Uncanny Valley

by Anna Wiener

  Churn was customer drop-off: when a customer realized they didn’t need a third-party product, or forgot to use the tool, or switched to a competitor. Getting bigger was both a blessing and a curse, in this respect. It meant that we were gaining, but it also meant that newer startups had us in their sights. Competitors were coming on the market—smaller, nimbler companies with fewer employees and fresher funding. They were able to offer pricing that we, as a slightly more bloated company, were reluctant to match. They had a higher tolerance for burn.

  But churn wasn’t just about pricing or shifting loyalties. As with any business-to-business product, it often arose from neglect, when companies were paying thousands of dollars every month for a tool they forgot could be helpful. This was always the most damning feedback, because it meant that we had been forgotten.

  I would meet accounts at their offices—NDA at reception, snacks and flavored water in the conference room, views of the bay from the Engineering cluster—and they would explain, matter-of-factly, that they were paying too much for something their engineers could just build themselves. It wouldn’t be as pretty, but they could roll their own—pull their own solution together. The online superstore had begun selling back-end infrastructure that made this especially easy. Ours was a great tool, our customers said, but they needed to get the cost down.

  I had trouble arguing with people who needed to downsize, but I didn’t mind going on-site to try. It always felt like a field trip. I went to well-established corporations and admired the casual, carefree air of people who only put in three hours of work a day. I went to startups and declined offers of iced tea and string cheese. I brought the linen blazer back out. I thought I had such authority.

  I didn’t know that customer success managers at other companies were usually young women who somehow didn’t look dowdy in floral prints and never left the house with wet hair, whose socks always matched, who didn’t make too many jokes, who always knew the answers. Women who were much better at the job than I was—far more persuasive. Women to whom saying no was impossible.

  It was easy to say no to me. I was always picking lint off my own chest, trying to skate by on good humor. When I met with customers, I acted like I was cosplaying a 1980s business manager. I said things like, Tell me what you want from your data, and Let’s define your North Star metric. The North Star metric was always the same: whatever brought in money—as much of that as possible. I sat in conference rooms and reclined in comfortable chairs and tried to cultivate an aura of expertise. It was unclear whose mannerisms I had assumed, what fantasy I was channeling.

  Though I knew I was unconvincing, the performance still seemed to work. It was reassuring to remember that the jobs we all had were fabrications of the twenty-first century. The functions might have been generic—client management, sales, programming—but the context was new. I sat across from engineers and product managers and CTOs, and thought: We’re all just reading from someone else’s script.

  I skimmed recruiter emails and job listings like horoscopes, skidding down to the perks: competitive salary, dental and vision, 401(k), free gym membership, catered lunch, bike storage, ski trips to Tahoe, off-sites to Napa, summits in Vegas, beer on tap, craft beer on tap, kombucha on tap, wine tastings, Whiskey Wednesdays, Open Bar Fridays, massage on-site, yoga on-site, pool table, Ping-Pong table, Ping-Pong robot, ball pit, game night, movie night, go-karts, zip line. Job listings were an excellent place to get sprayed with HR’s idea of fun and a twenty-three-year-old’s idea of work-life balance. Sometimes I forgot I wasn’t applying to summer camp. Customized setup: design your ultimate workstation with the latest hardware. Change the world around you. We work hard, we laugh hard, we give great high fives. We’re not just another social web app. We’re not just another project-management tool. We’re not just another delivery service.

  I got a haircut. I took personal time. I shrugged off the salespeople’s knowing looks whenever I came into the office wearing anything dressier than a T-shirt and jeans.

  I knew, from visiting my accounts, that startup offices tended to look the same—faux-midcentury-modern furniture, brick walls, snack bar, bar cart. When tech products were projected into the physical world they became aesthetics unto themselves, as if to insist on their own reality: the office belonging to the home-sharing website was decorated like rooms in its customers’ pool houses and pieds-à-terre; the foyer of a hotel-booking startup had a concierge desk replete with bell (but no concierge); the headquarters of a ride-sharing app gleamed in the same colors as the app itself, down to the sleek elevator bank. A book-related startup held a small, sad library, the shelves half-empty, paperbacks and programming manuals sloping against one another. It reminded me of the people who dressed like Michael Jackson to attend Michael Jackson’s funeral.

  But one office, of the blogging platform with no revenue model, was particularly sexy. This was something that an office shouldn’t have been, and it jerked my heart rate way, way up. There were views of the city in every direction, fat leather love seats, electric guitars plugged in to amps, teak credenzas with white hardware. It looked like the loft apartment of the famous musician boyfriend I thought I’d have at twenty-two but somehow never met. Being in the space made me want to take off my dress and my shoes and lie on the voluminous sheepskin rug and eat fistfuls of MDMA, curl my naked body into the vintage ball chair, never leave.

  It wasn’t clear whether I was there for lunch or an interview, which was normal. I was prepared for both and dressed for neither. My guide led me through the communal kitchen, which had the trappings of every other startup pantry: plastic bins of trail mix and cheese crackers, bowls of chips and miniature candy bars. There was the requisite wholesale box of assorted energy bars, and in the fridge were bottles of flavored water, string cheese, and single-serving cartons of chocolate milk. It was hard to tell whether the company was training for a marathon or having an after-school snack. But it wasn’t unfamiliar—just a few days prior, I had walked into the analytics startup’s kitchen to find two account managers pounding chewy cubes of glucose marketed to endurance athletes.

  Over catered Afghan food, I met the team, including a billionaire who had made his fortune from the microblogging platform. He asked where I worked, and I told him.

  “I know that company,” he said, tearing a piece of lavash in two. “I think I tried to buy you.”

  * * *

  Courtside seats to other startups’ volatile trajectories had made me jaded, picky. Not that picky—I just wanted to work for a company that was innovative, rather than opportunistic, with a stable revenue model and a mission I could get behind. Maybe another pickax, but a normal business would be fine. Something useful. Somewhere I could take a breath, take stock.

  A friend worked for a startup that made tools for developers—software for software engineers, to help them build more software—and she spoke highly of the work-life balance. The company was famous: everyone, from Silicon Valley’s office park incumbents to the United States government, used its products, which made it simple for programmers to store, track, and collaborate on source code. The company also operated a public platform with millions of open-source software projects, which anyone could contribute to or download for free. Excitable tech journalists sometimes referred to this platform as the Library of Alexandria, but for code.

  “I’m not trying to poach you, but it seems obvious to me you would be a great fit,” my friend told me over lunch, while extolling the virtues of her employer: two hundred employees, no real competitors, a hundred million dollars in funding. She dipped a french fry into her milkshake. “If you wanted to run a team, that’s something that could happen. You could try it on, see what works for you.” It all sounded so relaxed.

  Things had not ended well for the Library of Alexandria, but I was still intrigued. The company had a real business model—selling private and self-hosted versions of the platform to corporations that wanted to apply the collaborative, open-source approach
to proprietary software—and the public, free website struck me as radical. It offered unfettered access to the tools, knowledge, and online communities of the elite: a defensible allocation of venture capital. The startup glittered with idealism and old-school techno-utopianism. It was a corner of the industry that I found optimistic, experimental, and, most important, redemptive of the whole enterprise. I could see how it might actually make the world a better place.

  There was, of course, a red flag. That spring, the startup had been implicated in a highly publicized gender discrimination scandal. The first woman on the engineering team—a developer and designer, a woman of color, and an advocate for diversity in tech—had posted a series of grievances to the microblogging platform. The startup, she claimed, was a boys’ club, a sexist institution, down to the core: colleagues condescended to her, reverted and erased her code, and created a hostile work environment. She described a company culture where women were disrespected and intimidated.

  The developer’s posts went viral. The story wound its way up into the national media. The startup conducted an investigation. An implicated founder stepped down, and another moved to France. The venture capitalist who claimed software was eating the world took to social media to pledge his allegiance to the company.

  All of this made me leery, but I also wondered, privately, if there might be some benefit to joining an organization immediately after this sort of blowup. I did not anticipate a matriarchal feminist utopia—based on the company’s team page, about 20 percent of the employees were women—but I pictured a standard-issue boys’ club deteriorating under the corrosive effects of chatter and public scrutiny. At the very least, I figured, employees would be talking about sexism openly. Sexism had to be part of the internal conversation. I’d read Foucault, a million years ago: discourse was probably still power. Surely, in the fallout, women would have a place at the table.

  Call it self-delusion or naïveté; I considered these calculations strategic.

  * * *

  I took a personal day without giving a reason, an act of defiance that I feared was transparent, and scheduled an afternoon of interviews at the open-source startup. The office was a three-story former dried-fruit factory by the ballpark. In the reception area was a collection of glass museum cases showcasing artifacts from the company’s history. I peered at a dented laptop that had belonged to one of the company’s first engineers, and tried to feel moved. A security guard wearing a shirt with the company logo and the words SECRET SERVICE showed me to the waiting room and gestured toward a yellow couch. I took a seat, smoothed my hands over my lap, looked around, and dissociated.

  The waiting room was a meticulous replica of the Oval Office, down to the wallpaper. The rug, a deep presidential blue, was emblazoned with the startup’s cartoon mascot, an imaginary animal—a tentacled, doe-eyed octopus-cat crossbreed—holding an olive branch above the words IN COLLABORATION WE TRUST. An American flag stood to the side of the Resolute desk, behind which played an animation of clouds passing over the National Mall. White doors with precise, triangular molding led, presumably, to the West Wing.

  This was peak venture capital, the other side of the ecosystem. The company appeared to be spending its hundred million dollars in venture funding the way any reasonable person would expect founders in their twenties to spend someone else’s money: lavishly.

  I didn’t need to compare the office to the austere, fluorescent-lit tundra of the analytics startup, or even to Ian’s cool, industrial-chic robotics warehouse, to appreciate the novelty of the work space. It was a fever dream, a fantasy, a playground. It was embarrassing, too giddy; more than a little much. When I entered a glass-walled, intimidating simulacrum of the White House Situation Room for my first interview, and saw that the boardroom table was flanked by two flags printed with the words IN MERITOCRACY WE TRUST, I laughed out loud. At each seat was a leatherette table pad embossed with the octopus-cat. It was all so literal.

  Most surprising was that I liked it. The decadence excited me. What else happened here, I wondered—what else might employees get away with?

  After months of being DFTC without once hearing the word “overtime,” I was also thrilled by how the company appeared to rank on the ass-in-chair metric. By six in the evening, in the middle of the workweek, the office was dead quiet. With the exception of a half dozen employees pulling themselves beers and shaking cocktails at the bar, it was almost entirely empty.

  I had the premonition that I would never again work in a startup office that looked like it could be disassembled overnight, or in a culture-industry suite with mismatched coffee cups and drafty windows. I would not wear stretch-rayon business casual. I would not see mice. I would become self-actualized by achieving a healthy work-life balance, and I would allow myself to be taken care of, as if I had done something to deserve it.

  If this was the future of work, I thought, then I was all in. I wanted every workplace to be like this—I wanted it for everyone. I believed that it was sustainable. I believed that it would last.

  * * *

  “We’re expecting big things from you, ourselves, and for the company,” read the offer letter, with condescension I found only vaguely objectionable. “You should be justifiably proud.” I was, and I wasn’t. Mostly, I was burned out.

  The job offered top-of-the-line, fully covered insurance, partial 401(k) matching, and unlimited vacation, but it would entail a ten-thousand-dollar pay cut and a title demotion. For the time being, I wouldn’t even be moving laterally; taking a typical customer support role was climbing down the ladder. This was an ill-advised move in any professional context, and especially naïve in the tech world: as an early employee of a promising startup, I could be leaving potentially high-value stock options on the table. But I didn’t have stock options worth worrying about, and I didn’t care about a huge payout, or titular glory—which was good, because the job title listed in the offer letter was, in homage to the company mascot, Supportocat. I set that humiliation aside.

  What I wanted in a workplace was simple. I wanted to trust my manager. To receive fair and equal compensation. To not feel weirdly bullied by a twenty-five-year-old. To put some faith in a system—any system would do—for accountability. To take it all much less personally, and not get too close.

  * * *

  I called Parker. “Well, it’s not ad tech,” he said, deliberating. “So, that’s good. And it’s beloved by a lot of nerds. And the deal for working there, for any tech company, is so good right now. They’ll make all the decisions for you. It’s like going to a monastery, but better paid. The trade-off for that is you’re not really encouraged to think about what you’re doing. But you know that. I’m sure you’ve thought about that.”

  I had not really thought about that. But I believed in the mission, I told him. I didn’t see the harm. I confessed that I thought the open-source platform had radical potential. Parker was quiet for a moment.

  “For me, it’s a dark specter of centralization,” he said. “In a world without it, we could still do the things the platform allows, and people would be freer.” He sighed. “But I’d prefer not to shame you, no matter where you go. There almost isn’t a company you can work for that’s good. Maybe a few nonprofits that aren’t actively making things worse, but that’s it. It’s a very short list. Nothing you do is going to be more pernicious than the background radiation of SoMa.”

  I’m just going to take it, I said.

  “Yeah,” he said. “I know.”

  * * *

  I scheduled a meeting to give notice. The solutions manager and I sat down in the Pentagon, and I offered the lines I had been rehearsing in my head: I learned so much, enjoyed my time, was grateful they had taken a chance on me. None of this was a lie. They had taken a chance on me. I had enjoyed my tenure, to a point. It had been an invaluable education.

  The solutions manager leaned back in his chair and nodded. Around and around went the wedding ring. I knew that he had cried when he fired N
oah, and I felt a little disappointed that he wasn’t crying about me. He asked, perfunctorily, if there was anything that the company could do to get me to stay. I told him no, and we both seemed relieved.

  I thought it was most dignified to personally tell the CEO I was leaving, like a protocol he might have read about in our VC’s business book, but the solutions manager beat me to the punch. Throughout the day, I eyed the CEO, and he studiously ignored me. When I approached him, he turned on his heel, walking away while staring into the middle distance.

  That evening, from the blissful isolation of one of the conference rooms, I saw the CEO striding across the office in my direction. Still avoiding eye contact, he entered the conference room, sat down, and told me he had heard my news. News: like I was pregnant, or dying, or important. I nodded and tried not to apologize. Like a high school drama student running lines, he thanked me for my work. “I’m sorry I made you cry that one time,” he said to the window behind me.

  I had not gotten to know him, I thought. We were not friends. We were never family. I did not understand the sacrifices he had made for the company, or how far he would go to protect it. I did not know what made him tick. There was a coldness that frightened me.

  I reassured him that it was fine. This was a lie, but not for his benefit. I needed to believe it much more than he did.

  * * *

  At the end of August, I deleted personal files from my laptop and ate a final handful of trail mix. The operations manager was too overextended to conduct an exit interview, for which I was grateful. I had nothing left to contribute. I said a few overly sentimental farewells and signed more paperwork, none of which I fully understood without a lawyer present. It did not occur to me that I could ask for more time, or even say no.