Caitlin Levy
Caitlin Levy hated turbulence. She also hated sitting in coach. But here she was, en route to Miami for her first business trip as head of events for Aurora, violently jolting up and down, her gold bangles jangling, stuck in the last row of the plane. She felt like she might be sick, but the seat belt light was on, and she was nestled between a large man with hairy forearms and a college kid who’d been snoring since the moment he sat down.
This was not the fancy executive life she’d pictured when she signed her contract with Aurora two weeks ago, but she’d been late to book the flight, and business class was already full. She’d walked past her new colleagues as she’d boarded, their headphones on, computers out, already sipping champagne. None of them had even looked in her direction, which was a relief—she’d have enough time for awkward introductory chats when they arrived at the hotel.
Caitlin was traveling to Florida for Aurora’s executive retreat, an annual gathering of the company’s top employees. When Caitlin had accepted her offer, via DocuSign, Aurora’s eccentric CEO, John Shiller, replied with a one-liner: Just in time for Miami! (Not Congrats, not Welcome to the team, not We can’t wait for you to dig in!) It was obviously an important occasion, and so Caitlin had agreed to go, even though she hadn’t even officially started in her role. This was supposed to have been her time off in between jobs, which her husband, Mike, had moaned about. He was also annoyed to be left alone with the kids for four nights, so she could go “participate in bullshit team-building exercises and get drunk with her new colleagues,” as Mike snarked, but Caitlin really had no sympathy. Her son, Joey, had asked if Dad was “babysitting” while Caitlin was away.
“Your father is your father, not your babysitter!” she’d snapped, loud enough for Mike to hear in the other room. Though they both had big jobs, Caitlin, like most working women she knew, took on the familial mental load. She organized all the school stuff, doctor’s appointments, playdates, sports teams. She stayed home when someone was sick. She rearranged meetings when one of them needed her. Mike was an engaged dad, for sure, hands-on in a way Caitlin’s father had never been. Mike changed diapers, he read books before bed. He and Caitlin earned around the same amount, but his job came first. Always.
Caitlin gripped the seat as another wave of turbulence hit. She was anxious, which was unlike her. She was forty and a success (last year, she’d made it into Crain’s “40 Under 40” by the skin of her teeth). She’d been running events for large companies for nearly twenty years. She was very competitive. People she worked with called her “intense” behind her back. Once, an assistant mistakenly G-chatted her, “Caitlin needs to calm down! She’s not saving the world, she’s planning parties.” (The assistant was immediately fired.) All Caitlin’s past jobs were at known quantities: on the agency side at Edelman, then consulting for media companies like Condé Nast and Hearst, and, most recent, in-house at Viacom. They were name brands her parents and their friends would easily recognize. Aurora was not one of these, and though it had grown enormously since it launched in 2017, its newness made her jittery.
She put on her noise-canceling headphones and closed her eyes, attempting to both drown out the snoring and calm the nerves assaulting her body. Her new assistant had sent her the retreat agenda this morning. First, they’d be taken to the 1 Hotel to check in, after which everyone had been booked for a spa treatment. Caitlin had chosen an “Organic Awaken Resurfacing Facial,” which she hoped would take a year or so off her face. From 3:00 to 5:00 P.M. she could go to either the pool or the beach, or relax and catch up on emails in her room. The evening’s events started at 6:00 P.M., with cocktails at Watr, the 1’s rooftop restaurant, followed by an 8:00 P.M. dinner at ZZ’s, a private supper club in the Design District. The party continued afterward, with tables reserved at LIV, one of Miami’s most exclusive clubs. A DJ named ANZ, whom Caitlin had never heard of, was playing that night. (Why was everything in Miami composed of random letters that spelled … nothing?) Caitlin was exhausted just thinking about it.
She and Mike hardly ever went out anymore. They were so drained from work and the kids—Joey was seven, and Lucinda had just turned nine. When they met, Mike had been a creative director at Digitas, a trendy advertising company, and Caitlin was working at Condé Nast, producing marquee events like the Met Gala and Vanity Fair’s Oscar Party. They were always drinking, out dancing, dressed up and ready to go. That was then. Their lives had now flattened into forty-something routines: work, homework, weekend sports, birthday parties, school fairs. Jeans. Sneakers. Pajama pants at night. Kill yourself.
They lived in Bronxville, an expensive suburb just outside the city, and Caitlin loved their house, a light-filled, four-bedroom white Colonial. She loved Mike, mostly. She loved her children, always. She loved climbing the corporate ladder, she really did. But she was deathly bored. Was this it? Had she reached her peak? She was an executive vice president at Viacom, producing all the TV networks’ events, including the VMAs and the MTV Movie and TV Awards, plus the upfronts. It was a lucrative, respectable gig. She had power and money, and overall, it wasn’t that hard. She still had time for Joey and Lucinda, time to help plan the godforsaken school fair. She hadn’t been looking for a new job. But, as they say, that’s the best time to get one.
John had cold emailed her one day before the holidays. Not a headhunter. Not head of Aurora’s HR. The CEO himself. How he’d found her personal email, which included her married name, she didn’t know—she basically used it only for school communication and spam. The subject line was Hey. She’d been sipping tea in her pristine Shaker-style kitchen, looking out at her garden, covered in a layer of early winter frost. She opened the email.
Caitlin Levy! You are a person I’d love to meet. We have a new role here for which you’d be perfect. Events are Aurora’s future, and you can be part of that! I’m cc’ing my assistant, Madison, to set up a meeting. It’s all happening. Cheers,
John.
“Cheers”? Caitlin knew John Shiller wasn’t British, so she wasn’t sure what “cheers” was all about. She’d shown the email to Mike later that night, after the kids were in bed and they were having a glass of wine in front of the fire. It was Top Chef night, and they were both looking forward to it. Mike handed her phone back, one eyebrow raised.
“He sounds like a douchebag,” he said. He leaned back on the couch and put his feet up on the coffee table, creating smudges where his heels rubbed against the glass. It made Caitlin crazy.
“And isn’t Aurora some kind of advertising technology company? What does that have to do with events?” Mike ran his hand through his hair, which had thinned considerably over the past five years. There was a bald spot at the top of his head the size of a hockey puck. Recently, Caitlin had been having dreams in which she was cheating on Mike, always with some faceless man. The details weren’t specific—usually Caitlin was the aggressor—and she’d wake up guilty and bothered, relieved for it to be over.
“They’re not just ‘some kind’ of adtech company, they’re the adtech company,” said Caitlin, bothered that Mike wasn’t impressed that the CEO of one of the hottest startups had sought her out specifically. In truth, Caitlin had to google “adtech” after she’d received John’s email. She learned it had to do with managing internet advertisements across different channels, like search, video, and mobile, but the details were still fuzzy.
“Okay, I’ll grant you that,” said Mike. He was still at Digitas all this time later, leading their media group. Unlike Caitlin, who easily got restless, Mike was happy to stay in one place. “But why do they need someone to run events?” he asked.
Caitlin didn’t know. She hadn’t even responded to John yet. “I’m not sure, but I’m going to find out,” she said. Mike shrugged.
“Suit yourself. I’ve heard through the grapevine that John Shiller is a real blowhard. That he doesn’t know how to do anything but fundraise. But I suppose if he has the right people running the company, that’s all he needs to do. And you’d certainly be an asset to any executive team.” Mike moved over to Caitlin’s side of the couch and started to rub her shoulders, redeemed.
Caitlin’s eyes jolted open as the plane rocked to its side, the turbulence bad enough to awaken the sleepy teenager in the aisle seat. He pulled his baseball cap over his eyes and quickly fell back into it. Caitlin took out her phone and opened the pdf of the presentation she was set to give tomorrow. It needed work, but she didn’t have enough space to open her laptop; her other seatmate’s arm was nearly in her lap. The first slide said: “Events at Aurora—a New World!” on a black background. The next was an introduction to Caitlin: her headshot, bio, bullet points of her greatest accomplishments at other jobs. She’d created two additional slides, one with the header “New Events Strategy” and one with “Revenue Goals and Opportunities.” But they were currently blank, and Caitlin didn’t know how to fill them.
Though she’d chatted with John about the company and its amazing tech, she was still unclear as to what she’d be doing in her role. When she’d asked what he envisioned for events at Aurora, or similar examples he could point to, he went all blustery and weird, changing the topic and looking off into the distance.
This was hardly John’s only tic. Before her first and only meeting with him, a few weeks after he’d sent her that email, Caitlin had done some professional reconnaissance. She’d read every interview he’d given (he was a prolific talker and spoke in full paragraphs; much of what he’d predicted for the markets had come true). But she couldn’t find a single TV appearance on Bloomberg or CNBC, which must have been a purposeful choice by Aurora’s PR department. “He’s … weird” was something she heard repeated by people who’d met him. Also, some variation of “He’s very full of himself.” And most often: “He’s probably on the spectrum, just like every other tech CEO.”
Caitlin felt morbidly curious as she’d entered the lobby of the Freehand Hotel for their initial interview about this mysterious job.
John’s assistant, Madison Bez, had insisted they meet at a bar instead of at Aurora’s office; John wants this to be totally discreet, she’d emailed ominously. Caitlin had found him at a corner table, already sipping a whiskey, wearing a blue Lacoste crewneck T-shirt, bright orange pants, and white Nike sneakers. She laughed to herself about Madison’s note—if John wanted to hide, the pants certainly weren’t helping.
He stood to greet her, and she was surprised by how short he was—five foot eight, tops, smaller than she was in her heels. He went in for a hug, which Caitlin wasn’t expecting, and she instinctively recoiled, making the whole thing even more uncomfortable. It ended up as a kind of mutual back pat. John quickly sat down, motioning for Caitlin to sit next to him, making it so they were both on the same side of the small table. Caitlin was wearing a simple black sheath dress, chic but professional. Sweat was causing the wool to stick to her lower back. She hadn’t been nervous like this in ages. It felt invigorating.
“Caitlin, Caitlin, Caitlin, where do we begin?” said John. It was only 6:00 P.M., but the bar was starting to fill, and Caitlin was struck by the idea that someone she knew would walk in and think she was cheating on Mike. John’s face was very close to hers. He had a light brown beard and adjoining mustache, and narrow green eyes that illuminated an otherwise plain face. She realized he was waiting for her to answer. A pretty waitress put a Negroni in front of Caitlin. She gratefully took a large sip.
“How did you know I liked Negronis?” she asked.
John laughed. “I do my homework before I meet people,” he said.
“So do I,” she countered, feeling bold. She wondered what else he could have heard about her. She smiled at him. Was she flirting? How strange. At thirty-nine, John was a year younger than she. She knew he was unmarried and dated around, usually pictured in Getty party photos with very beautiful, very young women.
“For the most part, people gave you glowing reviews,” he said. “A few former coworkers, who shall remain nameless, called you ‘cutthroat’ and ‘overly ambitious.’” Caitlin felt herself flush. “But,” said John, “to me that’s a positive. I want you to be cutthroat if you’re on my team! All the best generals are.” Caitlin had read that John was obsessed with World War II and had spent millions on memorabilia at auction. She’d heard whispers that he owned Winston Churchill’s private wartime diary and kept it locked in a safe in his house in Miami.
Before Caitlin could ask any questions about the job, John launched into a retelling of Aurora’s origin story. Caitlin already knew the basics: John and his two best friends, Dallas Joy and Robbie Long, were rising stars in New York’s tech scene a decade ago. They’d always wanted to start a company together, but Robbie died tragically from a drug overdose before they had the chance to. Robbie had been fascinated by adtech, so John and Dallas came up with the idea for Aurora over dinner one night in Brooklyn as a tribute to Robbie. They even gave Robbie’s fiancée, Meagan Hudson, a large part of the original equity. Dallas, the engineer, developed Aurora’s amazing algorithm, and John, the genius pitchman and fundraiser, got investors excited about it. Aurora grew and grew, revolutionizing the way advertising was bought and displayed online. Six years later, Aurora had over four hundred employees, office space in New York and Miami, and was valued at half a billion dollars.
“So you see, Caitlin, there isn’t anyplace you’d rather be working now than Aurora,” said John. His green eyes flicked back and forth across her face, never quite settling into contact with hers. “I wouldn’t say this publicly, but there is no better CEO on earth than me right now.” He gave a slightly deranged smile. “Not Elon, not Tim, not Sundar, and definitely not Mark, that little pussy.”
“Well, you sure are good at selling yourself,” said Caitlin. She knew she should feel turned off by his ego (and the word “pussy”), but his bluster was having the opposite effect. She leaned in, shifting closer to him, near enough to smell his musky aftershave.
“I can sell myself, too. But I need to know what the job is first,” she said.
“All that in good time,” said John. “I had a feeling you’d be the right person to complete our executive team, and I’m happy to report that—as usual—I was right.” The meeting had continued in that way, with lots of banter but no substance. She’d left the Freehand convinced of John’s charisma but not much else. It didn’t seem like he had a baked events strategy, and Caitlin figured it was a fishing expedition rather than a real search. The feeling was confirmed when she didn’t hear from him immediately afterward.
“You wouldn’t have wanted to work for that guy, anyway,” Mike had said (he was almost too happy that it seemed to have gone bust). Caitlin had settled back into her job at Viacom, filling her days with the usual putting out fires and mediating employee spats, irritated to have wasted her time. Then, three months later, she received another email from John, this one with the subject line: Offer.
Caitlin, Caitlin, Caitlin, the email read. She was sitting at her desk at work, on the thirty-first floor of One Astor Plaza, a block from Times Square. She commuted into Manhattan three days a week, happily leaving her life in the suburbs, taking the Metro-North from Bronxville and then the shuttle from Grand Central Station. She felt in control at the office in a way that she loved, even when she wasn’t doing anything but staring at the downtown skyline. She liked wearing heels and putting on lipstick. She read on.
Here I am, back to offer you the opportunity of your lifetime. The job is head of events of Aurora. Your salary will be $2.5 million, with a discretionary bonus of $500k. You’ll get 200,000 shares to start, plus more based on your success. And I know you’ll have success! I believe in you. It truly amazes me how dumb most people are about their career choices. Please don’t disappoint me by being lumped in with that group. You’ll be hearing from Debra Foley, our chief people officer, shortly. She can walk you through details. Excited to have you on board! Cheers,
John.
Caitlin reread the email to make sure she’d seen the number correctly. Three million dollars? She thought startups only paid small salaries. Plus that much equity in the company? It must be some kind of joke. She was currently making, all in, about a million dollars a year, and that was after some serious haggling with Viacom, plus several end-of-year raises. Before she could rethink it, she’d replied, Thank you for the offer, John! But isn’t that a lot? And what will I do all day?
He pinged her back not five seconds later. I pay my generals well! And … you’ll figure it out.
After a few minutes, she’d received her first email from Debra Foley, laying out the terms of the offer and attaching a DocuSign for her to return. She’d had so many questions. She still did. But, against her better judgment and without meeting anyone else at Aurora, she’d accepted the job. Mike had been begrudgingly supportive (he kind of had to be; she’d now be earning more than three times what he did). As a couple, they’d be making around four million dollars a year—more than enough to get a cute second house in Quogue or Montauk, which Caitlin had been wanting to do for years.
The plane was finally nearing Miami. Caitlin could see the blue-green ocean leading to the gridded city, white buildings rising toward the sky, the sun reflecting off the water. The forecast for the duration of the executive retreat called for clear skies and eighty-five degrees, and Caitlin was hoping to get in some beach time between team meetings and dinners.
She looked up to see a man walking down the aisle, eyeing each row as if searching for a friend. She recognized him from his corporate headshot on Aurora’s “About Us” page: Zach Wagner, Aurora’s chief revenue officer. She’d read in his bio that he came from the world of traditional advertising, acting as chief marketing officer of several large retail brands, including Macy’s and American Eagle, before jumping to the other side and leveraging his relationships in his role at Aurora. He looked to be in his midforties, with springy black hair and a salesman’s attractive, open face. He was wearing jeans and a sports coat and cool-dad New Balances. The pilot had announced landing prep, so Caitlin assumed Zach was heading to the restroom, though she wasn’t sure why he’d come all the way back here. He stopped in front of her row and stared at her. She smiled tentatively, unsure if he knew who she was.
“Caitlin Levy? The Caitlin Levy?” Zach reached over the slumbering teen and held up his hand in front of her. Was she supposed to high-five him? She tapped his hand with her own.
“You must be Zach,” she said. “I’ve read so much about you. That was a great interview you gave in the Journal the other day.”
“Thanks! Nice to meet you!” said Zach. The plane was rocking a bit, and he held on to the seat to prevent himself from tumbling toward the bathroom. “I’m so happy you could make it on this trip. I’m sorry it’s eating into your vacation time, but I think it’s worth it. John, you’ll see, lives for the executive retreats. And I think that he has a big announcement to make tonight that you wouldn’t want to miss.” Caitlin was surprised by this news; John hadn’t mentioned anything imminently major during their interview.
“I’m glad I could come. It’ll be great to meet everyone before I officially start,” she said.
“I also know that John has huge expectations for you,” said Zach, raising his eyebrows playfully. Caitlin wondered if Zach knew about her salary. A friend of a friend had told her that Zach loved to drink and was the life of any party. She’d also heard rumors that he could be hilariously off-color, a trait that served him well in the early aughts but recently had been getting him in trouble. Apparently, he’d held an all-hands meeting to motivate his team and had shown up in a Native American headdress, complete with face paint, whooping and cheering. It was a complete HR nightmare.
Copyright © 2024 by Emma Rosenblum
