Uncanny Valley

by Anna Wiener

  “Look up sick systems,” said Noah. “Look up trauma bonding. It’s the culty thing: keep people busy until they forget about the parts of their life they left behind.”

  We all knew that the CEO had his own demons. He had to be full of pain and fear like anyone else. He threw around the word “paranoid,” but of course he was at least a little bit paranoid—how could he not be? He probably wondered, every day, when the other shoe was going to drop; when everything he touched would stop turning to gold.

  I was reluctant to entertain the idea that the CEO was egomaniacal or vindictive. I liked him. There was something familiar about him that was comforting. He reminded me of my high school classmates from a math-and-science magnet in Manhattan: boys who were mathematically brilliant and slightly socially awkward, encouraged but underestimated, and, in almost every case, subject to an unbelievable amount of pressure. I liked that he had an enthusiasm for technology, understanding how things worked. It wasn’t about the money for him, I was sure. It was about making something people valued, solving a new problem, getting it right. I assumed he had his reasons, something to prove. An unknown email address was bcc’d on all our support tickets; the solutions manager intimated that it belonged to the CEO’s mother.

  In any case, I had always appreciated people whose praise and affection were hard-won. I assumed the CEO’s reticence indicated he meant what he said. I assumed everyone was doing the best that they could. I wasn’t, at the time, thinking about power, manipulation, or control.

  I felt very protective of the CEO—or, at least, of my idea of him. For a long time, I would harbor a free-floating sympathy for people I imagined hadn’t had the opportunity to experience their youth the way I had. He never had space to fuck up. He’d been under pressure—and a certain degree of surveillance—from venture capitalists and journalists and industry peers since he was twenty. At the age when I was getting drunk with friends on bottles of three-dollar merlot and stumbling into concerts, splitting clove cigarettes and going to slam-poetry open mics, he was worrying about headcount, reading up on unit economics. I was exploring my sexuality; he was comparing health insurance providers and running security audits. Now, at twenty-five, he was responsible for other adults’ livelihoods. Some of my coworkers had families, even if they tried not to talk too much about their children in the office. Surely, he felt that weight.

  It would take me a while to realize how rarefied the CEO’s world was. He was surrounded by people who were crushing it, and people who had chosen him. Kingmakers. People who did not like to admit defeat. The CEO’s community was the business community, and it would take care of him. He wasn’t in peril. Even if the company was a failure, he could easily fund-raise for a new one, or, in the worst-case scenario, become a VC. Unlike the rest of us, he could never backslide.

  When the CEO’s family came to visit, he toured them through the office quickly. Your parents must be really proud of you, I said, as he came back to our cluster to answer emails. I knew that sentimentality was not his preferred emotional register. I knew I was being too tender, but I couldn’t help it—I felt a deep compassion toward him. I was proud of him—though I kept that to myself.

  The CEO only shrugged. “Maybe,” he said.

  * * *

  Noah had been with the startup for a year, and was preparing for his annual review. In advance of the meeting, he sent me his self-assessment and a memo he had written, asking for feedback. As an early, well-respected employee, Noah was often the recipient of grievances and concerns from teammates and customers. In the memo, these came to a head: he agitated for changes to the product and changes in the company culture.

  He also agitated for himself: for a title change, more autonomy, a raise, and an increase in stock options. He wanted equity commensurate with his contributions, about 1 percent of the company. Noah presented the data: the number of hires he’d referred, the accounts he—and his referrals—had acquired and nurtured, the amount of money he calculated he had generated for the company, both directly and indirectly. He wanted to become a product manager, to run his own team, and to override the CEO on any related decisions. He framed it as an ultimatum.

  Offering the chief executive an ultimatum was unprofessional, crazy, even for one of the best employees at the company. On the other hand, it was a company of twentysomethings run by twentysomethings. The CEO had never had a full-time job; he had only ever held a summer internship. The work environment was one where offering an ultimatum seemed within the bounds of acceptable behavior. It was an incredibly strange place to learn how to be a professional.

  The memo was passionate; it radiated frustration. I read through it twice. Then I wrote back to Noah and told him what I believed to be true: it was risky, but it wasn’t unreasonable. I hoped they would give him whatever he wanted.

  * * *

  A few days later, en route to work, I received a text message from Noah, telling me he had been fired. When I got to the office, the cluster felt like a funeral home. “They didn’t even try to negotiate with him,” a sales engineer said in disbelief. “Not a single negotiation. They just let go of one of our best people, all because nobody here has any management experience.”

  “I don’t know,” the account manager said, buttering his toast. “You know how, when you want to break up with someone, you twist and turn until they break up with you?” I did not. I thought about how I had signed off on Noah’s memo and felt nauseous with guilt.

  Previous firings had catalyzed company-wide emails with what was probably an inappropriate level of detail about why the team member had been let go. In lieu of an email, the early members of the Solutions team were corralled into an unscheduled meeting with the CEO. None of us should have been privy to someone else’s personnel issue, but we didn’t have a Human Resources department. Besides, we wanted to know. We all wondered whether one of us would be next.

  The CEO told us to sit down. We sat. He stood at the front of the room, arms folded. “If you disagree with my decision to fire him, I’m inviting you to hand in your resignation,” he said, speaking slowly, as if he had rehearsed. He looked around the table, addressing each of us individually.

  “Do you disagree with my decision?” he asked the account manager.

  “No,” the account manager said, raising his palms as if at gunpoint.

  “Do you disagree with my decision?” the CEO asked the sales engineer.

  “No,” the sales engineer said. His eyelids fluttered. He looked ill.

  “Do you disagree with my decision?” the CEO asked me. No, I said. But I did disagree; obviously, I disagreed. Whenever I wondered whether I had made the wrong decision, switching into the tech industry, Noah had served as my control. Discontent across the company was high, true—but I regularly looked around, saw him, and thought: It can’t be that bad if he’s still here.

  After the meeting, we simmered in our unease. The job market was in our favor, we joked; better to get out while the company still looked good on our résumés. We brought a renewed commitment to our customer emails. We kept out of the way.

  In the evening, some of us got ourselves out of the office and into a bar. We speculated about our job security, complaining about the bureaucratic double-downs, casting blame for roadblocks and poor product decisions. We talked about our IPO like it was the deus ex machina coming down from on high to save us—like it was an inevitability, like our stock options would lift us out of our existential dread. Realistically, we knew it could be years before an IPO, if we were bound for an IPO at all; we knew in our hearts that money was a salve, not a solution.

  We were starting to realize that we had been swimming in the Kool-Aid; we were coming up for air. We were lucky and in thrall and then, unseen to us, we had become bureaucrats, punching at our computers, making other people—some kids—unfathomably rich. Maybe we never were a family. We knew we had never been a family. But maybe the CEO was just in it for the money. No, my teammates said—power. Power seemed right
; we could agree on power.

  We focused on staying hopeful. We reassured ourselves that this was just a phase; every startup had its growing pains. The problem, we discussed between drags on cigarettes, was that we did care. We cared too much. We cared about one another. We even cared about the CEO, who made us feel like shit. We wanted a good life for him, just like we wanted good lives for ourselves: we hoped he would get the chance to experience his own messy, reckless, ambivalent twenties. We didn’t acknowledge that he might not want that for himself—he wasn’t like us, didn’t envy us, didn’t care.

  Eventually we were drunk enough to change the subject, to remember our more private selves: the people we were on weekends, the people we had been for years. We talked about where we’d once imagined ourselves at this stage. More stable, less anxious. More in control. We wanted power, too.

  We threw our dead cigarettes on the sidewalk and ground them out under our toes. Phones were opened and contract drivers summoned; we gulped the dregs of our beers as cartoon cars approached onscreen. We dispersed, off to terrorize sleeping roommates and lovers, to answer just one, two more emails before bed.

  Eight hours later, we were back in the office, slurping down coffee, running out for congealed breakfast sandwiches. Tweaking mediocre scripts and writing halfhearted emails, throwing weary and knowing glances across the table.

  Being the only woman on a nontechnical team, providing customer support to software developers, was like immersion therapy for internalized misogyny. I liked men—I had a brother. I had a boyfriend. But men were everywhere: the customers, my teammates, my boss, his boss. I was always fixing things for them, tiptoeing around their vanities, cheering them up. Affirming, dodging, confiding, collaborating. Advocating for their career advancement; ordering them pizza. My job had placed me, a self-identified feminist, in a position of ceaseless, professionalized deference to the male ego.

  From time to time, the women in the office would go out to a nearby wine bar with fake fireplaces and plates of sweating charcuterie, and try to drink it out. I enjoyed these outings, even if they bore the metallic taste of duty—less a support network than a mutual acknowledgment. The other women were smart, ambitious, and a little quirky. One, a new account manager, worked on a treadmill desk and led a daily series of midafternoon crunches and push-ups to combat enervation and get our endorphins flowing. She was also a poet, I learned, which excited me. We should have gotten along better than we did, but it seemed impossible to bring our outside interests into work: they felt out of place and a little sad, like an outfit that looks put-together and chic at the beginning of the day but preposterous and overreaching by dusk.

  I often wondered what work was like for our communications director, who was in her mid-thirties and had come through the investors. She was vastly more experienced than anyone else at the company, and far too professional to gossip or complain. She left the office every day at 5:00 to pick up her kids, and I suspected she was penalized for this: marketing and communications did not grow with the rest of the startup. There was no one else on the team. The CEO kept a drawing of himself, made by one of her children, pinned to a corkboard next to his workstation.

  Other women I knew who worked in male-dominated offices all had unique coping strategies. Some took it as an opportunity to educate and course-correct. Some liked to scare and shame their colleagues for unabashed sexism. Others enjoyed the power play of workplace flirtation. One friend told me she regularly made fun of her CEO for having a gigantic dick, which she had discovered after sleeping with him. “Just inhabit your sexual power,” she advised. “And use it to fuck with them.”

  If I had any sexual power, I didn’t want to inhabit it in the office. I just wanted to keep up. There was one small exception: whenever we went out drinking, the account manager would, without fail, turn to me at the end of the night and ask me to slap him across the face. I knew it probably carried some sexual gratification for him, but I didn’t care—it was very cathartic. It wasn’t like he was asking me to spit in his mouth.

  I wanted the men on my team to think I was smart and in control, and to never imagine me naked. I wanted them to see me as an equal—I cared less about being accepted by men sexually than I did about being accepted, full stop. I wanted to avoid, at all costs, being the feminist killjoy.

  * * *

  The Engineering team recruited a back-end developer straight out of a top undergraduate program: our first female engineer. She walked confidently into the office on her first day, springy and enthusiastic, carrying a leather purse that was not large enough to hold a laptop. I admired this: setting expectations by accessory.

  The engineer’s onboarding buddy brought her around to make introductions. As they approached our corner, the account manager leaned over and cupped his hand around my ear: as though we were colluding, as though we were five years old. “I feel sorry,” he said, his breath moist against my neck. “Everyone’s going to hit on her.”

  * * *

  I was the feminist killjoy. I did not pick my battles. I died on every available hill. I asked my coworkers to stop using words like “bitch” in the company chat room. I bitched about being one of six women at a company of fifty. I wondered aloud if perhaps it was inappropriate to converse in graphic detail about app-enabled threesomes in the open-plan office. I stopped wearing dresses, to stanch a recruiter’s stream of strange and unsettling compliments about my legs, which he spoke about as if I were a piece of furniture. A chair without a brain. A table with shapely legs.

  Sexism, misogyny, and objectification did not define the workplace—but they were everywhere. Like wallpaper, like air.

  The Account Management team brought on a man who spoke in inscrutable jargon and maintained a robust fleet of social media accounts; he had thousands of followers, and behaved as if he were an influencer. He was constantly changing his job title on a website where people voluntarily posted their own résumés, giving himself promotions to positions that did not exist. He told us, with some reluctance, that he was in his early forties. Age discrimination was crazy in this industry, he said. Local cosmetic surgeons were making a mint.

  The influencer brought a scooter into the office and rolled around barking into a wireless headset about growth hacking: value prop, first-mover advantage, proactive technology, parallelization. Leading-edge solutions. Holy grail. It was garbage language to my ears, but customers loved him. I couldn’t believe that it worked.

  One afternoon, he rolled up to my desk. “I love dating Jewish women,” he said. “You’re so sensual.” How did he know I was Jewish, I wondered, but of course he knew I was Jewish: large aquiline nose, gigantic cartoon eyeballs, eyelashes long enough to smash against the lenses of my glasses. I had the zaftig figure and ample rack characteristic of my sensual Ashkenazi kin. What did he want me to say, I wondered—thanks? Jewish people really value education, I mumbled.

  I brought the comment up to the solutions manager during one of our perambulating one-on-one check-ins. I wasn’t trying to get anyone in trouble, I said, as we walked past a sandwich shop effusing artificial bread scent, and the comment was not in and of itself so offensive—but I had to think about the influencer’s sexual proclivities in the middle of my workday, and I wanted not to do that.

  I felt guilty even mentioning it: the solutions manager didn’t want to think about his team members’ sexual proclivities either. We turned in to a corporate park with a brutalist fountain. I had a brief fantasy about lowering myself into the basin and floating away. I remembered the conversation we’d had in which he had told me the company wanted to keep me, and my horrifying response: Thank you, I’d said. I’d like to be kept. I remembered his criticism, that I was a pleaser. I wanted to be less of one. I did not know how.

  The solutions manager seemed embarrassed. “I’m sorry that happened,” he said, staring at the sidewalk. “But you know him. That’s just who he is.”

  At Christmas, the analytics startup rented out the newspaper-t
hemed bar around the corner. The party was called for 4:00 p.m.; we carried our dress clothes into work and cleaned up in the office bathroom, like middle-school students preparing for a dance in the gymnasium. We were excited and exhausted, ready to celebrate.

  I had already discussed with some of the women just how inappropriate was appropriate, and while others had dressed normally, I went conservative. I wore a black collared dress, black tights, and black boots, feeling vaguely like I was in an offensive Halloween costume: sexy Mennonite; naughty Lubavitcher. One of the newer account managers, taking pity on me, shellacked my hair into ringlets. I watched in the mirror as she traced halos of hair spray around my head.

  It was disorienting to see my colleagues in formal wear. I had met most of my coworkers’ significant others, but some were a mystery. I was delighted to see the exercise-fanatic account manager curled into the arm of a man wearing barefoot sneakers with articulated toes.

  Cocktails in hand, the CEO and technical cofounder stood onstage, between parted velvet curtains, and gave a speech about how far we’d come. “A special thank-you,” they said, extending their glasses, “to the partners and spouses.” The partners and spouses, who had left their own jobs early to attend, clapped politely and chastely kissed the cheeks of their counterparts. I was glad that Ian was running late.

  We traveled to a Michelin-starred restaurant, which the startup had also bought out for the night. Silent and dark-suited waiters served us Dungeness crab and seared black sea bass, Wagyu beef and lobster potpie, bottles of wine. The bar was open. People made out with their dates in a photo booth, unaware that it was digital—the photos would all be sent to the operations manager the next morning. Energy shots and lines of cocaine materialized in the bathroom. We danced against the glass windows of the restaurant—napkins strewn on the tables, shoes torn off—avoiding eye contact with the waitstaff.