Ryan Berman talks to thought leaders from around the globe in business, sports and entertainment to uncover what it means to be courageous in today's world.
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EP103 Melissa Rosenthal - Chief Creative Officer at ClickUp

Melissa Rosenthal – Chief Creative Officer at ClickUp

“The hardest days are the most fun sometimes.” First at Buzzfeed, then helping to grow and sell Cheddar, Melissa Rosenthal recently made the leap to San Diego to take on a new challenge in her career. As the Chief Creative Officer at ClickUp, Melissa is taking a bold approach to humanizing marketing in a space where it isn’t so common. Melissa has been named to Forbes’ 30 Under 30, Business Insider’s 30 Most Creative People Under 30 and as one of Digiday’s “Changemakers” for her creative brand work.

Episode Notes

As you’d expect, Melissa drops plenty of gems on this episode of The Courageous Podcast, including a few juicy tips on what it truly takes to “go viral.” Ryan and Melissa also dive into what it means to be a small fish that “punches up”, why being an outlier is important in differentiating your brand, and how Melissa has applied both of these tactics throughout her impressive career.

Ryan Berman 0:00

This is a show about facing fear, unlocking courage, and taking action.


Speaker 2 (Female) 0:05

Courage isn't necessarily a daunting thing.


Speaker 3 (Male) 0:07

It's going to give you more purpose, it's going to give you more drive.


Speaker 4 (Male) 0:10

It feels like making a courageous decision is going to get you closer to who you aspire to be.


Ryan Berman 0:14 

It’s knowledge, plus faith, plus action equals courage.


Melissa Rosenthal  0:18

I learned that being an outlier, and kind of a small fish that punches up is really important. We would constantly poke at CNBC to the point where they started to pay attention. The minute that they notice you and start to get upset, you kind of win.


(Intro Music 0:35-0:42)


Ryan Berman  0:43

All right, I'm not going to lie, I've been looking forward to this conversation because it's like, take one of your people from the East Coast, move them to the West Coast, and they get to experience what you've experienced. I've always felt about… And this is for anyone that doesn't live in San Diego is imagine you keep your motor running at 100 miles an hour. And then, you bring it to a market that is not running at the same speed as you. And this sounds more devious, or more monetary than I mean, but I do think the streets are paved with gold in San Diego. It is an awesome place to live. People are nice. Coming from New York City, it's not that people… I don't even know if people are jerks, they're just busy all the time. So, Melissa Rosenthal, thank you, first of all, for joining me, how are you?


Melissa Rosenthal  1:39

I'm good. I'm good. I'm busier than ever. But I'm great, doing well. Thank you for having me.


Ryan Berman  1:47

Well, do you feel that way? Do you feel like, “Oh, my gosh, this is amazing. I got to learn and do all the things in New York”? Not that you're just done learning in San Diego, but you take all of that here.


Melissa Rosenthal  1:58



Ryan Berman  1:59

And how long have you been doing this from San Diego?


Melissa Rosenthal  2:01

About two and a half years.


Ryan Berman  2:03

So, for the listener, let's say they're like, “Who's Melissa Rosenthal?” How would you answer that? Give me like one minute on your New York Life, and what brought you to San Diego.


Melissa Rosenthal  2:14

Yeah, so I would say New York kind of really shaped me. I grew up there, in a sense, and in many different ways. I am actually from Long Island, but I moved to New York for college. And everything I experienced in New York really kind of raised me to be the person that I am. And I think it's just the opportunities that you have there are just very much unfiltered. And it's everything, and everyone in all places at every moment in time.


Ryan Berman  2:39

And at any time.


Melissa Rosenthal  2:42

Yeah, at any time, for sure. But yeah, I think New York was just such a very important part of my life, and why I am who I am today. The ability to see what people can achieve too. And the, I would say, limitlessness of everything there really definitely had a huge impact.


Ryan Berman  3:04

College, no college?


Melissa Rosenthal  3:07

I went to college, but I graduated in three years because I was like, “I want to be out in the real world, and actually working, and not in school.” School kind of just felt like just delaying, delaying what I wanted to do.


Ryan Berman  3:21

And then, did you know right away that you're going to the city, or that you're going into creativity? Give me a little bit of that.


Melissa Rosenthal  3:29

I'd always been really into creative things like marketing. In my free time, I would often kind of do, like, trying to get ahead of the curve, and what technology was happening, and how to market in different places. So, I was working with companies to market on Myspace. Just figuring out the web, I thought it was really exciting. I felt like there was just so much opportunity even at that stage. So, it was more just kind of like I've always been a creative person and always tried to express myself creatively. And then, finding something that I couldn't believe in would be the future of something. And then, also being able to express myself in a very authentic way was really important. That kind of was the perfect fit for me.


Ryan Berman  4:13

Probably the toughest question I'll ask on the day. Did you go quarter share, half share, full share in the Hamptons in the summer?


Melissa Rosenthal  4:21

Oh, God. No, I was not one of those people. I kind of rejected that. I go out there when my friends would want to go out there, but I didn't like… Oh, yeah, no. That really not my vibe.


Ryan Berman  4:33

It's different, though, because you were from Long Island. I could see why you feel that way. That's probably like, “Let me just get out of here.” Did you think -- and then, maybe this is an unfair question -- when you move into the city, in your mind, you're like, “Ha, home I will be here, and here we go for the rest of my life”?


Melissa Rosenthal  4:56

Yeah. Once you're there, and you just see everything that you have access to, especially it's like you climbing ranks in a company, you just kind of, like, there's no other place like this in the country, and you almost kind of like… It's a New Yorker thing to do, but you judge other people that aren't from the city. They're like, “Oh, you don't live in Manhattan, who are you?” You kind of forget there's like other things out there because it draws you in, it draws you into its own world. It's such an interesting thing to talk about because it's such like the center of the universe when you're there. And it feels like anyone that isn't in that universe isn't living, or they don't understand rigor, or hard work. It's so weird, you just kind of get yourself into this mental state of dealing with the things that aren't so great about it because there's so many amazing things about it.


Ryan Berman  5:44

I gotta tell you now, it is the ultimate, like, gave me confidence that I could do anything. It really is. If you can survive that and stay... I've definitely described New York City as like a treadmill on 10.0, it just doesn't stop for anybody. If you can get on it, and not bust your chin, you're good. And, by the way, it's just as hard to get off. So, when you finally decide to get off, tell me how this came to be, and how did this idea present itself of San Diego?


Melissa Rosenthal  6:21

Sure. Yeah. So, New York, I was ‘New York for life,’ I wanted to live there, I was actually thinking about buying a place there. And then, COVID happened, as I would say, this happened to many people. And a lot of my friends retreated to  their families, like, Hamptons houses, and then they moved away, or they went to Florida, and I was just kind of in the city with my husband. And I was like wow, “I could definitely do something different.” And I was at this really interesting inflection point in my career where we had just sold our company. So, I had just left, and we were going to start a SaaS business, me and my husband ourselves. Things were doing really well, and then, all of a sudden, it was, like, pandemic hit and no one is spending money, and advertising is not happening. Everything kind of changed for us, and I was like, “Yu know what I think? I want to finally actually go into tech and lead something creative within Tech.” I started looking around, and there were a few companies I was looking at. There were two that I was deciding between, and both were on the West Coast. I was just finally open to that after, I guess, like seeing New York in a different way, and seeing everyone leave it so quickly. I think that was also the thing, it’s like, you talk to other people that are from there, and it's like, “I would never leave New York, New York's everything.” Then, the minute that things get a little bit tough, everyone just leaves. Then you're like, “Okay, wait, I could leave too.”And, you know I think? Everything kind of happens for a reason. I made a choice, and it was a great choice for me.  I was afraid that San Diego would make me soft, but it hasn't.


Ryan Berman  7:57

Look, this is where I wish I had video for people because we're both laughing and smiling. This is my biggest fear, okay, is that… And again, I've been here now for a long time. Which is why, I'm like, “I want to make sure I bottle up whatever you're really feeling here.” My big thing now, I have a ten-year-old and seven-year-old, and my big worry is I have to manufacture character-building moments in this city. If I could start the morning, and take a box of tacks, and throw them across the kitchen floor just to have build some character-building moments for them… So, when you say, “I'm afraid I'm going to get soft,” I get it. Do you still feel that way now?


Melissa Rosenthal  8:39

No, not at all. I think that's just like your own… Get in your own head. You take yourself with you where you go. And I think that's such an important lesson. And that means happiness too. Just making a change to your environment doesn't necessarily change everything, but if you have the balance of what you're looking for, it certainly can be great. So, the balance of like, “Hey, when I'm not working, I can go take a hike by the water,” that's pretty amazing. Like in New York there's walking, but you're only… This is how I would describe it. First of all, your winters are terrible. You have a couple of months, a couple of nice days, you're working most of that time. And then, the rest of the time, you're kind of going from box to box. That's how I describe New York. Box, to box, to box, to box, different sizes of boxes. And that's kind of the vibe. But here, there's just so much more than that. And also, I like nature, and it's just beautiful here. I think there's just an element of that that really added a mental balance to my life outside of just going from box to box.


Ryan Berman  9:49

This may not be a fair question, but if you could go back to the conversations with your husband in New York and you've got these two options. One is in San Diego, the second one, I'm assuming, is Northern California, or maybe the Northwest. I'm sure he also gets a say, but how do two of you… What were the pros and cons for you, if you remember, of San Diego?


Melissa Rosenthal  10:17

I had never been to San Diego before, I actually romanticized LA, and I thought I would end up there. Then I'm really glad I didn't because I really don't like LA, to live there. It was kind of this, I go with my knowing, and my heart, and what is the right decision. And this company felt right, and the opportunity felt right. And San Diego was kind of like a, “Okay, I'm sure this is great, we're moving to California.” So, I didn't really know where I was actually about to live, or anything about San Diego. So, I moved here blind in the middle of COVID pretty much, and then, from there, it was kind of just exploring it slowly. I was working a lot. And yeah, it wasn't like a thought, it was kind of just like, “This feels right.”


Ryan Berman  11:05

What have you learned so far about San Diego?


Melissa Rosenthal  11:08

That you can have both, the best of both worlds with being able to work really hard with people that also work really hard, and then, also having just genuinely good conversations with good people. And I like being nicer. I'm a much more patient person, I'd say, I'm a nicer person. I first got here, and people were being nice to me at Starbucks, and I was like, “Why is this happening? Why are you talking to me.” Literally, that's the wall I had built up in New York because it was just like, “I'm focused on me, and I don't care about you.” That changed a lot here. I'm just a much nicer and more patient person. And that's who I become. So, San Diego definitely taught me that. And it also just taught me that there's a lot of… The fact that I didn't know that this existed within the US is pretty interesting. I also feel like, coming from New York, I'm very judgmental about it. I'm like, “Why don’t they have this?” Because it feels very stuck in… Not stuck in the 70s, but it hasn't evolved the way that New York would evolve, and at the speed, and the pace. It's always just very shocking to me because I'm like, “Oh my God, why isn't there like all this retail here?” Or, “Why didn't they build a restaurant here?”  I don't know, it's a very New Yorker thing of me, but yeah.


Ryan Berman  12:24

All right, let's pivot to professional. So, let's go back to, again, the cliff notes version of your New York trajectory that took you up to your last job. Give me the rocket skipping across the pond, where did you start, where did you end in New York?


Melissa Rosenthal  12:42

I started as an intern at a 10-person company called BuzzFeed at a very small loft in Chinatown. That ended up turning into a really amazing opportunity, I went on to lead the global creative team there. And my team was around 150 people, the company was about 1500 when I left, and I'd been there about six years. And I went on to then co-start a company with my old president of BuzzFeed called Cheddar, which was a new live media news network that we built up and sold in three and a half years to a cable company. So, it was a wild ride, and it was really amazing that like I had both the early startup that I was a part of that I could see develop from my own personal development, but also, from the company growing, and the industry growing, and to really shape an industry in two ways. We revolutionized it with how media was spreading, and how people shared content. And then, also on the advertising side, it was really amazing for me, and also made me believe that anything is possible. And I think having that and not having any sort of doubts that you can do something like that was really, really important for me, and really kind of led me on this path to then believe that I could go start this company with my old boss that would be successful that we could sell. It's just having that. You could go into in a million ways and be like, “This won't be successful,” or like, “There's this,” or you hit roadblocks. And then, I think once you've done it, and you've been able to successfully achieve it, then this block in your mind leaves. So yeah, so we sold that company, and then I was kind of like, “Oh my God, I don't really want to be in media anymore,” and wanted to make the shift to SaaS, to tech. And this was the right opportunity, the right stage company for me. I wanted to go back. And after selling to a 15,000-person company, everything kind of changes if you're like the hungry startup person. And I wanted to be back in the weeds, and back in the grind, building something that could be meaningful. And also, I really felt like all of my experience building brands, and kind of doing that and media, would lend itself really well for me to do it in tech because it hadn't been done in the way that I believed it could be. That infusion of personality and humor into a brand that a B2B SaaS company to make it feel different, and stand out, and differentiated. So, that's my rock skipping in a nutshell.


Ryan Berman  15:01

No, I love it. And I want to get to ClickUp, and I want to commend you because I feel like I could see exactly what you explained of what you wanted to do. You could feel the humanity, these little touches. Again, one of my buddies, his name is Brian Kramer. He says, “There's no B2C,or B2B, there's only H2H, human to human,” that’s this.


Melissa Rosenthal  15:26

Yeah. You're still selling to people. And getting in front of them with the right understanding of what they need is one thing, but making an impression, and having a vibrant, strong brand that stands out is also very important.


Ryan Berman  15:40

But let's go back to your New York days, and I want to go all the way back.


Melissa Rosenthal  15:46

All the way back. Okay.


Ryan Berman  15:47

Yeah, we're going all the way back because I feel like there's… I'm curious your take on… Obviously, just the way you talk, I really appreciate how intentional you are, and how thoughtful you are of what you want and trying to protect that. And obviously, we don't know it all, we're growing, and we're trying to do the best we can, and it can get messy. Where are you on, “I just happened to be an intern at BuzzFeed”? And to be able to see that. In your mind, where is it like, “Well, hard work put me in that position”? Ryan, were you not paying attention when I said that I graduated in three years because I was ready to get going?” I'm curious what part of that is hard work that pays off, versus, what part of that is like, “Hey, thank you universe for putting me in this company that I can be part of the rocket ship”? In your mind, what's the blend?


Melissa Rosenthal  16:40

It's kind of like twofold. I could have joined a startup that wasn't successful, but, at the same time, the reason I wanted to be an intern there is because I saw the vision of what they were building, and I was fascinated with it, and I thought it could be the future. So, putting myself in that position, no one had heard of it, it was a 10-person experiment. So putting myself in that position, to begin with, and then, working really hard. I killed myself. I would stay up till like four in the morning creating content and trying to figure out what goes viral. I threw everything I had into that internship to get hired. So, it was a mix of both for sure. And then, figuring out where I could really shine within the company was also another big part of it. I wanted to be on the business side, I wanted to be on the brand side, I wanted to lead a team. So, my first foray into management and leadership. Just raising my hand at pretty much every single opportunity that I was given there was a huge benefit because I was able to take on things that I was not qualified to take on, and it pushed me and stretched me in ways that helped me really grow.


Ryan Berman  17:49

What percent of you are brand and what percent of you are leadership?


Melissa Rosenthal  17:56

Ooh, great question. I would want to say 50-50. Because I love leading. I think I'm so passionate about building a memorable differentiated brand, that definitely fuels me. But obviously, the leadership and the team, part of it, especially in a creative role is so important that, if you're not passionate about leading and building a team to help you get there, then those two things don't work. So, I think they're just very tied together.


Ryan Berman  18:20

So, this is more a question. I have a question that I don't have answered, and I'm curious to get your answer to this question, versus I am a podcast host that asks lots of questions. So, I've been playing around with, I think you used to be able to get away being exceptional at one thing. You could just be great at one thing, and you're good. But now,like, look at Arcade Fire. Every one of them doesn't just sing, they play every instrument, they rotate. Or like Taylor Swift, even if you want to go that way. The greatest basketball player on the planet doesn't just score, they play defense. Do you feel that there's now this multiplier where you do have to be great at two things, not just one thing to really grow?


Melissa Rosenthal  19:08

Yes. I think, in general, you always have to tend to stretch yourself to try to be great at different things to be able to grow yourself professionally and personally. But I also think, now, we're in a phase where everything is so democratized, where one thing doesn't set you apart anymore because everyone can do anything pretty much. You can build an app that would have taken you years to build in two months. So, the democratization of technology in general makes people need to work harder, and to know, and learn, and grow more to be able to kind of stand apart 100%. And I think that's really interesting because it is, like, there are certain functions that you hire for, but you stretch those functions. You do that in every role. It's like, yeah, you can do this, but this, now you have to do this. So yeah, I would agree with that 100%.


Ryan Berman  19:57

So, how does that show up at ClickUp for you? When are you wearing your creator hat, your brand hat, and when are you wearing your leadership hat? Or, maybe it's intertwined, but does it depend on the group that you're talking to as well?


Melissa Rosenthal  20:11

Yeah. Obviously, if you're talking to other stakeholders, it's more of alignment, and leadership. And then I'm talking to my team on a specific project, and its creative and brand hat. And then, I'm presenting at an offsite or something, and it's leadership. You bounce back and forth. And I think that's also a really important skill to be able to have, which is like taking that hat off and being able to switch constantly. And I honestly think that… So, at Cheddar, I ran part of our brand, but I also ran sales. We structured it in a very typical way, so instead of having STRs, and VDRs, and all these different types of roles, we had a sales team, the sales team was also the account management team. Also the data and analytics team, and the creative team. Everything was intertwined,  so we didn't have the luxury of handing anything off. It was like, you just signed a multimillion-dollar deal. Okay, this is like, you get to manage it, you have to create it, you have to deal with the clients. There was just no buffer, and I think that certainly shaped my way of being able to just switch because I had to switch all the time. It was like, “Okay, now I sold this, and now I have to actually create the entire thing, like a live program.” So, it allowed me to be able to do that, build a business in a creative way that I think benefited me long term.


Ryan Berman  21:38

All right. So, you're 3000 miles away exploring the idea of ClickUp. You have a knack for hunches, it sounds like. So give me the, “Okay, hunch tells me X, Y, and Z on why this is it, and this is it for me.” Actually,  we’d take a step back. For those who are listening that don't know what ClickUp is, can you give like 10-second intro, 30-second?


Melissa Rosenthal  22:07

Yeah, of course. So, ClickUp is an all-in-one productivity platform that allows you to bring all of your work into one place so that you can work with all of your teams and your entire organization in one tool, which allows for amazing visibility into projects, collaboration. It just makes everything more productive and more efficient, and I couldn't live without it. So, I love how passionate people are about it because it really is like, honestly, the most game-changing platform for work I've ever experienced. And I've worked in a lot of them, so that was like my X. You're going to ask me my X, Y, Z. So, after I give you my pitch, my X is just the fact that the product is so superior to anything I've ever worked on. And a lot of the problems that we solve, I was dealing with in other organizations. So, to see a product that I actually enjoyed being in was crazy to me.  I need to love what I'm working in branding and building. So, that was certainly that X. The Y was the team; young, hungry, kind of not resting on like Stanford degrees. They were just building something that they were passionate about, that they knew would have legs. And just the hustle, and the work, and the mentality of it was very aligned. Our CEO is a visionary, and he's an amazing product leader, and just was building something incredible. And just like his personality too, and how vibrant he is as a person allowed me to then,  Z, be able to know that I could build the brand that I wanted to here, and it would have his support. And that obviously is a huge part of it because if you're going to enter an organization and be like, “I'm your chief creative officer, I'm going to be branding you and doing X, Y, and Z.” And then, you can't do anything, that happens a lot. I get a lot of leaders, and they're like, “How do you sell in X to your CEO?” And I'm like, “Oh, I don't really have to because he's on the same wavelength,” which is so nice. So, those are all things that made it really easy to say that this was a winner. And then, also, the company had grown to a significant amount of ARR without $1 spent on marketing. So, I'm like, “Oh, I get to add a little fuel to this fire.”That was certainly enticing.


Ryan Berman  24:18 

There's so much in there. One; the fact that it's a good product. What's the line? Nothing kills a shitty product better than great marketing. So, here's the opposite, you actually have…


Melissa Rosenthal  24:37 

Yeah, a great product to market, which is just like… That's a dream and something that I'm passionate about personally. HDR software, would I be as passionate about that? I don't know. This just like I'm all about it. So yeah, being able to market it is kind of like a dream come true.


Ryan Berman  24:54 

And then, do you have a… It's not really a zinger, but do you have a standard question that you knew you needed answered at the top, or is it as simple as, “Am I going to have the freedom to build this”?


Melissa Rosenthal  25:09 

Yeah, it's that. It’s like, “Everything you're saying is very aligned with what my next step is, but am I going to be able to do it?” And, I didn't come in there expecting I was going to have like a huge, huge marketing budget. I knew I could do things scrappy, I've always done it. But it wasn't about the budget, it was more about, “Will you let me do this? Will you let me bring the people that I need to bring to make this a reality, to build my team, to do X, Y, and Z?” And knowing that that was a real thing was a huge selling point.


Ryan Berman  25:43 

And the founder is the CEO, and his name is?


Melissa Rosenthal  25:47 

Zeb Evans.


Ryan Berman  25:49

And how long did that first conversation, were you like, “Oh, yeah, that's my guy.”


Melissa Rosenthal  25:53 

Immediately. We hit it off. We had one Zoom call, we hit it off. I talked to his other folks, I flew out to San Diego. I think the whole process probably lasted less than three weeks. So, it was kind of a knowing, and an understanding, and just a general alignment on workstyle, and everything. He was like, “This is not a vacation, this is like, we're building this.” And I was like, “I know, I've done this twice before. I understand what it takes to get there, and I understand the hard work and the sacrifice. And that's my career, and my career is my passion. I'm on board.”


Ryan Berman  26:29 

And did your husband come out to visit with you, or did you come out the first time by yourself?


Melissa Rosenthal  26:34 

No, he came out with me, and we just ended up looking at apartments that week. And then, we moved two weeks later. It was just like, ‘bam.’ I kind of like not giving myself time to think about things, because then, you think yourself into a hole. It's like, “Oh my God, I'm uprooting my entire life and everything I thought I'd be doing,” and, “Oh my God, like.” But it felt right. It really did feel right, so I didn't really overthink it. I kind of just said, “All right, let's do this.”


Ryan Berman  26:58 

Give me one thing you learned from the BuzzFeed experiment that you brought into this. One thing you learned from the Cheddar experiment that you brought into this. And then, one thing you've learned from just the culture of San Diego that you had to sort of change that you brought into this.


Melissa Rosenthal  27:13 

Okay. So, the BuzzFeed piece, I would say, is understanding how and why people share content with each other, and what it takes to emotionally connect with someone across many different types of content. And that is maybe the most singular valuable thing I could have ever learned because I've taken that every single place that I've gone, and I've become an expert in it. And building that model was a huge part of my entire trajectory. There's no other way to put that. That's like the core of anything that everyone wants, to know how to do that. So, getting a masterclass in that was definitely the thing.


Ryan Berman  27:53 

Can you give us just a little taste of what that… What is it?


Melissa Rosenthal  27:56 

Yeah. It’s an understanding of how to connect with different audiences, and what will go viral in different ways based on who will react to it, and how to tell stories in a way that can tie in humor to something that could be potentially more focused on a solution. So that's what I'm saying. I took from that to ClickUp. But, at BuzzFeed, we just spent so much time experimenting with what would go viral. And it's things that people see themselves in, and see other people in, they'll share. Things that they personally experience, that they know that others within their immediate vicinity. We used to do these posts that went pretty viral [Inaudible 28:42] we started taking an approach like pinning LA against New York. And it was just like those would go incredibly viral. Because, see, people are so passionate about the city that they live in, and they want to say that it's better than another city. And those are small things, and being able to take nuggets, and extrapolate from learning that to then applying it across content in general, is really a cool thing.


Ryan Berman  29:09 

All right. And then, Cheddar time.


Melissa Rosenthal  29:12 

Cheddar, I learned that being an outlier and kind of a small fish that punches up is really important. Punching up is incredibly important to growth. And there are a lot of ways you can punch up. At Cheddar, one thing we did is every other business news network, tech business news network is incredibly masculine-looking from a branding perspective. It's like metallic, or silver. It feels just hard. And Cheddar, we're like, “Now, we're going to make it pink and have a piece of cheese that actually isn't Cheddar. So, people are going to hate us about that and troll us.” And that was purposeful because we're like, “That's really funny. We're just going to be Swiss cheese, and people say what it is.” So doing that, building a brand that just didn't feel like every other brand out there for business news, and like super differentiating, have a very diverse cast of anchors, talking about topics that young people actually cared about. So, everything was kind of just like this contrarian take on everything we would do. And then punching up was we would constantly poke at CMBC to the point where they started to pay attention, started to get angry, and that was amazing. The minute that they notice you and start to get upset, you kind of win. So, I think punching up. And then, also being contrarian in the way that you approach things, that was the biggest takeaway that I took from Cheddar that I then applied also to ClickUp.


Ryan Berman  30:40 

From a confidence standpoint, when you have a hunch of a strategy, and it starts to pay off, you're not playing in the small sandbox. You're punching up, but you're punching up in the biggest game that there is.


Melissa Rosenthal  30:55 

Yeah. And luckily, Zeb is so aligned to that strategies as well. And we've done like a lot of punching up here, and it's been a lot of fun. And we've taken a lot of really kind of fun bets on how we punch up against our biggest competitors. And that was a great lesson to be able to take with me because it allowed me to do a lot here.


Ryan Berman  31:14  

All right. And then, what have you discovered about this market that is now you're like, “Oh, yeah, we need to add a little bit of this into what we're doing.”


Melissa Rosenthal  31:23 

Yeah, I felt like, again, I guess, as you said, X, Y, Z, but this was another big piece. It just felt like the grass is really green to be able to come in and build something that had humor in it, and like a tone, and a personality. Like, “Wow, they’re best in class B2B marketing.” I think that was just the opportunity that I saw, and being able to infuse humor into it. Like, “Oh, wow, I've never seen a B2B brand that’s actually funny.” And being funny in a smart way, not like stupid gag funny. Actually funny. And there's such a balance to strike, but I knew the team that I was bringing in could nail that. And that was very exciting. So, being able to give our performance marketing a humorous tone, and an approach. Our feature launches would have raps attached to them. Just doing things that were kind of like, “Wow, what are they doing? What's happening there? There's something going on, something in the water at that company.”


Ryan Berman  32:20 

I hear the zag to the zig. So, it's interesting, in each one of those examples… I try to be a compensated observationalist, that's kind of my role. No different than what you're talking about.  Like, “Hey, what's this thing that's going to really make this thing go? Let's observe what it's going to make…” Which is BuzzFeed, “Hey, our number one competitor, let's punch up to the point where… It's slow-cooked, but they're going to eventually notice us.” “Oh, wait a minute, they're punching back. They're spending their money to talk about us.” And here we are, again, as “Hey, like, look at all these other B2B companies, why are they soulless? Where's the humanity? Where's the fun? You could do this in a way that's funny, but not cheeky funny.” Are you constantly doing the research, and then, working back from it so you can go forward?


Melissa Rosenthal  33:15 

Yeah it's a bit of that, it's also like a bit of how can we approach this that's uniquely us? Because I think, now, we've developed it. When I first came in, it was like, okay, my Northstar is really to humanize the brand. And have people feel like they're… Especially because we're enhancing people's productivity, which is such a personal kind of best friend you could look at as like, “Hey, this is my best friend that helps me be more productive, work better, but they're also really funny and cool. And I like them.” That's what you want. You want the marriage of; the products amazing, but also, the feeling of using the product, and then, also the marketing that brings you into the product. And you want all of that to feel very, very interconnected.


Ryan Berman  33:59 

Well, for the viewer, this is the first time Melissa and I have ever jammed. This is our first we’ll ever chat.


Melissa Rosenthal  34:06 

This is our first jam.


Ryan Berman  34:09 

This is our first jam, hashtag firstjam. But I will say what's really evident to me is you're prepared, you're cool, you know your shit. It sounds like you're having fun. Are you having a good time?


Melissa Rosenthal  34:19 

Yeah, I am. The hardest days are kind of the most fun sometimes. It’s appreciating the journey and everything that you put into everything that you do to get you where you are. And I think I try to always remember that even when I'm having hard days. But yeah, I'm having a lot of fun. Our biggest user conference of the year is happening on February 28th. And we've all been heads down working on it. And it's been such a rewarding experience, and bonding. And it's been amazing to work on that even though it's been really challenging.


Ryan Berman  34:52 

Oh, thank you for letting me take you away from all of this. I appreciate you finding the time. I guess I got to ask, is there something… We always say that fear and courage are brothers. We take a lot of pride in being fear fighters. So, is there a fear that you're presently sparring with? And, by the way, this can be a ClickUp, this could be personal life, that you feel comfortable sharing? Is there a fear you're sparring with right now?


Melissa Rosenthal  35:28 

Fear I’m sparring with right now.


Ryan Berman  35:32 

Work or life, or all the above.


Melissa Rosenthal  35:34 

I think I'm constantly sparring. But, I think that's good. I think there's always… Being slightly uncomfortable is a really natural thing because it allows you to experience things that you probably wouldn't have, and it allows you to grow in ways that you might not have. I'm a very intense and passionate person, so I'm constantly sparring with everything, but it's in a healthy way. It's not like I'm just battling myself, it's constantly doing that in a way that helps me grow.


Ryan Berman  36:06 

Well, keep at it. I would say stay courageous. Does it feel like you're courageous, or does it feel more like you're curious?


Melissa Rosenthal  36:15 

I would say both. Both. I've built up the confidence to be courageous, and I’m, I think, perpetually curious. So, I think I think it's a mix.


Ryan Berman  36:25 

Well, thank you so much for coming on. Appreciate it.


Melissa Rosenthal  36:29 

Thank you for having me.


Melissa Rosenthal  36:30 

I should ask, what do you got? You got like a last bow you want to give everybody?


Melissa Rosenthal  36:34 

What do I have? I think, like, don't be afraid to step outside of your comfort zone because it will teach you, probably, more about yourself than you could ever imagine. And whether you fail, or you fly, or whatever happens, you're going to learn, and you're going to grow, and you're going to have that experience. And I believe in the collection of experiences in life is what makes your book. And I think I'm always building my book. And that's how I view my life.


Ryan Berman  37:00 

Okay, here's my last bow, which I wasn't planning on doing. And there's zero part of this that's big leaguey in any way, shape, or form. I'm so happy you're in this market. And my mentors are always like, “You're not in advertising, you're in creative business.” And like that stuck with me. I'm not a business guy, I'm not creative, I'm doing both. And to see someone like you make a courageous choice to come to this market, and dig in, and try to hit the podium on B2B companies, not just in San Diego, loving San Diego… But it makes me really… Like I said, there were people before me that came and really kind of set the pavement, and I tried to do my part. Again, I'm not saying, “Oh, look at me.” But I'm really happy that you're here, and that you're inspiring a whole generation of creators, and creatives, and creative business people to move to this market. So, you got a fan.


Melissa Rosenthal  38:00 

Thank you. I so appreciate that, and I love that too. I love inspiring people, and that's why I like talking because I just want people to know my trajectory was not the same as a lot of other people. And it worked for me. And the more that I wish I knew when I was younger would have probably helped me now, and I just want to be able to give that to other people.


Ryan Berman  38:22 

I think we're doing it.


Melissa Rosenthal  38:23 

Yeah, let's do it. We’re doing it.


Ryan Berman  38:24 

Thanks, Melissa.


Melissa Rosenthal  38:25 

Thank you so much. Appreciate it.


Ryan Berman  38:30 

Thanks for tuning in to this episode of The Courageous Podcast. If you enjoyed the show, don't forget to rate and review us on Apple podcasts so more people can find us. See you again next week.


(Outro music 38:41-38:56)



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