Chapter Text
“Just so you know, this isn’t a diversity hire.”
Jess blinked widely at the man before her—not just any man, Kendall Roy, the future CEO of Waystar Royco. She found herself at a loss for words, not knowing this would be merely the first of a million times she found herself speechless at the pure idiocy and unhinged nature of Kendall Roy.
“I am aware.”
To be perfectly frank, Jess Jordan did not think the executive assistant position was a ‘diversity hire’—but she knew the culture of Waystar Royco. She remained keenly aware she did not fit the mold of the typical employee. Yet, she learned to ignore these little details early on, forgive the status quo, and move forward. Keep moving forward and, perhaps, keep her head down while she was at it and perform better than anyone else in the room. She did so throughout her academic career, graduating college summa cum laude, and continued to do so with any job she landed during that after graduation slump.
Jess did not know what to think when she’d been plucked from marketing on the tenth floor and been offered to interview for an executive-level assistant position. These kinds of things did not randomly happen to her; hell, she never won a scratcher, a raffle, or any type of game of luck. She was only in the marketing internship program at the conglomerate because three interns dropped out before the first day, and she’d been that third name on the waitlist.
Not even the first. The third .
She took what she could get and ran with it. After moving to the city with a dual degree in English and Communications under her belt, Jess applied for every publishing internship under the sun. The plan was to intern at a publishing house, move up in the ranks and become an editor one day.
The ominous, dreamlike fairytale of one day.
Except after receiving rejection letter after rejection letter…her plan shifted to finding an internship where she could at least put some of her degree to use. Her parents spent a pretty penny (as well as a grave of debt) on her education; she felt the slightest bit obligated to do so.
So for the last year, she kept her head down, pushed papers, and answered to her superiors with the utmost respect. She moved from an internship to a full-time position as an assistant to the head of the social media marketing division, Jackie Aldridge.
Apparently, that significant and sudden move caught someone’s eye at the executive level.
From being an assistant in marketing for less than three months, Jess found herself in a round of never-ending interviews. One after another, their questions mad-libbed together and echoed one another. First with a panel of randomly selected long-standing employees of the company, followed by another with two executive-level assistants, then with the company’s general counsel, Gerri Kellman, before meeting with the said executive she’d be assisting.
An executive, the interviewers, left blind until Mrs. Kellman informed her Kendall Roy would meet with her shortly for a brief interview before a meeting that afternoon.
“Good,” Kendall nodded, arms crossed over his chest, “glad we are on the same page here.” He wasn’t sitting behind his desk, more so casually lounging back against the edge at the front while Jess refrained from shifting in the leather club chair he offered to her. “I’m looking for a new assistant since the last one….” He trailed off, wincing. “She did not quite understand the level of discretion this job pertains.”
Jess heard from the rumor-mill Andie Myers, Kendall’s previous assistant, ran a ‘finsta’ account where she ranted about the Roys. When she scrolled through her Instagram, the account was always suggested to her, but Jess never dared to request to follow. A healthy fear of one’s boss was necessary, and it seemed Andie lacked such a survival skill. And common sense, considering the woman signed NDAs, the company would not fail to follow through with legal action if given the opportunity.
“And you think I have the ability to exhibit discretion?”
“I don’t know,” Kendall offered, brutally honest. “You could be shit at this for all I fucking know. But whoever is my next assistant cannot be because I’ve had a revolving door of incompetent women, men, and all in between walk into this office, and I really don’t need to be worrying about if my assistant is going to send a fucking email or come in with my morning coffee when I have plenty of other executive-level shit to take care of.” Jess refrained from flinching at his language; she’d heard worse from her fellow interns, but that did not mean Kendall was any less jarring. “I want to hire someone within the company and who is not looking to climb the social or career ladder.” He picked up a piece of paper from his desk. “In other words, I am looking for someone who isn’t going to fuck me when I least expect it.”
Loyalty . Kendall Roy wanted simple loyalty. Perhaps something he did not receive readily amongst his colleagues.
He just didn’t say it in those terms, but those terms were laid out in his own defensive language.
Jess did not shrink at his stern, unflinching stare. She met his gaze fully, undaunted by his arrogance.
“Based on what Jackie—,”Jess’ supervisor who sighed at every little pesky problem in the office, like it was her job to sigh with such reverence and volume instead of run her division of marketing like a well-oiled machine, “—sent me, you are punctual, follow through all your assigned tasks in a timely fashion, and are overall…forgettable. Another name to add to the long list of high performing recent grads who want to work here. Nothing too special.”
The paper dropped back down on his desk with a soft plop .
Well then. Nice to know her time in marketing was absolutely forgettable. An underwhelming presence to the point her supervisor felt the need to include when she wrote up an evaluation to send to an executive. So forgettable, even Kendall Roy agreed, finding her resume unremarkable too.
“I want someone forgettable,” he told her, blunt in the way the business men in New York only seemed to be. “A fly on the wall. You seem like someone who can do that. I need someone who can be my eyes and ears in the company, but remain faceless all the same.” He stood up straight, dusting off invisible dirt from his suit jacket. His nose twitched into a near involuntary sniff-scrunch. “I had someone look into you.”
Her throat dried at the clear breach in privacy. Yet she did not let her annoyance be known; she learned how to master her poker face at a young age. When your family moved year after year due to a parent’s work, one learned how to keep their mouth shut at any little bit of dissatisfaction.
Not to mention it was difficult to be upset with someone when they spoke so plainly and unbothered. Like Kendall Roy.
“Military kid. Mom and Dad in the Air Force. Currently stationed in California.” Hands in his pockets, he lightly paced in front of his desk as he dragged out the little, nonsensical details of her life. “Second eldest child of four. Got a younger brother and sister—like me,” he added with a chuckle, pointing to himself. “With a family like that, it must mean you know a thing or two about leaving on a moment’s notice.” She did. One year her family moved four times in seven months. This was naturally during her middle school years, arguably the most emotional time of a young girls life with first crushes, periods, and changes. Not until all the lights in the house were out did she allow herself to cry into her pillow, where no one, not even her sister on the top bunk of their bunk beds could hear her. “Clean record. High level of praise from your previous employers and references. No attachments to show—no significant other, no children, and no friends.”
In Jess’ defense, she was still relatively new to the city and making friends had never been her strong suit. Instead of embracing the young life of the city, she became the kind and polite face in passing her colleagues expected her to be. It was easy to play the part of quiet new girl even when she was no longer the quiet new girl and becoming one with the Manhattan and Waystar Royco scenery.
Kendall paused his pacing, choosing to sit in the matching club seat beside Jess. He sniffed again. A tiny twitch of the nose. “Jess, I think you and I are a lot alike.”
No. They were not. Far from it.
For one, Kendall Roy was the heir apparent to the largest conglomerate in the world. A billionaire. Second, he was a white man who perhaps been handed all he wanted in life on a silver platter. Third…
Third, he was an addict.
Jess knew that twitch of the nose. The antsy pacing, inability to sit down. The gleam of manic in his eyes before the horrid crash was doomed to come.
Her older brother, the one Kendall did not seem to mention despite doing his apparent research on her, was an addict. Had three stints in rehab. After years of falling on and off the wagon, her brother Cole was finally getting better. Last she’d heard of her brother, he got into weightlifting and was looking into becoming a personal trainer. He wasn’t using anymore, so there was that.
“How so?” Jess dared to ask. She listened rather than spoke for the majority of the interview, but that seemed to Kendall’s intent. He was a man who liked the sound of his own voice, an unsurprising revelation.
“You and I are cut from the same cloth.” Okay, not a direct answer to the question. Kendall did not seem to like direct questions, especially ones of his judgement. “An older sibling trying to do their best, wanting to put their best work out there, make their parents proud.” He paused. “I am sure your family was not too pleased to find out their daughter was pursing a degree in English,” he snorted at the idea of such a degree— wonderful , “ and moving to New York, rather than following the family business.”
A true observation; her father wanted her to go to medical school and become a doctor in the Air Force. Her mother wanted her to become a military therapist, understanding better than her husband that their daughter was not necessarily one to go out in the field of duty.
Jess did neither.
“But you are going to prove them wrong,” Kendall told her. “You are going to become my right hand woman, the executive assistant to the soon to be appointed COO.”
That sounded…
Exciting, horrifying, and all together daunting.
Yet…she did not apply for this job, nor did she really want this position. She did not care to become an assistant to an executive. Her time at Waystar Royco was meant to be temporary. But for some obscure reason, this opportunity landed on her lap, and for once Jess wasn’t having to bust her ass off to prove herself to anyone. To prove herself to her superiors, her family, herself.
Because Kendall Roy wanted her to be his fly on the wall, his hidden eyes and ears, and follow him like a diligent little soldier he expected her to be.
She heard enough whispers about the Roys. Seen them in passing in the building. Enough of the employees talked, enough revealed the ruthless nature of Logan Roy and his hapless, dauntless heirs.
Part of her wondered if Kendall Roy was necessarily a man she’d willing follow into corporate battle. Another part knew she’d be an idiot to turn down the offer.
“As much as I appreciate the offer, please understand I am going to need some time to think about this.” A simple, diplomatic answer.
“You have until the end of the week.” They were Wednesday. Only a day and a half to make a decision. Kendall stood from his chair, offering what he perhaps assumed to be a charming smile. “If I were you, I’d pack up your desk on the tenth floor. HR will send over the required paperwork, as well as the NDAs. If you need a lawyer to look over them, I can send you a guy.”
Send her a guy? “I can hire a lawyer, Mr. Roy.”
“Don’t worry about it,” Kendall told her. “I’ll pay for it. I’m taking care of you, Jess. This is how it is when you are in my corner.”
His phone rang, Kendall picking it up and dismissing her with a turn of his back.
Don’t worry about it. I’m taking care of you. Oh how often that phrase would be thrown around, from both of them. But neither were too sure how deep the other meant it.