From Employee #4 to CMO: The Path to Marketing Leadership

Dave Gerhardt interviews Sylvia Lapojdevin, CMO at Kanji, about her rise from the startup's fourth employee and first marketer to leading marketing at an $850 million company. They discuss what it takes to build a marketing team and scale a company from the ground up.
I've done every single job in marketing.
My guest on this podcast went from the first marketing hire and employee number four at this startup to now they have 300 employees. She's the CMO. She runs marketing, and the company has a $850 million valuation.
I really turned from, like, execution to leadership, and leadership sounds cool, but it's really hard.
Her name is Sylvia Lapojdevin. She's the CMO at Kanji, and we had an awesome conversation about her path to marketing leadership.
It requires you to continually reinvent your. Often what it evolves into really is more of a, like, self awareness, personal reflection, personal growth.
What's actually working right now in marketing?
There's two main ways that I look at the job right now. One is internal marketing, and the other is building the team.
She told me about why paid search is working, but she wants to make a big bet in organic, but has some hesitations about what's happening with AI. We also talk about the role AI can play for marketing teams and why she thinks she might not have to build such a big team because of what's possible, possible with AI for B2B marketers today. It was a great conversation. A little mix of tactical and path to CMO. Here's my conversation with Sylvia Leutevin.
1, 2, 3, 4.
Exit. I have a great guest today, Sylvia Lapoin, who I just learned how to pronounce her name. How did I do? A minus. All right. Killed it. So Sylvia is CMO at a company called K. Canji. How do you say it?
Kanji.
Kanji. Kanji.
She seemed up on that one.
It is what it is. Look, when I was at Drift, the company was initially Drift with two T's because they didn't have the domain. And for like, four years after that, anytime somebody would write in. And then I had one of my mentors used to troll me. He's big. How. How are things at Drift? And he'd spell it, like, with three Fs and three Ts. So, you know, we don't always name the companies we work at, Sylvia. We, you know, we. We make them. We turn them into brands. Right?
Yeah. Kanji. Kanji is technically the name of the jellyfish in the world. And the founders chose it because it was easy to pronounce, which, you know, we can agree to disagree on that. But it is a unique name and the domain was available. So here we are.
All right. Yeah, I love that. That's how, like, how I named Exit 5 was like, it's a great story. And I can tell a marketing story about it, but I really just wanted to call it like you. You told me before you were OG dgmg. It was initially called the A list on Patreon. You're OG member. And I wanted to rename it, and I wanted just like a simple name. And so I was like, kind of the art of marketing is like, it's not always like you have this. It's not like a name just, like, speaks to you. And I feel like some people, when you go through product naming exercises or company, it's like, maybe there is, oh, this, you know, this Japanese phrase for whatever has been the inspiration for my life. Well, I didn't have anything like that, so I was like, well, what am I going to call it? Well, it's kind of like a place. Okay, let's come up with names about a place. Oh, Vermont. Okay, there's something In Vermont, exit 5. Like, that was how it came, you know, and I think it's funny. And then how do you talk to founders like, oh, how'd you name your company? I don't know. Just came up with it. Tom. Tom had an idea over drinks.
Yeah, people always ask about the name, like, there's going to be this grand story, and oftentimes there's not, and that's okay. And, yeah, I was an early DGMG member. And actually, now that you say a list, I think I was part of the initial A list group when you first posted it on LinkedIn. And I joined at that point, I believe, and then it changed to djg. I didn't even remember that until you said a list, and then it came back back to me.
That's so cool. Hell, yeah. All right. I. It's. It's always better. You know, sometimes I do podcasts. Like, I do podcast interviews with a lot of people, and I'm not always going to know everybody. We might not always have a backstory, but sometimes, like, you can do a cmo, you interview a CMO or whoever, and you have no prior history or no prior chemistry. And I'm like, no. It's always. If I got somebody who's like, listening to podcasts and. And is around this audience, it's always so much better. So it's a. It's a treat. It's a treat to have you and you have an awesome story. We're going to get into it. So you join Kanji. I'll get it. You joined Kanji. I'm from Worcester, Massachusetts. There's nothing I can do about. About how things come out. You joined as head of marketing when the. Your employee number four at the company, and now you're CMO five years later. And I'm calling this out because this is, like, exactly why we do this podcast. There's, like, either we talk to subject matter expert, you know, hey, we're going to talk about LinkedIn ads today. But more and more have been. Our community is about helping people grow. And I love hearing from somebody who just recently went through this crazy, crazy time. You still look amazing. Your hair looks amazing after your five years. Mine, mine, like, all fell off during that time period. So congrats to you on that.
I've definitely aged, but, yeah, yeah.
Oh, it's in there. Yeah. Right? I know. I see pictures of myself from, like, 2016. I'm like, dude, you look so young.
Every time I celebrate an anniversary, like, five years. I was like, five years feels like 50. Four years feels like 40. And it really does.
It's crazy. So, all right, so you. You joined employee number four, joined as head of marketing today. The company, your CMO, the company has 300 employees. You got a marketing team, and company just raised a Series D, and the company's valued at $850 million. So that's. That's amazing. And that's the story that I want to dig into. Just the progression from head of marketing to VP to cmo. How's that sound?
That sounds fantastic. Worked at a. I basically landed this job at this tech company called Flo Cast, and I was maybe 22 years old.
I've definitely heard of Flo Cast.
They're an accounting software company.
Okay. Yeah.
So they started in la.
That's why I knew it has a weird spelling Flowcast.
Yeah, exactly. Also, yeah, speaking of names. And I was the first marketing hire there, and that's really. That was my first big break. I kind of came in with this chip on my shoulder, like, okay, this is my shot to prove myself. And when I interviewed there, they actually told me they're like, you're the least experienced and youngest candidate that we're interviewing. So I have no idea why they hired me. Raw passion, maybe, But I started.
Okay, what do you want? Yes, I am. And.
Yeah, okay, exactly. And so I started there, and so I grew the marketing function there. And that company's actually valued at 1.6 billion now they're eyeing an IPO. They're killing it. And so that's how I started. And then, because I wanted to be a cmo, I was doing a lot of growth stuff. There. And I wanted a variety of experiences before I went to cmo. And so I went to a company called Datafox and I worked in product marketing. And that was really helpful in just kind of building out that messaging, storytelling side of my skillset. And they actually, eight months in, were acquired by Oracle. And so that was great. I got that experience. And then after, I didn't want to work at Oracle. I love building Oracle is not where I wanted to be. And so that's when I found Kanji.
Dang. Did you, did you, do you make any money in a transaction like that?
I made a little bit. I paid off my student loans and I think I paid off my car at the time, which was not a nice car at all, but it was, I'd say it was minimal. I mean, I didn't join super early there. I think it was employee 60 or something. But it was still an amazing experience. Just the experience of earning any money from your equity.
Right.
Changes your whole perspective.
No, I, I, I asked you that because, like, I talked to a lot of people who have had, like, exit events like that, and for some reason I'm always weird about asking them if they made any money. I don't really care about the amount. I'm not asking because I want to know how wealthy somebody is. It's just more like I feel like so many of us that listen, that so many people that listen to this podcast, like you join a company at some point for with.
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