music.
Sonic Mania Plus was developed by Whitehead, Headcannon, PagodaWest Games, and the now included Hyperkinetic Studios.
[16] In late 2018, Whitehead and other development members behind Sonic Mania founded their own studio Evening Star,[17][18] where he serves as creative director and lead engine architect.
[18] In 2022, the studio signed a publishing deal with Private Division; their first title, Penny's Big Breakaway, was released in 2024.