McMahon began appearing regularly on-air for WWE (then WWF as the World Wrestling Federation) in 1999 as a part of a storyline with The Undertaker.

She returned to regular on-air appearances in 2013, this time under the gimmick of an unctuous, judgmental, bullying owner along with on-screen chief operating officer Triple H. They became a power couple and formed the stable The Authority, making what were often shady decrees while claiming only to be concerned for "what's best for business", all the while romanticizing each other in the process with public displays of affection.

McMahon's business career began as an account executive for the WWF offices in New York, before becoming the company's head writer and director of creative writing.

She oversaw all aspects of talent management and branding, live event booking and marketing, and all social and digital media properties.

She was also able to launch a huge partnership with the USO metropolitan Washington, the social media company Tout, and was able to partner with Yahoo to bring WWE content.

[33] The Undertaker stalked and abducted McMahon at the end of the April Backlash pay-per-view, which culminated in him almost marrying her in the middle of the ring the next night on Raw, before being rescued by Stone Cold Steve Austin.

McMahon confronted Vince the next night on Raw and revealed the wedding was a planned event, which was a revenge plot against her father for the aforementioned kidnappings, thus turning her heel for the first time in her career.

[50][51] McMahon later revealed that she had purchased Extreme Championship Wrestling (ECW) and intended to bankrupt the WWF (in reality, the ownership of ECW assets at this time was highly disputed), along with her brother Shane, who had become the on-screen owner of World Championship Wrestling (WCW), and the two rosters merged to form a "supergroup" known as The Alliance.

[35][53] Her team The Alliance consisting of her brother Shane, former WCW Champion Booker T, Rob Van Dam, Kurt Angle and Stone Cold Steve Austin were defeated by Team WWF consisting of The Undertaker, Kane, Big Show, Chris Jericho and The Rock at Survivor Series in a five-on-five, Winner Takes All elimination match.

[39] As part of the storyline, the couple "divorced" after McMahon claimed to be pregnant to trick Triple H into renewing their marital vows.

[67] McMahon lost when Linda, at ringside threw in a towel on her behalf because Vince did not release a choke he had on her with a lead pipe.

[69] McMahon returned as a villainess once again on October 3, 2005, for Raw Homecoming, where she confronted Stone Cold Steve Austin and received a Stunner.

[71] A visibly pregnant McMahon also returned on the March 6, 2006, episode of Raw, approaching Shawn Michaels backstage and claiming to have abdominal pains.

[72] McMahon also appeared at the WWE Hall of Fame induction ceremony on April 1, 2006, and in a backstage vignette with her immediate family at WrestleMania 22.

[83] After Adamle stepped down as general manager, McMahon soon became in charge of the brand and (reignited her feud) by having altercations with Chris Jericho in the following weeks, which involved her firing him (although he was later reinstated).

McMahon appeared on the November 1 episode of Raw in a pre-taped segment, where she dreamt that Vince awoke from a coma after his doctor, played by actor and one-time WWE employee Freddie Prinze Jr., informed him that his wife Linda had invested millions in her campaign as she runs for senate.

[6] After beginning to feel better, Vince realizes that he has a serious case of "the runs", in which he gets out of bed and walks to the bathroom, in which he is covered in campaign signs, that block his backside.

"[6] On July 23, 2012, McMahon made an appearance on the 1000th episode of Raw where she confronted and then slapped Paul Heyman to convince him to accept a match between Brock Lesnar and Triple H at SummerSlam.

[95] On the June 23 episode of Raw, Vickie lost in a pudding match against McMahon with her job on the line, after interference by Alicia Fox, Layla and Rosa Mendes.

On the December 29 episode of Raw, The Authority was brought back in power by John Cena, and she and her husband entered and stepped on the entrance ramp celebrating their return with a glass of champagne and a kiss.

Before she could start her acceptance speech, Shane McMahon returned for the first time since 2009 and demanded to gain control of Raw, claiming The Authority was running the company to the ground.

In April, Stephanie was written out of the storyline after being pushed accidentally through a table at WrestleMania 33 by Triple H, and did not appear on WWE TV for many months.

On the July 23 episode of Raw, McMahon returned to announce a match between Kevin Owens and Braun Strowman at the August 19 SummerSlam Pay Per View.

On the September 24 edition of Raw, Stephanie returned as a face for the first time since 2013 when she told Baron Corbin about the lack of leadership he had been doing and if he doesn't improve that she would bring back Kurt Angle from vacation.

On July 22, 2022, upon her appointment as the permanent chairwoman of WWE following her father Vince's retirement, she returned on the following episode of SmackDown to thank the fans for their support on social media.

In May 2000, Stephanie appeared at the WBCN River Rave on-stage with friend, Cali, to introduce Godsmack and sign autographs in the festival area.

In November 2001, McMahon appeared on a special episode of NBC's The Weakest Link where WWF personalities competed against each other for their respective charities.

[113] She has also participated in a celebrity edition of the CBS reality series Undercover Boss, disguised as a new employee just starting out in the WWE business office.

The couple were engaged on Valentine's Day in 2003 and were married on October 25, 2003, in a Roman Catholic ceremony at St. Teresa of Avila Church in Sleepy Hollow, New York.

Additionally, Adweek has included her in their list of the Most Powerful Women in Sports for the past five years and previously chose her as a 2019 Brand Genius honore.