In 1998, Dawn was informed that Extreme Championship Wrestling (ECW) employee Buh Buh Ray Dudley was interested in bringing her into ECW. At the behest of Dudley, Psaltis traveled to the ECW Arena in Philadelphia, Pennsylvania, where ECW promoter Paul Heyman told her that he would book her for several appearances in an angle with Lance Storm. She debuted in ECW on August 28, 1998 as the manager of Storm, feuding with Chris Candido and his manager, Tammy Lynn Sytch. Although she was only supposed to have a three week role in the company, Heyman was impressed by the chemistry between Psaltis and Storm and offered her a contract, which she accepted. Psaltis created her character to be in love with Storm and clumsy rather than glamorous.

Dawn's persona pretty much struck people as being an 'airhead' who thinks she's really cute. Case in point - during the Hardcore Heaven PPV in May 1999 Dawn headed for the ring while Lance had to restrain her from walking out in the audience. It seems that Dawn had too much on her little mind and forgot to put her panties on. Of course Lance hammed it up for the cameras while he stood in front of Dawn who giggled the whole time she was putting them on.

After Storm departed ECW, Psaltis became a color commentator on ECW pay-per-views and the television series ECW on TNN. On December 3, 2000 at the Massacre on 34th Street pay-per-view, as part of a new angle, she announced that she would become the manager of the winner of the opening match pitting Simon Diamond and Swinger against Christian York and Joey Matthews. Although York and Matthews won the bout, Psaltis opted to join forces with Simon and Swinger, who she managed until ECW declared bankruptcy in April 2001.

Following the bankruptcy of ECW, she returned to the independent circuit, managing Diamond. The duo made several appearances alongside Swinger with the short lived X Wrestling Federation in November 2001. During her time on the independent circuit, she trained as a wrestler under Simon Diamond and Mikey Whipwreck. Also in 2001, Psaltis worked as a stock trader, and in 2002, she co-hosted a syndicated wrestling radio show known as the "Piledriver Rock and Wrestling Radio Show".

In April 2002, Dawn Marie began negotiating with World Wrestling Entertainment (WWE), eventually agreeing to a deal. She debuted on WWE television on the May 30 episode of SmackDown! as Vince McMahon's legal assistant. In her initial storyline, she briefly feuded with Stacy Keibler over McMahon's affections until McMahon turned over the General Management position to his daughter, Stephanie McMahon, which was followed shortly by Keibler's departure for the RAW brand.

Dawn's most high profile storyline during her first few years with the company was in 2003 when she feuded with Torrie Wilson. In the angle, she attempted to marry Wilson's real-life father Al Wilson. She also revealed that she had developed feelings for Torrie, and the two shared an on-screen kiss. Dawn even offered to cancel the wedding if Torrie would go to a hotel with her for the night. Despite this, as part of the angle, she developed feelings for Al, and the two got married on an episode of SmackDown! in their underwear. Al then, in storyline, died from a heart attack after having rigorous sex numerous times in succession on their honeymoon. In response, Wilson defeated her at No Mercy in October, then defeated her again at the Royal Rumble in 2003 in the first ever Stepmother vs. Stepdaughter match. The feud lasted approximately nine months.

Later, Dawn Marie began a second feud with Wilson. As part of the feud, the two had a match with Wilson's career on the line when the SmackDown! General Manager at the time, Kurt Angle, made the stipulation for the match at Judgment Day, which Wilson won. After being on hiatus from SmackDown! programming, Psaltis began a new storyline with Miss Jackie, involving whether she and Jackie's fiancée, Charlie Haas, had an affair. This angle led up to a match between the two at Armageddon, with Haas as the guest referee. Dawn won the match, but afterward, Haas confirmed their affair and broke off both relationships.

Dawn Marie's last appearance with the company was at ECW One Night Stand. Afterward, she was released while on maternity leave, as she had recently gotten pregnant.