In November 1998 in the World Wrestling Federation (WWF), Al Snow, Bob Holly and Scorpio united and formed the J.O.B. Squad. Soon after their formation, Holly and Scorpio defeated Too Much in the Squad's first match on the November 8 episode of Sunday Night Heat. On the November 22 episode of Raw is War, The J.O.B. Squad helped Mankind defeat Ken Shamrock and Big Boss Man in a triple threat match. After helping Mankind, The J.O.B. Squad gained a new member in Duane Gill, who then scored an upset over Christian by winning the WWF Light Heavyweight Championship. The Squad would score another upset later on in the night as they defeated The New Age Outlaws after interference from Shamrock, Boss Man, Mankind and other J.O.B. Squad members. Gill was later renamed Gillberg, and he began parodying the mannerisms and ring entrance style of then-WCW World Heavyweight Champion Goldberg. On the November 29 episode of Sunday Night Heat, Gillberg faced Christian in a rematch for the Light Heavyweight Championship, but the match ended in a double disqualification after the debuting Blue Meanie, a new member of The J.O.B. Squad, interfered. On the following episode of Raw is War, Gillberg scored another upset when he defeated Marc Mero, who had to retire from wrestling if he lost.
On December 13 at Rock Bottom, Gillberg defeated Matt Hardy to retain the Light Heavyweight Championship on an episode of Sunday Night Heat. However, The Brood defeated Snow, Scorpio, and Holly on the pay-per-view. A month later at the Royal Rumble, Blue Meanie, Snow, and Gillberg were each eliminated from the Royal Rumble match within a span of ten seconds.
In February 1999, Scorpio was released by the WWF while Gillberg was later phased out of storylines. After dwindling down to only two members, Snow wrestled against himself on an episode of Raw is War before Holly came down to the ring to prevent Snow from hurting himself. Later that month at St. Valentine's Day Massacre, Bob Holly defeated Snow for the Hardcore Championship to permanently end The J.O.B. Squad.