By the end of her sophomore year at Princeton, Alexandra Cerf had thousands of condoms underneath her bed. As a brand ambassador for Billy Boy—a European condom manufacturer—she received 350 condoms a month, which she was expected to distribute to students across campus. Ideally, her employers explained to her, she should find clever and unexpected ways to go about this.  Ambassadors at other schools would leave boxes of condoms on the doorsteps of fraternity houses, or decorate public statues with them late at night. The goal was “guerrilla marketing”— witty and memorable gimmicks that would make Billy Boy a topic of campus conversation.

But Cerf was anxious about making a spectacle of herself. She handed the condoms out to her friends, but for the most part, they piled up in boxes in her dorm room, along with T-shirts, sunglasses, beer koozies, temporary tattoos, ping pong balls, and other company swag, all branded with the Billy Boy logo: a grinning, erect penis.

According to the marketing blog Social Horsepower, a brand ambassador is an individual who “embodies the brand he or she is endorsing.” As human representatives of a brand’s aesthetic or lifestyle, ambassadors “provide credible, trustworthy promotion or visibility” for a company or product. These jobs aren’t limited to college students—Lululemon, for example, enlists a handful of yoga teachers, fitness coaches, and career triathletes to help promote each store location. But given the insular nature of college communities, many companies specifically hire “campus representatives” to help them reach an undergraduate audience.

Princeton’s notoriously self-contained world has hardly slipped under the corporate radar. Over the past decade, brands including Vineyard Vines and Next Step Realty have begun employing Princeton students to make their companies familiar names on campus. When I first heard about these positions, I was intrigued by their open-endedness. What, after all, did it mean for a human being to embody a company? Envisioning catalogue-ready outfits and brand-name tattoos, I set out to expose Princeton’s undercover marketing agents, hoping to draw some ambitious conclusion about corporations subsuming individual identity.

Instead, I found, what brand ambassadors actually do varies as much as the kinds of companies they represent. For some, the job requires little more effort than posting a handful of photos to Instagram each month. For others, like Cerf, expectations were much more intense. Nearly all the students I spoke to, however, faced pressure to tap their own social networks—sororities, sports teams, and eating clubs—to help their brands gain visibility and, ultimately, turn a profit.

As people grow increasingly conscious of marketing ploys, many business writers have pushed ambassador programs as the solution. While traditional ads are easy to dismiss as gimmicks, brand ambassadors are tougher to distrust, if only because we don’t encounter them in a commercial context. One 2013 article in Forbes Magazine summed this up by noting that, in today’s society, “companies don’t have much social capital, but people do.” By attaching a face and voice to consumer goods, the thinking goes, companies can make initially unpopular products familiar and desirable.

The whole appeal of brand ambassadors, it seems, rests on their perceived honesty: advertisements lie, real people are trustworthy. According to Forbes, this is the reason word-of-mouth promotion is so successful. And when this promotion is, in fact, as honest as it is meant to appear—when, say, a campus representative is genuinely enthusiastic about his or her brand—this strategy can be effective. But when, as in Cerf’s case, the goals of the brand don’t align with the goals of the student representing it, the job becomes much more difficult.

Cerf graduated from Princeton in 2015, so I called her on the phone. When I explained my project to her, she laughed. “I was probably the worst brand ambassador that ever existed,” she told me. As she re-hashed her experience, she kept emphasizing its bizarreness, noting that this was not something she’d ever put on her resume. At one point, she explained that her boyfriend, who was in the room with her, had never heard about this period of her life—it was all new for him, too. Whatever antics she might have gotten up to as a college condom rep, it was clear she had moved on.

Cerf explained that she’d begun working for Billy Boy her sophomore year, after her friend, a Billy Boy ambassador at Columbia, Facebook messaged her about the opportunity. Her friend was enthusiastic, and pay was competitive: the position offered $250 a month, which in retrospect Cerf calls “disgustingly absurd.” After a casual interview—“they basically just had me prove that I was social,” she told me—she was offered the position. She believes she was the only person from Princeton who applied.

As soon as the company swag began arriving, Cerf began to question her decision. “I was like, no one is going to wear these things or want them, this is insane,” she said of the apparel. She jokingly offered it to her friends—who, she said, found her job “hilarious”—but was too inhibited to give it away publicly. She was more open with the shipments of condoms: as an RCA, she was required to provide condoms for her Zee group, and she posted several Facebook statuses offering up her growing supply. Still, she was nowhere near ready to undertake the “guerilla marketing” her employers encouraged her to do.

Many of Cerf’s reservations had to do with how she felt other students would see her. Unlike most jobs, which allow us to draw a line between our professional and private selves, being a brand ambassador requires publically equating your personal identity with a branded image. If the two align, this is no problem. But Cerf was anxious about other students seeing her as the hyper-sexual, prank-pulling rep she felt Billy Boy wanted her to be. She had joined Pi Phi her freshman year, and especially feared the judgment of the older girls. “I definitely had some anxiety around, ‘will people think that I’m super strange or uncool for doing this,’” she told me.

Margaret Spencer found herself in a parallel position when she became a brand ambassador for a San Francisco-based startup that ships themed care packages. Spencer is currently taking a gap year to work in New York, and when I called her she was similarly dismissive of her freshman year job. “The more I talk to you, the worse I feel because I’m such a bad case study,” she said. In fact, almost everyone I spoke to seemed convinced her experience was an outlier, somehow not reflective of whatever a brand ambassador is supposed to do or be. Even Hadley Newton, whose tabling for the popcorn company BoomChikaPop prompted the brand to sell out at the U Store and subsequently up their order, prefaced her story by noting that her involvement with the company was “really short and probably not a typical experience.” The fact that so few people were willing to own their promotional work made me wonder what, exactly, a “good,” or “standard” brand ambassador looked like—and if this was even possible.

Spencer blamed her perceived shortcomings on her own lack of commitment, explaining that it was hard to give the position her all when other students were so apathetic towards her efforts. “I was probably a really shitty [brand ambassador], because I immediately realized Princeton students will not pay $40 [for a care package],” she explained. ‘The response that I saw was so tepid that I really didn’t see a point.”

Most of Spencer’s job revolved around promoting the brand on social media, specifically Instagram. She would take pictures of products and run contests, not explicitly marketing so much as helping the company to curate a compelling online presence. She ran only one giveaway, after her boss shipped her several hundred company buttons. “They were actually kind of cool, so I handed them out at Frist,” she said, adding dismissively, “I mean, I sat at the table and did work.”

More than simply not caring, though, Spencer felt her promotional efforts were out of place at Princeton. “I feel like there’s something about Princeton being so subdued in a way, like even if you’re publicizing something, it’s done in a very controlled manner,” she said. “I think anything that’s not the norm is questioned kind of violently, and this, especially, seemed to not have a place.” After a year, Spencer and her employer mutually decided to cut her position.

Like Spencer, Cerf felt her position stood in direct conflict with campus culture. At a school where giving out promotional pins is seen as a transgression of social codes, giving out penis t-shirts, she felt, was asking to be talked about. Of course, gossip was precisely what Billy Boy wanted. But Cerf wasn’t willing to give up her own social comfort in order to make money. “No way am I going to ruin my reputation for anyone who I don’t actually already know,” she said.

Beyond her own inhibitions, Cerf sensed a mismatch between what the company expected of Princeton students, and what students were willing to accept. “People at Princeton are very hyper-aware of their reputations and don’t want to have a picture taken with a penis on their shirt that can resurface in 10 or 20 years when they’re running for office,” she explained. Even had she put more time and effort into marketing Billy Boy, she doesn’t believe students would have bought in.

For Liz Ostertag, the challenge was not so much overcoming students’ apathy or resistance as coming to terms with the fact that her brand was fundamentally flawed. A senior, Ostertag is tall, blonde, and athletic, and she spoke guardedly, careful to stress how much she had gained from the experience. As we kept talking, however, it became clear that Ostertag had faced a unique dilemma: how can you be a trustworthy advocate for a brand you don’t trust?

Shortly after she began working for Smacktive—an iPhone app she describes as “Tinder for sports”—Ostertag realized that it had significant safety issues. Like Tinder, Smacktive connected users with a stranger, but based on athletic rather than romantic interest. Instead of dating, for example, users can plan a run, or a game of pickup basketball. Initially, Ostertag thought this was a strong idea—a runner herself, she liked the idea of always having a workout buddy. But Smacktive did not ensure that the stranger it connected you with was a real person, and did little to safeguard users against sexual predators.

When students called her attention to these flaws, Ostertag understood. “Especially as a girl, I realized [safety] is a really important thing,” she said. She found the app increasingly difficult to promote. “I didn’t feel like I could go up to friends and say ‘use this app, I’m sure it’s safe,’ because I couldn’t really say that,” she said. While she suggested changes—such as an option to see mutual friends—students remained unconvinced of its security, and by the following fall Smacktive had given up on its brand ambassador program at Princeton.

As she described the promotional events she had scheduled—a Chipotle study break, a spin class at Dillon— it became clear that Ostertag had cared deeply about the company. But as much as she wanted to succeed as an ambassador, she could not justify promoting a product she felt to be so deeply flawed. Unlike Cerf and Spencer, whose discomfort was primarily social, Ostertag felt continuing to market Smacktive meant crossing moral lines. She knew that other students trusted her, and she couldn’t bring herself to put her peers in danger for a profit.

The only student I spoke to who didn’t seem to have faced any challenges was Devon Naftzger, a senior who represented customizable group-buy clothing company The Social Life. I met Naftzger in Starbucks, where she usually spends her afternoons doing schoolwork. She was wearing a puffy, lime-green vest and had her sorority’s letters flash-tattooed on her hand. “It was just something that was easy,” she said of her job. “Not even five minutes to make a couple bucks.”

Naftzger explained that she had applied for the position the summer after her sophomore year, when she bought a shirt through her sorority sisters and noticed a recruitment link at the bottom of the receipt email. “They asked for my resume and stuff, but really they just wanted someone who was connected to groups on campus and comfortable reaching out,” she said of the application process. This was no challenge for Devon, who eagerly scheduled meetings with the heads of eating clubs, other sororities, and the club soccer team.

Given that matching gear is a must-have for practically every student organization at Princeton, Naftzger faced none of Cerf’s anxieties about embarrassing herself. Nor did she worry about marketing a faulty product—after all, she had purchased gear from The Social Life herself. With a market already in place, Naftzger’s job was simple: network. She was a natural.

Cerf didn’t lack social connections. But instead of selling something that is already an established part of campus culture, she was giving away accessories that violated just about every unwritten rule about subtlety at Princeton. In this sense, precisely what qualified Cerf to be a brand ambassador—her social status—was what made actually carrying out the position impossible. For a while, she did the bare minimum, exaggerating her efforts in mandatory monthly reports to the company. “I wasn’t really lying, but I would do something and exaggerate how many people had seen it,” she said, such as: “’I did this for the whole college instead of just my dorm,’ or giving [condoms] to this entire frat when I was giving them to the people in my grade in that frat who I knew.”

She carried out one of her most memorable “hacks”—as the company called these promotional pranks—in December, when Billy Boy mailed her holiday goodie bags containing an assortment of candy along with a condom. Cerf dropped them off outside every door in her dormitory, feeling she was, for once, actually fulfilling her employer’s expectations. But when, midway through her sophomore year, the company began requiring photographic evidence of hacks, Cerf knew she could not keep the job for much longer. In February, she was fired.

If being a successful brand ambassador actually means embodying a brand—surrendering one’s own identity to become a walking, talking billboard for a product—few, if any, of these students achieved this. Because of social pressure, or ethical dilemmas, or sheer lack of interest, some aspect of these students’ human selves got in the way. And as I listened to their stories, I found myself wondering if the whole idea that a human being could represent a company wasn’t somewhat unrealistic. If we trust brand ambassadors more than advertisements, we trust them for a reason. Unlike ads, people can see and respond to product flaws; they can empathize with concerned consumers. They have their own values and priorities—and those priorities are not necessarily always in line with making a profit.

The last week of Cerf’s sophomore year, her friend’s quad threw a party. Eager to get rid of her boxes of Billy Boy swag, she decided to bring it along as a joke. “I couldn’t give it all away,” she explained. “The party just became everything with this logo on it…it was pretty hilarious.” The condoms, however, were harder to leave behind. A year after graduation, the boxes are still in her parents’ attic, by now more than likely expired. At some point, she said, she’ll dispose of them for good. In the mean time, they’ll remain in their branded packages, collecting dust.

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