He had the primary role in the North American production and localization of Square's role-playing video games released for the Super NES between 1991 and 1996.

Since then, his work in the video game industry shifted to a producer role at Big Rain, a company he co-founded, as well as others like Crave Entertainment and RealNetworks.

[8] He would fly to Japan for a typical project and have about thirty days to translate a script based on the finished Japanese version of the game, which had been broken up idiosyncratically by programmers to fit in cartridge memory.

English requires roughly twice as many characters as Japanese to convey the same meaning, which forced Woolsey to cut down the scripts to fit within the cartridge memory.

[9] Other titles he localized included Final Fantasy Mystic Quest, Secret of Mana, Capcom's Breath of Fire, and Chrono Trigger.

Woolsey's last project with Square was the translation of Super Mario RPG and left before the English localization of Final Fantasy VII began.

[10] In this role, he brought games such as Limbo, Dust: An Elysian Tail, Killer Instinct, and Ori and the Blind Forest to Xbox platforms.

He later became General Manager of Undead Labs in 2015 after acting as a liaison between Microsoft and that team for four years to bring the game State of Decay to market.