|Portrayed by||Peyton List|
|First appearance||The New Girl|
|Employer||Sterling Cooper Advertising Agency (former)|
|Occupation||Don Draper's Secretary (Quit)|
|Other Relations||Danny Siegel (cousin)|
Jane Sterling (née Siegel) is Roger Sterling's second ex-wife.
She was a college graduate who quickly caught the eye of Roger after being hired as Don Draper's secretary. After Joan Harris fired Jane for flouting company protocol, Roger smoothed things over with the fiery red-headed office manager. Once rehired, she began an affair with Roger which ultimately led to their marriage.
While Don's secretary, Jane deduced something was amiss after receiving a phone call from Don's daughter, and hoped that Don noticed that she was discreet about it. Don responded that he did not know her at all and that the issue was personal, shutting down her advances. The next day she bought shirts from Menken's, thinking that he could use some additional shirts in his rotation.
After Don talks to Roger about mostly feeling relieved about being separated from his wife, Roger tells his wife, Mona that he was moving forward with his life and leaving her for Jane. When Mona stormed out, Jane broke into tears and Roger quickly came to comfort her. Pointing to Jane, Don said to Roger, "I want her off my desk."
Jane would spend time with Roger at the Sherry-Netherland hotel. One day she told him that their souls are the same age, moments later Roger proposed to her, which she accepted.
After Jane and Roger married between seasons two and three, Jane dropped in for a visit at the Sterling Cooper offices, flaunting her new status in front of her former colleagues, particularly Joan. At a country club party hosted by Roger to help Jane gain favor with "his" crowd, Jane becomes wildly drunk, and inadvertently expresses her frustration at not being accepted. "You don't like me," she tells Don. "I'm a nice person."
On the way to Sterling Cooper's 40th Anniversary, Roger's mother confused Jane with his daughter Margaret. Roger corrects her, after which she asks, "Does Mona know?" Jane coldly responded, "Yes, she does." 
Roger's daughter Margaret was agitated by Jane's attempts to befriend her, and told Roger that she did not want Jane to attend her wedding. When Roger sees Jane, he tells her that she's screwing things up, she is upset because she believes that Roger won't take her side. Jane again asserts. "I don't know what kind of world you live in, but I am the good person here." After John F. Kennedy was assassinated, she spent most of her time in the kitchen of the reception hall during the wedding reception.
In season four, Jane is not happy that she is forced to dance with Lee Garner, Jr., who openly gropes her during the Sterling Cooper Draper Pryce Christmas party. After Roger later bungles the Lucky Strike account, he returns home. Jane greets him and has him open a box which contains copies of his memoirs.
Jane has a cousin, Danny Siegel, who she pressures Roger to find employment for. After being reluctantly hired by Don, Danny is eventually laid off with numerous co-workers, after the loss of the Lucky Strike account.
In the premiere episode of of season five, Roger and Jane are shown bickering before and during Don's surprise 40th birthday party. After Don's new wife, Megan, performs a sexy musical performance, Roger openly congratulates Don, saying, "As a wise man once said, ' The only thing worse than not getting what you want is someone else getting it.'" Jane is seen reacting to this comment with an unhappy glance at Roger.
Later in season five, Jane and Roger took LSD together. Roger's hallucinations during the acid trip lead to their divorce. The breakdown of their marriage saddens Jane greatly.
Roger openly mocks Jane's intelligence, joking about her fascination with the Texas Schoolbook Depository after the Kennedy assassination, and later telling Don, ”Two weeks ago, she asked me, ”Which one's Mussolini?””