Jack was one of the founding members of the video gaming website and channel Achievement Hunter. He is well-known for his appearances in Let's Plays alongside co-founder Geoff Ramsey, as well as Gavin Free, Michael Jones, Lindsay Jones and Ryan Haywood.
Jack is a series regular on a host of Achievement Hunter shows, including VS, Things To Do In..., Theater Mode, Let's Watch and the Off Topic podcast. He is also a key part of Let's Play Live, bringing live video game performances to audiences in cities across the United States.
Outside of Achievement Hunter, Jack anchors Rooster Teeth's 24-hour livestream for charity fundraiser Extra Life, and occasionally appears in various live-action productions.
- A likeness of Jack appears in RWBY as part of the fictional group The Achieve Men, a poster for which hangs in Team RWBY's dorm room.