Gulak debuted as part of WWE's Cruiserweight Classic tournament on June 23, 2016, with Gulak defeating Harv Sihra in his first round match. On July 14, Gulak was eliminated from the tournament by Zack Sabre Jr.. Gulak appeared on the September 14 episode of NXT, losing to Hideo Itami. On the September 26 episode of Raw, Gulak made his main roster debut, teaming with Lince Dorado in a losing effort to Cedric Alexander and Rich Swann. On the Hell in a Cell pre-show, Gulak teamed with Tony Nese and Ariya Daivari in a losing effort to Cedric Alexander, Lince Dorado, and Sin Cara. On the Survivor Series pre-show, Gulak, Tony Nese, and Ariya Daivari lost to T.J. Perkins, Rich Swann, and Noam Dar. In December, it was confirmed that Gulak had signed with WWE. On the January 2, 2017, episode of Raw, Gulak won his first match on the main roster against Cedric Alexander.
In 2017, Gulak introduced a new gimmick in WWE, beginning to campaign for a "Better 205 Live." The campaign included Gulak asking Mustafa Ali to use a more conservative in-ring style as part of a "No-Fly Zone" campaign. This prompted a feud between the two, which ended on July 18 episode of 205 Live, when Gulak lost to Ali in a two out of three falls match. As part of his gimmick, he began incorporating his own PowerPoint Presentations every week on his plans for a better 205 Live. Gulak went on to feud with Akira Tozawa about his war cry chanting. On the October 10 episode of 205 Live, Gulak attacked Tozawa on the ramp and later injured his voice box. Tozawa gained revenge on Gulak, which led to a match on October 31 episode of 205 Live, which Tozawa won. Gulak had aligned with Enzo Amore and became a member of Amore's faction "The Zo Train", while continuing his rivalry with Tozawa. On the November 21 episode of 205 Live, Gulak lost to Tozawa in a Street Fight, ending their feud. On the December 4 episode of Raw, Gulak won a fatal four-way match to face Rich Swann the following week, with the winner earning a match against Enzo Amore for the Cruiserweight Championship. However, Swann was suspended prior to the match and replaced with Cedric Alexander. On the December 18 episode of Raw, Gulak lost to Cedric Alexander, making him unable to face Amore for the Cruiserweight Championship. On January 23, 2018, Amore was fired from WWE and Zo Train was quietly disbanded.
In February 2018, Gulak was entered into a 16-man single elimination tournament to determine a new Cruiserweight Champion, with the final round set to occur at WrestleMania 34. Gulak defeated both Tony Nese and Mark Andrews via submission en route to the semi-finals, where he lost to Mustafa Ali. During this time, Gulak stopped the PowerPoint Presentations and his "No-Fly Zone" campaign for a better 205 Live, and developed a new character with aspirations to be the best submission specialist in WWE. Around this time, Gulak formed an alliance with Gentleman Jack Gallagher and The Brian Kendrick. On the July 24 episode of 205 Live, Gulak won a fatal four-way match also involving Mustafa Ali, TJP and Hideo Itami to become the number one contender to the Cruiserweight Championship. Gulak would challenge Cedric Alexander for the Cruiserweight Championship at SummerSlam and on the September 19 episode of 205 Live, where he was unsuccessful both times.
On the October 3 episode of 205 Live, Gulak and Gallagher would attack Kendrick, citing him as the "weak link" of the team. This would lead to Kendrick allying himself with Akira Tozawa to face Gulak and Gallagher, with the two sides trading victories culminating in a Street Fight on the December 18 episode of 205 Live, where Gulak and Gallagher lost. Afterwards, Gulak and Gallagher would try to recruit Humberto Carrillo into their stable, while also trying to convince him to stop using high flying moves and a more ground based offense. Gulak competed in a tournament to determine a new challenger for Buddy Murphy at WrestleMania 35, where he defeated The Brian Kendrick in the first round, but lost to eventual winner Tony Nese in the semifinals. On the April 9, 2019 episode of 205 Live, after Gulak attacked Humberto Carrillo during his match with Gallagher, Gallagher headbutted Gulak out of the ring, thus ending their alliance.
Following April, Gulak would be taken off television and would post a series of cryptic tweets hinting at a dark turn for his character. He would return to the ring in June after his hiatus, displaying a more aggressive attitude and in-ring repertoire. In his first match back, Gulak sported all black ring gear and slicked back hair, as he attacked Noam Dar before defeating Akira Tozawa. The following week, he participated in a fatal four-way match with Tozawa, Humberto Carrillo, and Oney Lorcan to determine the number one contender for the Cruiserweight Championship, where he and Tozawa pinned each other's shoulders on the mat. Therefore, they both won the match and earned the right to face Tony Nese at Stomping Grounds in a triple threat match. At the event on June 23, Gulak pinned Tozawa to win the Cruiserweight Championship for the first time. He would then face Nese at Extreme Rules in a rematch for the title, which Gulak won. At SummerSlam, Gulak would defend his title against Oney Lorcan where he was victorious after using underhanded tactics. A few weeks later, Lorcan and Gulak would face off in a Captain's Challenge match where they both handpicked their own teammates in which Lorcan's team was victorious. At Clash of the Champions, Gulak retained the title in a triple threat match against Humberto Carrillo and Lince Dorado after pinning Dorado. Gulak lost the renamed NXT Cruiserweight Championship to Lio Rush on the October 9 episode of NXT. On the October 11 episode of 205 Live, Gulak teamed with Tony Nese against Oney Lorcan and Danny Burch in a losing effort in what would turn out to be Gulak's final match on 205 Live.
As part of the 2019 draft, Gulak was drafted to SmackDown. In his debut on the main roster, Gulak attempted to show Braun Strowman a PowerPoint Presentation on how to beat Tyson Fury, but he was quickly defeated by Strowman in a singles match. The following week, he would attempt to show a PowerPoint Presentation on how Braun Strowman can lose to Tyson Fury before his match with Kalisto, but he was once again attacked by Strowman. On the November 15 episode of SmackDown Live, Gulak, along with The B-Team (Curtis Axel and Bo Dallas) would taunt Strowman for his loss against Tyson Fury, but Strowman would attack all three men and lay them out.
In February, Gulak began a feud with Daniel Bryan after claiming to have "found holes in his game" and placed him in matches against opponents such as Heath Slater and Curtis Axel to test his weaknesses, but Bryan came out victorious. On the March 6 episode of SmackDown, Bryan challenged Gulak to a match at Elimination Chamber. At the event, Gulak lost to Bryan by technical submission. On the March 13 edition of SmackDown, Gulak agreed to teaming with Bryan, turning him face in the process. The following week, Gulak and Bryan teamed up to defeat Cesaro and Shinsuke Nakamura in a tag team match. On the March 27 episode of SmackDown, Gulak defeated Nakamura to earn Bryan an Intercontinental Championship match against Sami Zayn at WrestleMania 36. On April 4 at WrestleMania, Drew Gulak lost to Cesaro. On the April 24 episode of SmackDown, Gulak was defeated by King Corbin in a Money in the Bank qualifying match due to a distraction by Cesaro and Nakamura, who attacked Bryan at ringside and proceeded to attack him afterwards. On the May 15 episode of SmackDown, Gulak faced his mentor Bryan but was defeated in the first round of the Intercontinental Championship tournament. The following day, Gulak's contract with WWE expired after he opted not to renew it. On May 25, 2020, it was reported that Gulak was re-signed by WWE. On the May 29 episode of SmackDown, Gulak participated in his first match back for WWE, a 10-man battle royal for a spot in the WWE Intercontinental Championship tournament, but was eliminated by King Corbin. On the June 5 episode of SmackDown, Gulak defeated AJ Styles with a bridging folding press. This led to him getting an Intercontinental Championship match against Styles on the July 3 episode of SmackDown, where he was defeated. On July 17, Gulak served as a guest commentator on 205 Live alongside Vic Joseph, where he continued to provide commentary for the show until the return of Nigel McGuinness. At Clash of Champions, Gulak pinned R-Truth to become the WWE 24/7 Champion for the first time. He would lose the title back to Truth later on in the night.
As part of the 2020 draft in October, Gulak was drafted to the Raw brand. Over the following months, he kept on chasing after the 24/7 Championship, mainly feuding with R-Truth and Akira Tozawa and capturing it on several occasions, also turning into a tweener in the process. During the Survivor Series kickoff show, Gulak won the title for the seventh time as The Gobbledy Gooker; this reign is recognized by WWE as a reign for The Gobbledy Gooker, but not for Gulak.Throughout the end of the year, Gulak would continue to chase after the 24/7 Championship. On the January 11 episode of Raw, Gulak would face AJ Styles for a chance to qualify for the 2021 Royal Rumble, but was unsuccessful.
He would then mostly compete on WWE Main Event and begin a losing streak. At Fastlane, Gulak appeared in 24/7 Championship commercial. On the March 24 episode of Main Event, his losing streak finally ended when he defeated Akira Tozawa. On the April 1 episode of Main Event, he was defeated by Humberto Carrillo. After the match, they showed each other respect by shaking each other’s hand, confirming his face status. On April 22, he debuted new attire and was defeated by Lince Dorado. On the April 29 episode of Main Event, he defeated Akira Tozawa. On the May 3 episode of Raw, he returned and berated Angel Garza, saying he has no game. This led to a match between them, which he was lost, and after the match, Garza stuck a rose in his tights.
As part of the 2021 Draft, Gulak was drafted to the SmackDown brand. On the April 15, 2022 episode of SmackDown, Gulak became a backstage interviewer for the brand for a few weeks.
In December 2022, Gulak would begin appearing in NXT once again, as Hank Walker's personal trainer. On the February 14, 2023 episode of NXT, Gulak turned on Walker and aligned with his rival, Charlie Dempsey, turning heel for the first time since 2020. On the August 8 episode of NXT, Damon Kemp assisted Gulak and Dempsey win a match against Josh Briggs and Brooks Jensen, officially joining the team. On the September 12 episode of NXT, during a six-man tag match, Myles Borne betrayed both Briggs and Jensen and turned heel, joining the team of Gulak, Dempsey and Kemp as the fourth member of the newly-dubbed No Quarter Catch Crew. On the February 27, 2024 episode of NXT, Dempsey defeated The Meta-Four's Noam Dar 2–1 under British Rounds Rules for the NXT Heritage Cup. A week later at NXT Roadblock, NQCC announced that the NXT Heritage Cup would be defended by the whole stable under the "Catch Clause". The Catch Clause was invoked on the March 19 episode of NXT, with Gulak defeating Chase University's Riley Osborne 2–1 to successfully defend the Cup after interference from Jacy Jayne and Jazmyn Nyx. On May 3, Gulak was released from WWE.