Jan is initially the Vice President of Northeast Sales at paper distribution company Dunder Mifflin, and directly supervises Scranton branch manager Michael Scott. In season two, she enters a dysfunctional relationship with Michael, which last until season four. Michael and Jan's personas contrast to much humor in the series, particularly in their professional attitudes and social interactions, although Jan's erratic and sexually-domineering mental state of mind leads to her firing.
Jan Levinson-Gould as Vice President has a no-nonsense management style that is at odds with Michael's more casual approach. Since her office is in New York, Jan's contact with the Scranton branch is largely by telephone, although she will make the two-and-a-half-hour drive to Scranton if necessary. She usually asks if she's on camera when talking to Michael on the speaker phone, and Michael often lies and tells her she is not, before admitting that they are—at which point she hangs up on him. While initially based on Jennifer Taylor-Clarke from the UK version, her character develops in a different direction.
She smokes in stressful situations and indulges in self-destructive tendencies with poor judgment in spite of her inherent competence and professional attitude. She demonstrates a strong and often fetishist sexuality which sometimes intimidates Michael, such as when he revealed in "Women's Appreciation" that Jan did not always abide by their safety word "foliage". It is implied that she may have taken the virginity of her assistant, Hunter, of whom Michael is jealous.
Seasons 1 - 2
Jan is first introduced in the pilot episode. As Vice President, her authority leads her to inform Scranton branch manager Michael Scott of the impending downsizing or closure his branch faces. Over the rest of the series, she appears either in person or over the phone to assert corporate policy on Michael, specifically with health care plans, sexual harassment concerns, and downsizing.
Her character is expanded upon, and changes in tone during one episode, at which Michael and she attend a business meeting at a Chili's with a highly-valuable potential client. References to her seeing a psychiatrist following a difficult divorce after her lover did not want to have children and a case of identity theft are made. The end of the episode portrays her having an intimate moment with Michael. Michael's attempts at a meaningful relationship stemming from that night are rejected, however Jan open-endedly says that she is not ready for a relationship. Her appearances in the second season during a 'women in the workplace' seminar, and a financial presentation with CFO David Wallace continue this rejection, despite Michael's advances. However, upon being invited by Michael to the company casino night, she is emotionally hurt by the presence of his other date, Carol Stills , and hastily leaves; an overnight bag in her car is seen. It is highly implied Jan has developed feelings for Michael.
In the third season opener, Jan becomes responsible for the transfer of Jim Halpert to the Stamford branch, as well as negotiating a three month paid vacation and company car for accountant Oscar Martinez after Michael ignorantly outs him. Jan's next encounter with Michael is at a convention in Philadelphia, although she plays a more pivotal role when Dwight Schrute contacts her in an attempt to be promoted to branch manager at Michael's expense, a proposal which she rejects. In "Grief Counseling", Jan instructs Pam Beesly to keep note of Michael's activities after he faces grief over the death of the branch manager he replaced.
After several episodes referring to downsizing, it ultimately leads to Jan planning to merge Scranton into Stamford, with some employees being laid off and the rest transferred- her plans are frustrated when Josh Porter, whom she planned on becoming the manager of the merged branches, leverages the position with Staples into a senior management position there. This development influences Jan into merging Stamford in with Scranton instead.
Following a Christmas party, Michael calls an unnamed woman to invite her into Sandals Resort Jamaica. The woman is revealed to be Jan when Michael accidentally forwards a risqué photo of her tanning to the rest of the office, although she herself didn't receive the email. The relationship between Jan and Michael becomes official when David Wallace hosts a cocktail party. The duo attend as a couple after disclosing their relationship to HR; Michael immediately declaring loudly "I love this woman!" shortly after. Jan demonstrates a sexually aggressive attitude and indifference toward the party itself during the course of the episode. Michael defences their relationship when he attempts to negotiate a 12% pay rise with Jan.
When Michael has a "women's appreciation day", his conversations with the office women lead him to discuss Jan's radical sexual preferences, including recording their intimacy and playing it with a therapist to improve "his form." He realizes his unhappiness with her and breaks up. In the season finale, during which Michael interviews for a corporate position, Jan attempts a reunion. Michael, despite urgings from all women Scranton in the office (except Meredith, from whom Michael declined to seek advice) to the contrary, and in his amazement at Jan's breast augmentation, agrees to get back together with Jan. Unfortunately, the corporate position for which Michael, Jim, and Karen are interviewing is Jan's; after being absent from work, abusing corporate policies, and being in Scranton far too often, Jan is fired and escorted from the building in New York, and is replaced by Ryan Howard.
Seasons 4 - 5
Season four has Jan moving into Michael's condo and starting a scented candle business. Her spending drains Michael's resources, leading to a brief scheme in which Michael attempts to escape his troubles by leaving town. She also sues Dunder Mifflin, claiming wrongful dismissal, largely over her breast implants, although Michael is betrayed by Jan, who uses his private diary as evidence that the company mistreats its employees, and also learning that she gave him a scathing performance review while they were dating. In response, Michael sides with the company in the dispute, straining their relationship. Following this, during a dinner party, the two fight over each other's eccentricities and Jan throws a Dundie Award at his cheap plasma television before breaking down and nearly being arrested on a destruction of property charge. The two split up, Michael leaving with Dwight, and staying at Schrute Farms a few weeks until Jan packed up her things (mostly Michael's it turns out) and moves away for good.
Jan is seen again in the fourth season finale, in which she is revealed to be pregnant via artificial insemination. Although initially agreeing to help her with the child by joining her for Lamaze classes, Michael genuinely tries, but feels no real connection to the child, Astrid, at the office baby shower. Jan also insists Michael not go out with Holly, leading Michael to promptly and successfully ask Holly out on a date.
Seasons 7 - 9
Jan is not seen again until the seventh season, by which time she is employed as a hospital administrator, raises Astrid as a single mother and has recorded a Doris Day cover album. She tells him at great length that they were never a good couple and she was slumming by ever dating him; an angry Michael shocks her by saying (wrongly as it turned out) that he has herpes, and later expresses disbelief that he thought she could have been "the one". She reappeared on the show in a cameo scene in Michael's self-produced movie "Threat Level Midnight", playing a covert agent jazz singer named Jasmine Windsong who slips key information to Agent Michael Scarn and gets killed by an assassin. When the documentary crew approaches Jan about the movie, she pretends to be proud of Michael's finished film, and looks disgusted as she makes a hasty attempt to get her dry cleaning into her car and get away from both the cameras and any mention of Michael. Jan did not appear in the eighth season.
In the ninth season episode "The Whale", Jan is now back in Scranton, working as an executive at the White Pages phone book company. Dwight and Pam make the sales call in her office, initially unaware that she is the contact. Jan had no intention of giving Dunder-Mifflin her business, and had intended to refuse David Wallace (now the owner and CEO of Dunder-Mifflin) personally in retaliation for firing her several years before, and was dismayed when Dwight and Pam arrived instead.
Nevertheless, Dwight keeps her from refusing by assigning Customer Service representative Clark Green as her personal liaison. The two hit it off and travel abroad for several weeks. In "Suit Warehouse", Clark returns to the office, having gotten Jan to sign on as a client after spending several weeks in Europe as her lover. He compared sex with Jan to sex with "a swarm of bees... bees that just find something wrong with every hotel room". Jan also sent an expensive Italian-made espresso machine back with Clark as a gift to the staff.
In Jan's final appearance on the show (albeit over the phone) "Couples Discount", Andy Bernard (now the Scranton regional manager), points out that Dwight had offered a discounted price without getting Andy's approval (something that would've been impossible for Dwight to do, as Andy himself was abroad at the time), and attempted to renegotiate Dunder-Mifflin's contract with the White Pages. This causes an infuriated Jan proceeds to terminate her contract with Dunder-Mifflin altogether.