Reddit's like real life. It's like coming to a dinner party or hanging out with friends. If you showed up in a dinner party and you're like, I'm just going to sell you my new product, you're not going to have a lot of friends.
They're like, I don't want to talk to you. I'm trying to enjoy my dinner right now.
You went to Stanford. I went to Harvard. Sheree went to... you also went to Harvard. Sheree went to Stanford.
It means we're all still paying off debt.
I did not dream of being a business leader. I did not dream of being a technical person. I did not dream of these things. And I often tell people that like it's very hard to sit down and architect your life. Some people do it successfully, but for most people, it's like a journey of discovery and reinvention.
We say you can reinvent yourself at any time.
I like to think that all the time, and that keeps me just excited.
I'm Sheree. I'm Jean. I'm Jen.
And we're the Tiger Sisters.
We are your Wall Street and Silicon Valley big sisters. And we're a top 10 business podcast bringing late night sister talk meets boardroom strategy. When Jen Wong joined Reddit as COO in 2018, it was already one of the most influential corners of the internet. The challenge wasn't building the community, it was building the business. Over the next several years, Jen scaled Reddit from the front page of the internet to a public company. She scaled its advertising business, secured major AI data licensing deals, and helped lead the company through its 2024 IPO. She's had a front row seat to some of the biggest questions shaping the internet today: free speech, community trust, AI, advertising, and what happens when a platform built on authenticity now has shareholders. Today, we are sitting down with Jen at Cannes Lions in Cannes, France to take you on an inside conversation into one of the companies that has consistently shaped culture, conversations, and communities. And it's helped build a global forum for people to feel less alone in this world. Jen, welcome to Tiger Sisters.
Thank you. Thank you. Thank you for having me.
We're so excited to have this conversation. And can we also say hello? We're in Cannes Lions in France.
Guys, if you're not watching this right now, turn on your video and look at this amazing set that we're in. You can't see what we see, but we're in a bubble right now and people can see that we're having this conversation with Jen. It's pretty epic.
Okay, Jen. So, let's go back to 2018 when Reddit was a private company and relatively under the radar compared to its internet company counterparts. You were the COO and president of digital at Time Inc., so you were a pretty big deal. A lot of our audience is in the stage where they're thinking about their next career steps. What was it that convinced you to leave Time Inc. and join as COO of Reddit?
You know, eight years ago, that was a pretty easy decision, but I was not actually on the original call list for the recruitment.
So, I lived in New York and I live in New York. I'm a diehard New Yorker, born and raised. And Reddit was headquartered in San Francisco.
And the search was for a COO who would be in San Francisco obviously. And so I did not get the call actually for that, but they called a friend of mine and he said, 'You know, it's not right for me, but I really think you should call Jen.' And I'm so grateful for that. And with that, I met Steve at the Gordon Biersch at the SFO airport at some ungodly hour as he was passing through and I was passing through and we hit it off and we had more discussions at the office. And I knew it was right for me because when I left Time Inc., there were a couple things. One, I really wanted to go back to pure growth. And even though Reddit was still maybe a little bit of a turnaround plus growth, I think I really saw the opportunity. It's very rare that you have a pillar of the internet with a very large audience that doesn't have a business. It's just like an open canvas, which is amazing. And the second thing was I had at my time at Time Inc. just working in publishing at PopSugar, I'd watched all my editors go onto Reddit and look for ideas. All the editors were constantly looking for social media ideas. What's the next trend? Like kind of mining Reddit already. And I'd watched Reddit grow just on its own without a lot of investment, just growing sort of in the Advanc portfolio. And so I really believed in the opportunity. I had been a longtime user. And even at Time, when Stephen and Alexis came back, I'd reached out and actually just to know, hey, what's going on. So I was really excited, like putting all these things together it just made sense. And I was on the beach because in January we had sold Time Inc. so I was taking time off because I had a newborn at home and I hadn't had time with them. And so I said I was going to take time off maybe six, nine months. And when this opportunity came up, I was like, 'Okay, I'm going to do it.' I'm sort of cutting my break short.
So, you ended up taking how much time off then?
I ended up taking three months off.
Instead of my six to nine. And it was worth it. It was the right opportunity for me. Yeah. Even though I knew I would be on a plane going back and forth and a remote, you know, leader on the team. I think at the time I was the only remote exec.
And what a good friend of yours to offer your name up to be like Jen would be perfect for this role.
Incredible. And that's why I often tell people, yeah, take the phone call from a recruiter and even if it isn't right for you, nominate three great people you know for that opportunity. Like you can spread that to other people and make amazing things happen for people. I always tell people that and I do that today.
That's such a good recommendation. Okay. My question is, so when you joined Reddit in 2018, was there already the plan and sort of like a pathway to going public? And if so, or even if not, like what were the things that you knew had to change to get there?
It's a great question. I think Reddit always being like a pillar of the internet and so different from everyone else and so special. I think Steve and I spoke earlier, we always thought that IPO was the path and that was sort of the context of thinking about the company is to be independent and for Reddit to fulfill its mission independently. So that was the dream I think and there was a lot of work to be done there. We had that idea that that was going to be something that we wanted to do. Yeah. And it made sense for Reddit. But obviously between getting there you really needed, we needed a business and that was less clear what the business would be. There was some advertising at the time. There was also some programmatic advertising. It wasn't all sold by the salesforce. Not clear what the ad products were. And there was also a little subscription business. And so there was a little bit of a debate of like which do you do first? Both are probably really viable on Reddit. Which do you go after first? And you know we decided on ads because ads scales with users and it keeps the platform open and Reddit is, you know, just born of the open internet for people to get information. We didn't want any friction for that. And so I think the ad model really, I mean one, it's a great model when it works. And two, I think was really in line and could be built in harmony with our values and that was really important because I think the digital advertising business has gone through these arcs of really, you know, collecting a lot of first-party data on people for targeting and we of course have anonymous users. So we thought, okay, well, how do we build a great marketing platform that has great outcomes, but doesn't have that apparatus and is different. And so we built this business that's predicated on context. You know, the environment that you're in, you're reading about whatever it is, vegan spices now, like what are you interested, what would be the right ad there. That was based on converting that high intent and high signal that people give on Reddit for their interest into action. And I think that's worked out really well. But we took the bet. You know, advertising platforms are really expensive to build. And so you only do it if you think you're going to be big and therefore can stomach that investment and that build and, you know, we're eight years into this. And we still have a lot more to build. But that was the journey that we decided to take and I think it was one of the best bets that we did.
Quick pause. Here's a productivity hack for you. Outsource your content curation to us. You can count on us to bring you the well-researched ideas, topics, and conversations that people are having. To help us keep making this content, subscribe now wherever you get your podcasts, YouTube, Spotify, or Apple podcasts. And we're launching a Tiger Sisters newsletter coming soon. You can sign up in the link in our description. And now back to the show.
Okay, so this is a little bit in the weeds, but the context is I also used to work in advertising at Snapchat. At Snapchat, I helped build and scale our AR advertising business. So, as you were talking, I was like having all these thoughts. I was like, 'Okay, so building advertising business, but the users are all anonymous.' So, like then how do you like monetize that? But then you're like, 'Oh, it's based on their interest. We know what they're doing because they're writing about it.' So, then that's how you create all the like lookalikes or like affinity sort of targeting, right?
That's exactly right. It's based on your activity on Reddit, the context that the conversation you're sitting in, the communities you spend time with. And it doesn't matter that we don't know your gender, age, etc. Although a lot of that is inferred from... you can probably infer from what you're spending time on, etc., etc. But that's not important. And what is important and what is special about Reddit is that when you are anonymous, you reveal things that you don't reveal when you're under PII, right? So when you're on, when you're under your name, there might be a little bit more posturing. You might be editing who you are and you might not be sharing everything. Do my friends care that I'm an avid gardener? They do not. They really don't. Do they care that I went through this long journey of buying my first car at a very late age? I hadn't bought a car until I was like 40-some, you know, and that was a tough journey for me that I went through on Reddit, but I didn't go through with friends because I was a little embarrassed to do that. So, you reveal things that are more personal to you, which also means you're an incremental customer that somebody can find that you can't find elsewhere.
Yeah, this is like one level deeper because I think the way that I have thought about ads is obviously the demographic information that you have up front, but what I'm hearing you say is that like that's not even as valuable as the niche information that we have on people, maybe their most like vulnerable questions and vulnerable answers that they're getting on Reddit.
Yeah, I think for some things there might be a correlation. For other things I think there is none. You know, if you're going through an illness, a lot of conditions are just a human condition, right? It's not about your gender, etc. And it doesn't matter who you are. It's just a matter of like we're in the same life circumstance. Buying a car is a universal life experience. It doesn't really matter. I mean, in this case, it was pertinent that I was a parent with two kids and I was solving for car seats, but that was pertinent, not my gender.
Yeah, I think this is the secret sauce of Reddit. And also Jean speaking about her experience at Snapchat, I used to work at LinkedIn on the product side and love my time there. I avid LinkedIn but there is posturing and there is a professionalism because your name and identity and work history and resume is tied to what you're putting out there. And so you know there's like a little bit of this going on on LinkedIn. It's very professional. And I would say, and I say this in a loving way, Reddit feels the opposite, you know, in its design, which I think is very clear to me, like the LinkedIn design versus the Reddit design. I think there's something there about how Reddit curates the community where people feel comfortable sharing, obviously with the anonymity that we spoke about, but also something in the design and the forum space where people want to contribute and even if you're not contributing, you feel like you're gaining a lot of value just in the place that you're in.
I think it's architected fundamentally differently. The anonymity I think allows for people to reveal things in a very safe way and I think what makes Reddit different is the structure of communities. So the communities are, you know, they have different objectives. They have different things that they are trying to do and they help the conversation stay on topic and accomplish whatever it is that the community wants. Right? If you're passionate about gardening, lots of different flavors of gardening. There's vegetables, there's flowers, there's, you know, succulents. There's specifically what it is that you are interested in and the people who come to that, I mean you can imagine if you come to a succulent community, you are really passionate about succulents, really deep, trying to make sure that your plants grow, right? And that's your purpose and that's why you're there. You're not there to talk politics or other things that are off topic and neither are the moderators. The moderators are there to have a great conversation about succulents and be helpful on that. And so that makes the quality of the conversation so high. Because everybody's there for a purpose and they're often very knowledgeable about that subject. So in that way it's like self-curating.
I'm laughing because Sheree, I need that Reddit, I need that Reddit thread about succulents because mine will not stay alive.
Sheree's very into gardening and she's a very successful gardener except for succulents.
I think I over... I mean they should be the easiest I think because like they don't have to ignore them. I cannot, I cannot, I overwater them and they die. My jade plant is very sad. All my succulents are very sad. But yes, I need that.
I'm an avid gardener and I've gone through a huge vegetable gardening journey on Reddit. Lots of success and still some consistent failures. I like, carrots will be the death of me.
So that's why it's your go-to example because that's your community.
Yes. I mean I love it and I love the gardening UK community. I think UK gardeners are really another echelon of gardening.
