Joining BuzzFeed

Alex Kracov: You joined BuzzFeed as an intern pretty much right out of college, and I think you're like one of the first 10-ish employees. Can you talk a little bit about what those early days were like at BuzzFeed?

Melissa Rosenthal: Yeah, absolutely. The early days at BuzzFeed were definitely the Wild West. We definitely had a viewpoint and a mission, but the reality is that it wasn't really fully fleshed out on where this would lead us, what it would become. I think it was a bunch of people that just were driven by the idea of disruption and believed that there could be a way to predict virality and understand deeply why people share content. And we were definitely all driven by Jonah, who is the CEO and Founder of BuzzFeed, and really kind of like his whole story about how he had been able to, in his personal life, manufacture virality. And applying that to sort of our core mission and how do we take that and productize it and build a company around it was just very exciting. No one else really at the time was doing anything like that, especially on the digital publishing side. I think it was just a bunch of people that were excited about changing the game and challenging the status quo.

Alex Kracov: I'm curious what it was like working with Jonah. Because I've always looked up to him as sort of this media visionary. I think he did HuffPost before BuzzFeed. So what was that like? Would he just come to the table with all these crazy viral ideas and it's like, all right, Melissa, go pull it off? What's it like working with that guy?

Melissa Rosenthal: Yeah, it's exactly like that, which is why those days were amazing. We'd gather around a giant conference room, and we would have brainstorms for three hours. It would be 10 of us or 15 of us, and Jonah would just say, "Why don't we do this, or try this, or this?" We'd all come up with ideas, and we'd go around the table. We'd rattle off our ideas, and that would be kind of like our mission for the week. We'd create hundreds of posts around different frameworks and ideas. It was a lot of fun. I mean, it was a lot of laughing, a lot of crazy off-the-wall ideas. He loved it, you could tell. There's definitely no like, "This is off -limit." It's like, "Let's try it." And I think I've always stuck with that mentality too throughout my entire career. He never put down an idea even if he didn't think it was going to do well. Because it was like, how do we build the framework? We never kind of know. And yeah, it was definitely, it was awesome. It was very inspiring being around him at that stage of the company.

Alex Kracov: I feel like that mentality of, "All right. Let's just try things," was kind of what made BuzzFeed work. From my understanding, you guys just published a ton of stuff every day. And then it was sort of like throw spaghetti at the wall, see what sticks, what goes viral. Or was there more of a scientific method to kind of pair through it? How did you think about that experimentation process as you scale?

Melissa Rosenthal: Yeah, I mean, we definitely pulled up the dashboard. They had kind of built this really amazing viral tech dashboard that shows the rate of virality - the rate at which things were being picked, being taken off, where they were being published, where they were taking off, where they were being shared - which really kind of helped us then develop those frameworks. We were able to see that identity post work better on Facebook. So we would kind of have a team that would be dedicated to focus around Facebook one week. We found that, at the time, there's a company called StumbleUpon where it was like just beautiful images. It's kind of what you see on Instagram today where it's like the 10 places in the world that you didn't know exist. That was literally what StumbleUpon was back in the day. So we would optimize a bunch of team members to kind of go after that. There was, you know, what would go viral on very specific sites, that would pick it up and then share it with each other. So we definitely, over time, started developing frameworks based on what emotional framework worked and then where it worked. That's sort of how we built then that product, that machine, that then would go on to really develop a framework around what worked over time.

Then there would be just big wins. We would kind of act like a newsroom definitely. Where if something happened in the world, we would decide how we could respond to it. Unfortunately, in this country, there's a lot of mass tragedies. I think people don't really know how to deal with them, especially in a way of communication. Back then, it was like, what do we do? So we created a bunch of posts that were kind of like the 15 photos that will restore your faith in humanity just personally to be able to uplift people when bad things happen. We found people commenting and tagging each other and sharing that on those days. I think it was just like this kind of joint moment of unity within sometimes a very fractured country. I think that really kind of worked very, very well because it just brought people together. And yeah, we took a lot of learnings from examples like that.

BuzzFeed's Frameworks for Viral Content

Alex Kracov: I'm trying to think back on all the BuzzFeed posts I interacted with in the past. I think you did such a good job getting into people's psychology and what would resonate with them. I'm Jewish. I have a Jewish mother. And so you would do a post, like 10 Things an Annoying Jewish Mother Would Do, Nag you About or something like that. It's like, oh, okay, this makes me laugh. I identify with that. I'm going to click it. And I think, yeah, you guys did such a good job of that. It must have been fun thinking through every demographic, each person. What content could I put in front of them to get them to click? Is that kind of how you would think about it?

Melissa Rosenthal: Yeah, it was, you know, why does this emotionally resonate with someone? Is it funny? Is it nostalgic? Do they see themselves in it? Do they see someone they know in it? And sort of built upon that. Is it like an inner rivalry with why LA is better than New York? We would just kind of take these tropes of how people like to communicate in person and kind of extrapolate that to how do they share content, and why do they interact with it?

Alex Kracov: How did you think about BuzzFeed's relationship with Facebook? Because I know there was other platforms. But I think eventually, my understanding of it, Facebook algorithm was sort of the main way to drive traffic to BuzzFeed in both the rise up and sort of fall down. I don't know. Were you studying that algorithm all the time? How did that sort of work? How did you think about them as a partner?

Melissa Rosenthal: Yeah, I mean, we definitely viewed them as a partner. We viewed it very complimentary. We were effectively - they were the rails in which we ran on, right? Like, we were the train. They were the rails. We felt like that was a pretty complimentary relationship. I know Jonah would have meetings quarterly with Mark to talk about what products they were rolling out, what new features looked like, what they were going to prioritize in feed. Yeah, I mean, it was definitely a symbiotic relationship for a long time, where we would study what would work and why things worked on Facebook. Of course, we kind of became obsessed with it because they definitely fed us. For a good amount of time, we started to really see social sharing pickup. I think Facebook can attribute whether they decided to at some point turn that off. It can attribute a lot of our growth to their own growth in terms of building their product and getting people and their daily active, monthly actives up. Because people were sharing content on Facebook, it became our primary driver of growth over time. Absolutely. So yeah, there was definitely a reliance on it. And definitely, I think we kind of helped each other grow at that point.

Alex Kracov: Yeah, it's so interesting. Because I think, eventually, Facebook turned things down for company pages. I mean, I remember these running company pages myself at the time. It was like, oh, wait. Now I got to pay to play, to boost the posts and things like that, which is tricky. I guess it's interesting, as you build a business on the back of platforms, how that sort of evolves.

Melissa Rosenthal: Yeah, which there's actually this LinkedIn documentary about my career coming out tomorrow, which is very much based on that exact thing. Kind of what happened, why it happened and what sort of that catalyst moment was. But yeah, the reality was we definitely, for a long time, kind of believed that that was the future, and nothing could happen. There was this one moment where there was a company called Upworthy. Upworthy started publishing a version of like what we were doing, except it was-

Alex Kracov: Like spammy BuzzFeed, I feel like. Yeah.

Melissa Rosenthal: Spammy BuzzFeed. It was this clickbait. Like, "You'll never believe what happened when this witch walked into a school." Very weird stuff. It was curiosity gap that allowed people to click on it, that made people click on it. But the delivery of that was not the same payoff. Just like the payoff wasn't real, which was very much like in contrast with our belief system of how we would build content. Where whether you liked it or you hated it, there's still like a payoff to it. Where Upworthy was just spam to get you to click. We saw this dominate in feed overnight. And we sort of like had this emergency meeting and we're like, "What do we do here? Do we start doing this? Is this like a format that we want to try? Or do we think that, over time, Facebook will penalize them within the feed?" They ended up doing that after I think a few months of this. We sort of did an acquiesce, and we kind of just stayed the course. Then Facebook just killed Upworthy. One day, immediately, they banned all Upworthy links. Their traffic just plummeted, and they died overnight. That was sort of like this celebratory moment for us. Because we're like, "Yes, the good guys won." But for me, it wasn't exactly completely celebratory. Because I was just like, well, if they could do that to Upworthy, they could also do that to us. And when their priorities cease to align with ours at some point in time, what's to say that they don't start to de-prioritize this in the feed? And that's exactly what happened. They deem that personal sharing of photos and birthdays and relationship-based content would be more valuable. And that's what they did.

Alex Kracov: Yeah, this is what's so interesting about just working in tech and new media. It's like just ever-changing landscape. It's what makes it a fun but hard game, is how I think about it. Especially as a marketer, it's like you're always trying to find the alpha. What's the best way to grow? The old channels quickly get dried up and then the platforms change under you. And what worked 10 years ago definitely doesn't work today. It makes it hard. It makes it fun and hard, yeah.

Melissa Rosenthal: Yeah, I mean, the reality is like you still play that game of B2B or in product, right? But when your entire product is content and advertising-supported, you can't exist. So it's obviously just like switching industries. You're playing the game differently, which is fine. But yeah, when the entire product is just content, ad-supported, you live by the platform, die by the platform. You know, it makes it a lot harder to exist.

Alex Kracov: Yeah, it doesn't hurt as bad B2B. I feel like LinkedIn's algorithm definitely changed. Was it last year where it was like, all right, less organic reach from posts? But now you have thought leadership ads where you can promote it and put money behind your stuff. It's like, okay, the game is lightly shifted. You just got to pay attention to that. Then that actually has been working pretty well for us. So eventually, you built out this branded content division from scratch that I think grew to like $50 million in revenue in three years. Why branded content? Why did you land on branded content as sort of the main focus for BuzzFeed's revenue? Because I assume there was sort of a bunch of debate in different directions you could have gone there.

Melissa Rosenthal: Yeah, so shortly after I joined full-time, they hired a president, John Steinberg. He was a Google ad salesman for that. He came in, and his job was to monetize the company and the site. We tried a lot of weird things. To start, we tried selling caffeinated beef jerky and buckyballs. Then buckyballs started having problems, where young people were swallowing them and they were attaching to their organs so they had to have surgery. So we decided not to sell buckyballs. So, a lot of affiliates, weird affiliate things that we tried. Then we created a partner network where we created, promoted. We created and promoted ads in the feed that were other pieces of content from other sites. We felt like we could create a cross promotion network where we'd feed them traffic, and they would pay for that. We kept that going for a while. But the reality of it was, we sort of looked back to the drawing board. We didn't want to crap by the site with banner ads and traditional static ads. Just like it's a shitty user experience, where you're trying to load something and you're hitting it. Your thumb is too big, and you're hitting the ads and then the ad expands. We just felt like that was so incongruent to a good user experience for product. We viewed content as product that we decided to kind of go back to David Ogilvy's way of thinking about advertorials. That's sort of how we landed on branded content. The reality was that - it's so funny to say this now because it's just like it's so table stakes - ad agencies and companies and brands had never ever done creative content. Content was not an advertising product. It just didn't exist. It was banner ads, standard units, TV ads, all of the traditional ways of advertising. But nothing social or branded content existed. So we had to like walk into advertising agencies and companies and brands and say like, "Hey, this is the future of how people will share advertising. We believe this. It should be native, and it should feel very in line with the content that they would consume on a daily basis anyway." But that was a battle. It was a really big battle because they didn't have budgets allocated to social. They didn't even know what social was. Social didn't exist in its current form. So it was definitely a hard thing to basically rewire an entire industry's thinking on how they reach their consumer. And also, a lot of them didn't want to think that way. Because you have the people that want to change everything and we're very excited to do that. Then you have the old school way of thought. It's like, "This will never work. We don't work too comfy, and everything is good. Let's not shake the cage here." Yeah, so it's challenging.

Alex Kracov: I've worked at an ad agency as sort of my first big marketing job. And yeah, we would go in and pitch stuff. But we actually realize, all right, we actually have to educate them on Facebook. Like, what is Facebook? Because you would get these stupid questions basically from them of like, "Wait. So there's this thing and that?" You're like, "No." It was just like, oh, wait. This is like talking to my mom essentially that I got to convince and teach them, and then I can sell them on the value of it. But yeah, it's such a funny thing. Then one problem I definitely encountered too was like, "Make this go viral." Right? And I assume for BuzzFeed, that was probably so annoying. How did you overcome that?

Melissa Rosenthal: Oh, my god. My PSV from BuzzFeed is the two things that we would hear, which is, "Make this go viral. Let's make it a meme. And the idea isn't big enough." We had - I will not name them - brands, big brands come to us and be like, "Turn this into a meme." It's just like that's not the way the internet works. What we can do is we can pick up on something that's already going viral and apply it to a framework in which we can incorporate you. But we can't just like - it's going to look forced. You can't force a meme. It's like, you really can't force a meme. People see through it. They're like, this is advertising. That's just not how it should be. The biggest challenge is just you're working with us because you understand our voice and you believe in our way of thinking. Like, let us put the foot on the gas a little bit and take control of what we're doing here. Because we're going to be best served when we can have a little bit of authority and how we position you within this format and this framework. Some companies just couldn't do that.

Alex Kracov: Do you have a favorite campaign that sticks out from the brand and content side?

Melissa Rosenthal: Yeah, a bunch. There was one campaign for GE where we turned the site into a time machine, where we then wrote BuzzFeed articles from the '20s, '30s, '40s, '50s, '60s, '70s and the entire thing flipped. So you could just see what BuzzFeed would look like in the '70s or the '60s. And it was just so cool. It was really creative. People loved it. That was great. We did a campaign with Beavis and Butt-Head, for the movie, where we had them basically vandalize the site. Every post was vandalized. The site, we had it crossed out with graffiti and had it called ButtFeed. It was like very native-

Alex Kracov: That's very fun.

Melissa Rosenthal: -like you would expect on site. It was like the perfect advertising campaign. Another one we did with Purina, it was called "Puppyhood." It got 30 million views. They just turned it into a movie. We did some really great stuff. So there were definitely companies that allowed us to flex, and it worked.

Alex Kracov: I even remember it now. This is the era of big site takeovers were such a thing. I remember doing those. That's like, yeah, wow. I forgot all about that. I haven't thought of that in years. I'm sure it's still a thing. But yeah, that's funny. Then I assume, like, was your ROI that you would say to them, was it like direct response or brand advertising? How would you sort of prove the value of these things?

Melissa Rosenthal: It was organic and viral lift. It'd be like, "Hey, we seeded this on the site as a result of the 100,000 impressions that got 30 million views and 50,000 shares." That was like during the time when Facebook was so aligned with us that things would get like 50,000 shares. So the ROI on that, they didn't fully understand it. But we're like, "Look at these numbers. 50,000 people not only clicked like. They shared this out with commentary to other people." So I mean, it was very easy to show it. It's still hard to explain it perfectly of like how this goes back to building brand and how sentiment grows and all of that good stuff. But yeah, I mean, the ROI was easy to show.

How to Get Better at Brand Creative

Alex Kracov: I'm curious. Like for you, personally, why are you so good at creative? How do you come up with ideas? What about you and the way your brain works? I don't know if it's like, do you have a strong framework or just good natural instincts? Like if you thought about it, you know, yeah, why are you so good at the creative side of things?

Melissa Rosenthal: That's a weird question. I don't even know. I think I'm like an oddball, and I just like to think about weird, funny things that I find funny that maybe work. It's also good having a great creative team. Because then if your ideas are shit, they can tell you that. But we had the best team and bouncing ideas off of each other. You could just know that they were good ideas. These people had just very - there's like an intuition I believe in creativity that you know when something's a good idea versus when it's a good idea in the room and not a good idea to put out to the public. I felt very strongly about our Super Bowl ad too. Imagine when you see Super Bowl ads. There are so many of them where you just wonder like how that went out the door and what the conversation was internally, where people thought that that would resonate outside of the room outside of just being like costing a lot of money and throwing a lot of celebrities in it, where the concept, there wasn't a framework. If something is 30 seconds, there's a lot of mental leaps that you have to go through for people to understand what's happening, understand the brand impression touchpoint recognition, and have to tell a story. That is f*cking hard. I don't know if you can curse. In 30 seconds, it's so hard to do that in 30 seconds. There's a lot of opinions that go in, and there's a lot of people I think that think things are funny internally that then don't translate outside that door. I think the key to creativity is having that, like, we think this is funny. But it probably won't resonate. I think a lot of that BuzzFeed framework really helped me understand psychologically why things resonate with people and like does it have those touch points of what will make it resonate. That's really helped me throughout my creative muscle.

Creative is definitely a muscle. We were also encouraged to be creative at BuzzFeed all the time. Even on our team, we would do little pranks to see if they could go viral. We saw this trend on Reddit start to happen where people were eating weird food on the New York City subway, like eating cheese or just eating things that you don't want to eat on the subway. I got out with my team and I was like, "Hey guys, I have a good idea. Let's have one of our team members bring a full oyster shucking station out of his bag and start shucking oysters on the subway. Then we'll film it from behind one of the poles. Like voyeuristic. Like, oh, we caught this guy doing this disgusting thing." Then I have someone on our team that had some good Reddit karma post it, and it went viral. Our news team came to us and they're like, "Hey, so we have to kind of cover this. But we realized it's actually you guys that did it. How do we handle this?" It was just like, that was such a perfect full circle moment. It's like, we can manufacture virality even from our own team to be something that has to be organically picked up by our editorial side as well. Because it actually went viral.

Alex Kracov: That's so fun. And yeah, oysters on the subway. That's a good, gross idea. I'm curious, like, on a personal level too. I mean, you went from an intern to a people manager. I don't know how big your team got at BuzzFeed, but I think pretty significant. What was that like? How did you learn those manager skills? What was it like managing a big team of creatives? How were you able to sort of scale yourself as the company grows Because oftentimes, people get layered and they don't end up in that position.

Melissa Rosenthal: Yeah, I mean, they tried to layer me three times, and it didn't work. Those people are just like, it wasn't innate to them what we were building. I had been there since day one. I think that happens often. You try to layer people with outside experience, but that experience isn't congruent to how that company should grow. The people that are actually best served to grow it are the ones that have been there since day one, that have deep innate managerial skills or skills that can be worked on and grown. Those are the people you should identify early and grow those people. Then I've also taken that framework away from my entire career. That's how I've built people and grown teams.

But the reality was, it was really hard for me. I was put into a position very early where I had to manage my peers. And without my own experience, that was hard. I mean, I don't think they loved that for sure. I tried to be the best manager that I could. I tried to have a good culture and say that like, "Hey, I'm working. I'm not just managing you. I'm in the weeds with you." You know, I think, over time, I got better at that. I gained respect, and I gained trust. It became easier. But it was very hard at first starting to manage a team of people that are both older than you or your same age from kind of like overnight. You were their peer, and now you're their manager. I think that's hard for anyone. It was hard for me. Absolutely, it became lonely. I had to seek out different resources and different people. It becomes an entire new layer of change within your own growth framework. And to be able to build on that is something you often need to figure out yourself.

Alex Kracov: Yeah, I had a similar experience at Lattice. I was like the first marketer and then I end up being in a team of 20. It's very interesting because the job changes every six months. And so you have to change how you approach your actual job. You want to sort of keep going. I had the same thing of, like, kind of try to get layered. I was like, not having it, you know. Like, how do I work? I think it comes down to so much of that mentality of, I'm going to be in charge here. I'm going to work and I'm going to do what it takes to kind of lead this division or department, you know, whatever it is.

Melissa Rosenthal: Yeah, I was just very young. And being young, it's hard because work was kind of my family. I lived it and breathed it. I was working 24/7. To kind of then have to be isolated and understand that you can't do the same things that you did if you were their peer as their manager, it's just hard when you're in your early 20s. It's just a very challenging time to go through a transition like that. But if that's what the path is that you want to take, it's a good opportunity to do that and learn that muscle very early and do it fast.

Joining ClickUp

Alex Kracov: All right. Let's switch gears and jump forward to your time at ClickUp where you joined as the chief creative officer, I think, in 2020. I'm curious, like, why did ClickUp need a CCO?

Melissa Rosenthal: So, ClickUp, there's a lot of reasons why I sort of joined as CCO. One was, I was at first interviewing for CMO. I didn't really want to be a CMO. I saw CMO. 10 years are just like very, very short. The pressure is enormous. They're tasked with things that I don't actually believe like a CMO should fully be in charge of. I think there's definitely a healthy separation, or not healthy separation but healthy balance between performance and brand. Those things can be married and have overlap and a great relationship, but they can't be tied to one person. One brand, I just don't believe, is capable of being the creative person if you really want to grow a brand and also just heavily performance focused. So that's sort of the lens that we took. And it worked really well actually.

But the company believed in becoming a legacy company. We'll be like, "Hey, we're the most crowded space next to CRM. We're going up against 15-billion-dollar, 20-billion-dollar market cap companies. And we realized that it's hard to compete on product alone and that building a very unique, bold, standout brand is going to be important for us. They liked my BuzzFeed background, which also attracted me to them. Because when they reached out, I was like, "Why are you reaching out to me for this role?" They're like, "The BuzzFeed experience is actually very interesting for us because we want to build a brand that's really great and stand out." Zeb is his own brand. He's also very bold and bright. The connection was just very perfect. I was like, I think that this company will let me apply my learnings and my skill sets in a really unique way. And they did.

Alex Kracov: I think one of the main ways that I remember you doing that was like your billboards. I saw them all around the Bay Area. I was putting up billboards too, generally, at the same time. I think it was like, "One app to rule them all." Like the Lord of the Rings play, "Save a day every week," something like that. I remember looking at them and being like, okay, these are very high level, kind of over-promising. But I remembered all of them, and that makes it successful. And so, why did you take that approach? Because looking at the billboard, I wouldn't actually know what ClickUp was necessarily. What was the thinking behind that campaign?

Melissa Rosenthal: Yeah, I mean, both of the billboard is just, it's the greatest way that you can place yourself directly next to your competitors, on the highway, at the airport. Physically, to put yourself next to a $50 billion market cap company when you are nowhere near that is beyond the best medium. There's no other place that you can really do that. So that was the thought process there. We started slow. We started in a couple of markets and then we expanded.

Then the campaign itself, the goal is not to have people know exactly what you do. It's to capture their attention enough where they go to your site and look you up. We put ourselves in the right markets. Where we knew that if we could convert a fraction of them or more of a percentage of them based on that second stat, which is, "Hey, this captured my attention enough to go Google it or go to the site," and then, "Oh, this is actually interesting. I'm at this type of a company because we've targeted those areas and this is a useful product for my team," Great. Yeah, I mean, I think that's the entire goal of a campaign, on a billboard campaign. If you're not capturing their attention or creating a curiosity gap, which is also a big part of it, or creating some sort of like very grand promise, then you're not making an impact. Some people hated them. We got so much slack on Twitter. This one guy just really hated them. He would just talk about them all the time. It was great because he had a 100,000-person following. Every time he would tweet how much he hated these billboards, we would get a ton of people coming from his tweets to our site.

The goal was to create conversation. That's really what the ROI should be. If you're creating conversation and people are talking about your billboards, you've won. Someone the other day on LinkedIn had a post go viral. It was like Tesco's billboard campaign. He wrote this whole post, and he posted all these photos. I was like, you know they've won. And you know, because you have written this post, it means they've won. I don't care if you like it or you hate it. But this is the action that should be taken by creating that campaign.

Alex Kracov: I totally agree with you, too. I think billboards are so underrated for up-and-coming B2B companies. Because B2B, it's all about building trust. You know, it's like nobody gets fired for buying IBM or whatever that old saying is. It's like if the CFO or whoever sees the billboard on the highway, they're like, "Okay. This company is legit enough. They're big enough. I'll buy from that startup. I put up billboards when we were like a million ARR company, you know." That's cheaper than people think too. You don't have to do the million-dollar buy, you know, something like that. It is very underrated. I'm excited to put up some for Dock.

Melissa Rosenthal: We also like, we strategically bought them during COVID, so we got locked in. And I was like, okay, people are going to come out of hiding. It's going to be great. So we bought them and then we locked ourselves into really, really great contracts where we got a ton of free inventory. The rates were like 2020 rates for four years. So it was like right place, right time too.

Alex Kracov: And what markets did you put them in? How did you think about that? Was it just like the big cities, tech cities? Was it kind of that simple?

Melissa Rosenthal: Yeah, we tried four cities to start and then we did - it was kind of great because the company had not really been doing performance marketing at all or any sort of like marketing, marketing. They were just testing the waters, but they didn't have any good ads. So I was like, okay, awesome. We're going to do baseline aided, unaided studies, and we're going to start. It's like kind of a clean palette because you really don't have anything that's going to gray that. We were able to see like, hey, we went from, over the course of two years, from less than 1% awareness to 7% or 8% in all of these markets pretty quickly. So we doubled down. It was working.

Alex Kracov: I'm curious what your creative process was like for setting up these billboards at ClickUp. I remember at Lattice when I did the billboards, like too many cooks in the kitchen. Everyone wanted to have an opinion about what it was. I was coming up with the creative myself. I would literally like go by people's desk and be like, "What do you think about this?" How did you get buy-in? Was it a small team, big team? What was the process like?

Melissa Rosenthal: Yeah, it was a small team at that point. So it was very easy. As we got like later stage, it got much more complicated. Because we wanted to change it, and the refresh was just - it was hard. But yeah, I mean, it was based on conversion metrics on our site, too. We had those headlines as tests on our homepage, and they were converting very high. We liked them as campaigns. We thought, hey, you know what? If they're converting very high, we've tested them against 50 other headlines. These are the ones that continue to win. Let's try it. And it worked.

Alex Kracov: What other campaigns did you work on from a brand perspective? You did these billboard campaigns? What other things were memorable at ClickUp?

Melissa Rosenthal: We did a very large campaign around the idea of returning to office called "Returning to Work" where we created like 15 different scenario skits, where it was like co-worker interactions and what that would be in the way in the world of RTO. We were just like, hey, how do we capitalize on a moment unified in time that may never happen again, where every single person is talking about work collectively in the same way and can relate to the same things happening? So yeah, we created a whole video campaign. We used them as performance ads. We highlighted different roles within the company and what they would be dealing with. And yeah, it was great. It worked really well. We ran a lot of different cuts of it on different channels. We got picked up a lot of different places as well.

Clickup's Super Bowl Ad

Alex Kracov: You also did Super Bowl ad, I think, too. What was that like?

Melissa Rosenthal: That was hard. That was hard. Very rewarding and very cool to do that and be able to have that experience, but that is very challenging from every single aspect. I mean, we did it strategically. We didn't spend probably whatever the other company spent. There's ways to optimize your spend there. But I think the hardest thing, and I say this all the time, is everyone has an opinion on the Super Bowl ad. Everyone. And there were people that would come and be like, "Yeah, I texted my friend and he hated the ad." Great. What do you want me to do about that? And it worked really well. People loved it. The sentiment was 99% positive. People really resonated with them. They thought it was very clever, creative. It got our product across. It got our brand across. It was memorable. It had a framework where people understood it. But yeah, you get a lot of those one-off Slack messages. We did a lot of testing too. We did a ton of user testing where we tested - we actually filmed two different ads for the Super Bowl. We tested them against each other and pick the winner. One of them ran as an Olympics ad, and then one of them was our hero spot for the Super Bowl. But yeah, it's hard. Opinions are the most challenging thing. Because everyone can have an opinion on marketing.

Alex Kracov: And I think one opinion that really matters is the CEO and Zeb. And I'm curious. What was your relationship like with him with these different campaigns? Was he super involved and wanted to control the message? I assume there's a lot of managing up. Am I experiencing this type of stuff? That was definitely the case.

Melissa Rosenthal: Yeah, he was heavily involved in every single piece of creative that went out the door, at least to start to. He was heavily involved in this. I'm sure you can, if you ever interview him, you can ask him about the dancing, twerking duck one day.

Alex Kracov: Okay. All right.

Melissa Rosenthal: But yeah, I mean, it was like definitely a creative process that he was heavily involved in. He liked the ad. We had tested a bunch of other kind of through history ideas. We did a big campaign around whiteboards with cavemen. We liked the idea of inserting ClickUp in history. People already sort of knew and could easily - that was sort of our first piece. It was like, how do we create something that we can insert ourselves in that people already have a mental framework around, whether it's a time period, whether it's a historical event? That sort of eases up psychologically how you can connect with the ad itself. Because you're not spending time doing gymnastics trying to figure out what you're looking at. That was a big part of how we thought about kind of everything we created at ClickUp. It's like, where can we have the least pressure applied to the connection to start?

Alex Kracov: Were you doing this all in-house? Was it all people who work at ClickUp? Did you rely on agencies? How did you think about kind of building the brand team?

Melissa Rosenthal: No, I don't believe in hiring external agencies, at least for creative. I think that team needs to be very, very embedded within the brand and the framework and have been working with the CEO for a long time to have that trust and gain that trust. Yeah, we built the whole team in-house. A lot of people actually from BuzzFeed that I hired were people that understood people and human interactions and why things resonate. You know, they were certainly the core of a lot of the creative we built. Having that team was a secret weapon, absolutely.

Alex Kracov: What does the brand team look like? A creative director, a copywriter, design? What does it look like sort of at the beginning maybe for early-stage companies and then as it scales?

Melissa Rosenthal: At the beginning, it was very, very small. I believe we had a few copywriters, motion graphics designer. No creative director. We had brand manager or creative designer. Then we expanded, and we hired video people. We hired more creative writers, more - what else did we hire? Social folks, like, you know. Then it kind of expands to like, how do we think about channels? How do we think about brand distribution? How do we think about what we actually needed in-house to turn this into a machine? Then we scale through that.

Alex Kracov: Very cool. I find most B2B founders, especially if they have a technical background, are scared to invest in brand. It's like this mystical thing that they don't know what to do there. Then I always try and say, it's like, well, this is actually probably where most of your growth is going to come from, but they always just want to dump money into ad words where you could track it. You could track your bad results of that versus what I like to say. But I don't know. How do you think B2B companies should start investing in brand activities? What stage of company is it appropriate? Is there the best way to kind of dip your toe into the water in sort of these different types of brand campaigns?

Melissa Rosenthal: I mean, I think day one, even if you don't have a budget to hire an in-house team doing video to the capacity that we were doing, and I think it's still important, I think brand is also like, it's everything, right? It's tone. It's copywriting. It's images and visuals. Not even from like your brand identity standpoint. It's like humor. Like, how do you incorporate your personality into everything that you're doing? So we definitely thought about it that way too. It's like this copy has to feel like us. This asset has to feel like us. I think it's like Zeb wasn't - he didn't come from a B2B SaaS background. So I think that was actually part that really helped. He kind of knew that we needed to do this to grow and to be a legendary company. David Sacks was our biggest investor. He was behind it very much and agreed that the differentiation could also come from brand. So, you know, we had that backing. We had that support from our investors too who definitely believed that this was a good path for us and that creativity could definitely have an impact. I think you definitely need that. You need that understanding. I mean, I also wouldn't have joined the company if it was going to be a very uphill battle to be able to prove that brand had value. I mean, I was joining as a chief creative officer. That wouldn't have been very fun or very rewarding if I couldn't build a cool, fun, humorous brand or at least a brand that people would have an opinion on and know. And yeah, I mean, I think that's kind of just like the most important thing. I mean, I say this now very openly. But I think it's very hard for a company to hire any sort of leader in the brand space and not have a belief in brand. It's like, so you're hiring someone to convince you that you need to do it? That's not a very forward way of thinking. You kind of have to believe that it's going to be a lever that you can pull.

Alex Kracov: Totally. And you need to have the budget, to your point too. It's like, what's the point of hiring a CCO if you have no budget for any of these activities? It's just like waste of talent.

Melissa Rosenthal: Yeah, and we also knew that we were going to scale our performance ads quite a bit. Even the DR stuff could be creative and could have brand. And I think for a long period of time, people believed that DR is this thing that you put over in a corner. And we're like, let's have it reflect our entire ethos as a company and have all of those performance ads that people are going to see over and over and over not being annoying experience and feel very native to something that they might be watching on YouTube. And all of our ads, people love them. They were like, "This is genius." Like, "Oh, my God. Out of a sea of annoying ads that I'm served every minute on YouTube, this is a nice break."

Building Outlever

Alex Kracov: And so now you're doing something very different. You're the co-founder of Outlever. Can you talk about what does the company do? I know it's early stages, but what was maybe the insight that led you to start this company?

Melissa Rosenthal: Sure. Yeah, I mean, it's definitely that culmination of my entire career. We kind of skipped a chapter. But after BuzzFeed, I went to go help start a company called Cheddar, where we built a live media news network focused on financial and tech. You know, the reality after, I kind of knew this was the model. But again, the model was to build an authoritative voice that had trust to be able to sell advertising, mostly to B2B companies, to reach their audience because they needed to align to our authority in the market. And at ClickUp, I had a very large budget. But the reality is, when your TAM is very big, it's super hard to spend money to reach everyone. Let's just say your ICP is kind of infinite. Your TAM is infinite. Your industry agnostic, and you're trying to have all these conversations at the same time. You can't really do that. You just can't. I don't care how big your marketing budget is. It's not possible, especially internally. To be able to create campaigns and do that and track them, it's just not possible.

Outlever is definitely the culmination of both of those things. We believe that companies can own the narratives they want to own. They can provide value to people and customers to be able to give them the thought leadership platform on behalf of news. Really, that's what we do. We turn companies into their dream trade publication. We publish our own signals that we see in market that make sense for them to own and make sense for the types of things that their customers care about or thinking and talking about 364 days out of the year. It's a celebration of, like, let's get people to talk.

Alex Kracov: And so it's like, let's say, I sell into customer success as my persona. I could work with Outlever to create the definitive news source about all things customer success, the technology side of things, the coaching. That's the kind of idea?

Melissa Rosenthal: Yeah, that is the idea. I think we think about it a little bit more horizontal than that, because there are so many things around customer success that should be covered, like signals that aren't exactly just about customer success that happen every day. That, still, even if that's your ICP, we want to touch on. So the publication and the trade, what we create for, is a little bit more horizontal than speaking just to that ICP. It's a little bit more broad. But yes, that is the idea.

Alex Kracov: Very cool. Very cool. I guess, what stage are you at? Because it sounds like it's a mix of both some software technical build but then also there's clearly people involved collecting the signals and stuff. Yeah, how is it going?

Melissa Rosenthal: Yeah, I mean, it's going great. We are a team. We'll probably be a team of 15 in the next month or so. So growing pretty quickly. It's definitely a mix of product that we've built over the past year and a mix of journalists internally, in-house, and also SDR, BDRs who really understand how to create angles around certain news stories and who those angles apply best to. Also, people that talk every day to customers and ICPs that are doing interviews and speaking with them one-to-one, like hand-to-hand combat. So yeah, we're growing pretty fast. I believe we just crossed 30 customers signed. We're live with about 10. It's pretty great.

Alex Kracov: Very cool. Very cool. And what's been this transition like for you on a personal level, going from sort of marketing background to early-stage founder? You've been in the early days, both at BuzzFeed and Cheddar. But I assume it's a little different.

Melissa Rosenthal: Yeah, it's definitely different. I mean, you're creating everything, right? You're creating culture. You're creating way of thinking. You're creating your hiring processes, every framework. But it's exciting because I love that. I've done that at the core and at the starting point of other companies. And now I get to do it for our company, which is like, how do we want to go about thinking about hiring? What is our belief system over the past 10 plus years of working that we can now apply to building our own version of that? Which is so exciting because I think, over the course of experience, you create your own opinions and your own belief system on how things should operate. And now you actually get to prove that they either work, or they don't work and iterate on this. Which is just like, seeing that happen so quickly is I think my favorite part. We fail fast, and we iterate and we never do that again. We hire fast and we fire fast, which has also helped us grow and scale the team correctly and understand who really works as a part of what we're building and what skill set and what talent we need and why that differentiates us in market. And yeah, it's just been really, really exciting talking to customers every day and people really understanding how we're thinking about the world. Having their eyes light up in meetings is pretty cool. It's really great. They're just like, "Oh, I see why you would build this, and I love that." That means a lot and obviously just is great to hear.

Alex Kracov: I know. It's so fun. It's my favorite part about Dock, just seeing my weird idea come to life and then actually adding an impact and seeing. It's such a funny, complex problem too of like, "Okay. In every decision that I got wrong, it's my fault." And so you have to live with that in a way. Whereas it was easier at Lattice. I could be like, "Yeah, the CEO. That was his decision, not my idea."

Melissa Rosenthal: I think you begin to have a lot of empathy for your previous founders of what they probably were going through and their focus on every micro decision and how that matters. I mean, you get it. You start to get it. You're like, "I get why they did this or why they operated this way." It's nice. It's nice to learn like that as well.

Alex Kracov: Yeah, and I feel the existential pressure too. Like, all right. I got to make it. It's on me to figure this out, which is-

Melissa Rosenthal: Which is, yeah, isn't that the whole thing? I don't know. I like it. I think it's a good step for me. I couldn't have imagined kind of any other path, I think.

Alex Kracov: Totally. I agree. Well, thank you so much for the time today, Melissa. If people want to check out Outlever, if they want to follow up with you, where is the best place to find you?

Melissa Rosenthal: I live on LinkedIn. Find me on LinkedIn. Send me a message. I respond back within a day. I'm very quick.

Alex Kracov: Sweet. Thank you so much.

Melissa Rosenthal: Thank you for having me.