Previous to NIN, Woolley was a major collaborator along with former NIN drummer Chris Vrenna to Chicago band Die Warzau.
Subsequent to NIN, Woolley made contributions to Die Warzau albums again, particularly 2005's Convenience album. In 1998, Woolley toured with Rob Halford's band Two, which also included John 5 of Marilyn Manson. With Two, Woolley played live keyboards and did quite a bit of vocals as well. After Two, Woolley did some studio audio work in L.A. By 2005, Woolley had relocated to Chicago and has been involved in a new band V.O.I.D., whose long-awaited album "Mass Distraction" WILL RELEASE IN 2021! The band includes Woolley, Jon Roberts and DJ Aaron Chase of fuse, and Mark Pearlman.