Why you should care

Chief operating officer Jen Wong is turning the internet’s front page into a space where advertisers want to be. 

“No one gives a shit if you were sexually assaulted because you idiots deserve it for wearing slutty clothes!” a Reddit user wrote in 2017 to an unidentified group of women he saw jogging in yoga pants that morning. The comment was posted in the subreddit r/incels, a group of men who gained notoriety for claiming to be “involuntarily celibate,” blaming women and society at large for their unsuccessful sexual pursuits.

Today, r/incels is banned from Reddit, along with subreddits like r/Nazi, r/farright and many other groups spewing racism, sexism or hate. The move was part of a larger evolution for “the front page of the internet” in 2018 that included redesigning the website, growing its team to nearly 500 employees and substantially increasing ad revenue. But enticing advertisers to spend money on a platform that calls to mind hate speech is no easy task.

That’s where Jen Wong comes in.

A self-described “die-hard New Yorker,” Wong joined Reddit as chief operating officer last April as the company accelerated its courtship of advertisers and partners. Over the past three years, Reddit says it has grown its revenue by five times — though the private company won’t reveal exact figures. Wong says Reddit — which has toyed with going public — will one day bring in as much money as Twitter ($758 million in Q3) or Snap ($298 million).

All platforms have unique challenges when dealing with hate speech.

Jen Wong

Wong, 42, was previously the global head of business operations at AOL, where she oversaw acquisitions like the Huffington Post and TechCrunch, and was the chief business officer at PopSugar. She then became president of Time Inc. and was quickly promoted to chief operating officer by then Time CEO Rich Battista. “She’s whip-smart and incredibly bright,” Battista says. “I needed my No. 2 to be someone I could trust, and I knew she could do the job.” About nine months after Wong joined the magazine, Time broke the top 10 for largest digital audience in the U.S. Prioritizing video growth, she ended up getting the company to 1 billion video views per month.

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Time Inc.’s former President of Digital Jen Wong, now COO at Reddit, poses for a portrait at Reddit headquarters on Friday, Feb. 1, 2019 at the Condé Nast building in New York City.

Source Antonella Crescimbeni/OZY

Social science research has shown that when women are brought in to help turn things around at an organization, they often bear the blame if it doesn’t go well — a theory that’s been coined the “glass cliff.” Wong saw Time through a pretty big evolution and is doing the same at Reddit, but she doesn’t think the theory holds true for her personally. For Reddit in particular, “a lot of the base work had been done when I joined,” she says.

A high-powered media career wasn’t always her obvious path. Although she was a big music and pop culture fan, she decided to major in mathematics as an undergrad at Yale. Growing up on Long Island with Chinese immigrant parents, Wong felt pressure to choose a practical career. “I wanted to be a music producer,” she says, “but that’s not what immigrant parents want their kids to do.”

Still, she was fascinated by music and the internet at an early age. While at Yale in the mid-1990s, Wong decided to design her own blog. More than the coding itself, Wong loved the feeling of community she had online. “But it never occurred to me I could do this for a living,” she says. She worked in finance for a while and got a management science degree at Stanford. But as digital media started to take off, Wong got an MBA from Harvard and set off on a career in the field.

By spring 2018, Wong had taken a Time Inc. buyout and was on a career break to spend time with her son. After she spent years lurking on Reddit and posting only occasionally, the company came calling with an intriguing opportunity. Currently, Reddit is the fifth-most-popular website in the U.S., ahead of Twitter and Instagram, according to Amazon’s Alexa rankings. “It makes you wonder: What is the role of community?” Wong asks.

Rather than simply making Reddit more advertiser-friendly, Wong matches brands with communities that fit their lifestyle and identity. “It’s about finding your people and engaging with them,” Wong says of Reddit’s native advertising strategy.

And how do Redditors feel about the shift? “It’s not that Redditors don’t like ads,” Wong says, “they just don’t like being talked at — you have to invite them into the conversation.” Of course, ads will always be a nuisance to some. Shortly after the redesign in early 2018, user complaints started to pile up, including one who wrote: “I keep getting a recurring ad about diamond engagement rings?? I have literally never looked for an engagement ring in my life.”

A far bigger challenge is how to attract brands to a platform where open racism isn’t necessarily against the rules. Though Reddit has banned some hate-filled subreddits, when CEO Steve Huffman was asked in a Q&A on the site last year whether “obvious open racism, including slurs” is against the rules, he replied: “It’s not.” Reddit leaves it up to the individual communities to decide their own rules. On r/The_Donald there are racist comments posted daily, and r/CringeAnarchy is largely dedicated to transphobic rhetoric, although it is “quarantined,” meaning a warning appears as you click on it: “Are you sure you want to view this community? It is dedicated to shocking or highly offensive content.”

Wong is confident this won’t keep advertisers away. “All platforms have unique challenges when dealing with hate speech,” she says. “But when you post on Reddit, your community has to approve the comment first,” meaning posts must be verified by an actual human being every time — unlike other social media platforms.

And the site’s ad model does have potential, given its huge traffic and niche subreddits allowing brands to connect with their target audience, says Harikesh Nair, professor of marketing at Stanford. But, he cautions, Reddit “will have to carefully balance their monetization [efforts] so as not to anger their users.”

Reddit has also begun growing a direct-to-consumer business with Reddit Coins — a digital currency to show appreciation for a post — and a $5.99 per month ad-free Reddit Premium service.

Wong describes herself as a very goal-oriented person and says she’d love to run a public company one day, though she still makes time to attend reunion tours for favorite bands like the Pixies and Pavement. Wong also spends time with her 17-month-old son, whom she noticed has become quite obsessed with the family’s voice assistant device. “I really hope he asks me more questions than the voice assistant,” she laughs.

A real-life “Ask Me Anything” session, coming soon.

OZY’s 5 Questions With Jen Wong

  • What’s the last book you read? How to Talk So Kids Will Listen … & Listen So Kids Will Talk.
  • What worries you? How immediate everything will be for younger generations.
  • What is on your bucket list? To go to Ethiopia.
  • Who is your hero? Mr. Rogers.
  • What’s one thing you can’t live without? Music.

Read more: How was your day … internet troll?

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