Jason Lemkin on What Makes a Great VP Marketing in SaaS, Working with the CEO, Lessons from SaaStr

Everyone wants a team and I've hired old folks on my team to help me. My marketing team, they're not willing to do the work anymore either. I assumed they would do the work when I, when I hired them. I mean, just as a helper, not full time. Right. But they weren't willing to do the work anymore. I need six people. You know, I need, okay, I need a content person and I need a media person, I need to earn person, I need a PR person, I need a demand gen person and I need a growth person. And each of them needs an agency because they don't do it themselves either. So you have five marketers and five agencies working for your cmo.

All right, folks, my guest today, this is somebody that I've admired from afar for years. I was. You'll like this, Jason, an OG Saster reader. I remember when it was just an email, a blog and an email, right when I first got into startups, like, that was the stuff that made me pretend to be smart about Sam Sass. I went to my first saster in 2016. I was a young marketing manager at a company called Drift. David Cancel, who's a CEO, he got put on a panel and we were like, we're going. He made me share an Airbnb with him. You know, like junior level marketer, travel with the founder. It was an incredible experience. That was a formative time in my life and as a former marketing le Leader leader, I've spent a bunch of money in and around Saster and what I'm really excited about now is that you've built an incredible brand and a media company with Saster. He's a sales guy by trade, but I think he's one of the best marketers out there. Jason Lamkin, thank you for coming on the Exit 5 podcast.

Thanks, man. Excited and excited to what sort of community you've built. I think community is an overused term. Right. It became maybe almost abused a couple years ago before AI got hot. But most people don't have a community, so it is impressive what you've done. So I, I'm, I'm a fan back now. Watching, watching what you're doing.

Oh, that's, that's amazing. Thank you. So I usually don't do any prep for these, but I was like, I was like, man, I got to bring my game. I'm going to bring my A game if I'm going to get Jason on, on. On the pod. And so I wrote all these prep questions last night and I'm going to take you through them just to give me a flow. But then I open up LinkedIn today and I see you wrote literally some of the worst senior ish sales and marketing people I've ever worked with are selling books or courses or both. You've been warm. That was like, man, that's a dagger right out of the. Right out of the gate.

You know, it's. I mean, we can talk about everyone. It's. It's just. And I'm struggling with this, Dave. I'm really struggling with how much the world has changed the last couple of years for everyone. But much more sales and marketing customers does much more than engineering or product. The world has changed so dramatically. And so you got to look. You got to look for tells. I'll tell you, I was doing an interview yesterday with the sales exec. There was a saster superfan, and I ordinarily wouldn't have talked to him. And the email exchange was kind of weird because it was both fast and slow. You know, recruiting is like sales. Like, if it's, if it's bad, it's not going to get better after they start. But it was weird. It was good and bad, right? So that's a weird sign. So I do the meeting. Super fan, super nice guy. And we're about 40 minutes in at the end, he's like, oh, I don't want to do that. I'm like, okay, why not? It's like, well, I'm. I'm looking to do at least four or five jobs at the same time now. And, like, you want to be like a fractional or a consultant? No. He's like, I'm looking for four to five jobs this time. I'm like, I don't need you on my little team, but more, more power to you.

That's crazy. You know, I was going to ask you about this later, but I can, I can sense this. You have a lot of energy and, like, the way you write, and I think you're a good copywriter. But you've, you've been writing more about this theme and these are not your words, but so paraphrase it as, you know, take it as you will. But, like, you kind of been hitting on this theme of, like, people aren't working. Like, things have changed. People aren't really working hard. There's not a lot of loyalty and commitment. There's. There's something in there. Where does that kind of narrative stem from? Is it just from what you've seen over the last couple of years?

I'm okay with it. I have a few personal thoughts. I'm more just trying to help us all, as a. As a set of leaders, recalibrate what we expect out of people. You know, the biggest tell to me, you know, there's all these vibes out there, right? There's vibes. And one vibe is, I quit. I'm out of here. Like, it's all over my YouTube feed. This whole feed. Like, I was a senior engineer at Spotify for four and a half years. This one for women. I quit it. I quit with no notice, and now I can't find a job. There's all over mine. But it's just. Where. How do we recalibrate in this world where we got to get shit done?

But.

And this is what, folks, it's not your problem. But you don't get budgets. Roughly speaking, are half of 2021. Because revenue per employee is doubled. If we have to make 400,000 in revenue per employee and it was 125 in 2021, folks, don't. You don't have to care, but you should understand this. Where's it coming from? Where's 400k in revenue per employee coming from? And I get that folks are. Whatever, they're burnout or the world's changed, or this weird world of second half of 2020 to early 2022 lasted a long time. It wasn't three months, right? It was two years of. Of insanity. But the problem for all us as leaders, as VPs, as founders and CEOs, is we truly have to do more with less. Today, there's no choice. And if folks don't want to do that, if they want to be paid 150 and up to have a team of seven to do a podcast, you're doing this yourself, man. I get it. It did kind of bother me last year. Now I get it. I'm like, but where's the money coming from? If Dave needs seven people to do a podcast, how much does that cost? And they all want to make six figures. Like, all of a sudden, that podcast is a million bucks a year, isn't it?

Or they do it and don't want you to put it under the scrutiny that it would deserve at that investment level.

It sounds like I'm a critic. I'm more just pointing out my I'm learned. I don't have. I have a lot of answers in Saster. I really think I have some good learnings over the years, but this one, I don't know the answer to. I don't. I don't know the answer to. And it's funny, I had a friend of ours that, you know, helped me. I'm trying to hire an email marketer today that can send ticket emails for us to the events. It's a good job. I can actually pay an insane amount of money for this job.

I heard you say this. I was listening to your interview with Nathan Latke and I sent it to our team because we're trying to grow our list also. And you go, I was like, I feel the same way. You basically said, like, I'll write a blank check, like, this is the most valuable piece of our business, but I literally can't find anyone to do it.

At least it's critical. But it's funny. A friend of ours that we both know or someone we both know has a great community. Not a community, but a great group of folks that follow him. And he sent this out and he got about 40 responses the other day. And then he asked them all just to do one bit of follow up. Just to come up with one sentence of follow up. No one did it. 0 out of 40. So again, it sounds like I'm being a critic, but I'm just trying to learn. There's this theme. I started saying this a while ago and it's become a bigger theme in saster, which is that you got to hire pirates and romantics. You got to hire these quirky folks that are so passionate about what we're doing, they couldn't do anything else. They can't fit in anywhere. There's. They're pirates and romantics. But tech got so big in the run up to 2019 and beyond that most folks aren't pirates. They're just job workers. And that's. There's nothing wrong with that. Stripe needs what, 10,000 employees. They can't all be pirates and romantics. But where do we find them? How do we make sure we hire them? How do we meet people's expectations? People's expectations are very high. I don't mean to take all of our time, and I say that, but I'm just still, this is an existential answer for. For all of us. We don't know the answer.

I'm happy to spend some time here. This is actually something that I wanted to talk to you about. And I have questions, other questions that I want to get to. But this was also my list and I was going to ask you what continues to motivate you? You have been successful. Like you, you know, you've had exits, you've invested Sasters a $30 million a year business or whatever it is. Like, you certainly don't have to do this, but when I listen to you talk, when I read your writing, I see you on stage at Saster, like, you have that fire. You have a drive. You're more grounded, I think in even just meeting you right now, you're more grounded than you come off online, which is true for all of us. Right? Everybody says to me, you're like, oh, they're much, you're much nicer than I thought you were. I'm like, well, is you how you thought I was or is that on me what lights your fire? Like how. What has you continuing to grow and, and build?

Well, look, I actually, I'll tell you, I didn't know that answer until like five or six months ago when I did a discussion with Aaron Levy. And I'll answer it, but it changes over time. So in the beginning you talked about the old days, right? The old days when you're, when it was a blog and an email and an event. You know, back then, like, like many of us, you want to have a sense of meaning. You want to contribute to the world. And the main reason actually I started Saster was I had guilt about selling our last startup, Echo Sign, to Adobe too early. And I felt guilt. There was some personal angst I had. But what I more felt like is that what happened was we sold and you know, for years the team kept going, especially the sales team. Sam Blonde, now Sierra of Brex, Brendan Cassidy Jameson, who's, you know, SVP of sales at Gong. These guys, even with all the lack of help from Adobe, they kept going. Like they kept growing to triple digit rates. And so I'm like, God, I kind of let these guys down a little bit, right? So I'm like, no one's heard of these guys. We're a startup that sold. I'm going to build a little bit of promo for these guys. So I'm passionate about sales and revenue, but if I do a little bit of this, then folks are going to be like, hey, I want to hire Sam for his next thing at Zenefits and Brexit Rippling or Brendan for Talk Desk or Jameson and Iran at Gong. And I think it worked. I think it did work. It created a high bit of brand benefits for them beyond the startup. Right? But that was a long time ago. That's what got me going, was not wanting to let down the team. But they're doing fine now. A few years later then I would say up until March 2020, it just became a phenomenon. The wave of passion, especially for the events. And the content was so strong, all I could try to do was, like, ride the wave. I had no strategy. It just was totally organic. Right then we had a whole reset from 2020 to 2022. And just digging out of a $10 million loss in March 2020, redoing it like it was painful, but it was intellectually interesting, right? Because you got to reboot it. That's your second act. But now I'm in the third act. And I don't know the answer, but I asked this question to Aaron Levy the other day, why do you still do box after 20 years? And he laughed. He's like, hold on, I'm not that old. I've only been doing it 18.8 years. But come on, man, you've been doing box 20 years. And we're watching Scott Farquhar just retire from Atlassian. We're watching a lot of people quietly retire this year. And I asked him why he's doing it. He said, at this scale, it's interesting. It's a jigsaw puzzle. He said, look, I've got a billion in revenue in box a year right now. Some of that goes to hosting and storage, but this is software. We have 80% gross margin. So out of that billion, I got $800 million a year to play with. I got $800 million of people to hire and products to invest in. Now, it sounds like a lot, but it takes a lot to run a billion dollar company. And I wish he said, I wish I were growing faster. I wish I could do more. But that's the fun part, is taking 800 million and playing it out. And I know it's a long answer. I am stimulated every day working on Saster because it's a jigsaw puzzle. Everything at scale is a jigsaw puzzle. I didn't get it, but now I see it. It's frustrating, but it is intellectually stimulating to be. To have something that's above a certain level.

Right?

Every day you got to figure it out.

It's like a different. If you're a competitive person and the game keeps getting more challenging and you have different ingredients in different circumstances, and you're. You're playing a new level of, of the game. You said you don't love it, which I think is something interesting. And I want to just share this story with you. So in 2020, I do think we, a lot of us in tech and SAS had that kind of like, man, is, is What I'm doing that important. Like, you know, the world is crumbling and like, here I am peddling software.

That's the Woe is me moment. This. What am I doing selling accounting software, insurance software. This is what I was put on this earth to do, right?

Like, you know, we got like, you know, my neighbors at the ER saving lives. And I'm like, saving lives. Exactly. And so. So anyway, I was CMO at this company called Privy. They got sold by Attentive. I made a little bit of money from that. And then I was VP of marketing at Drift and they sold to. And I made a little bit of money at that. Like, not one huge exit, but enough to be, like, very safe and comfortable. And that combined with the 2020 thing, I was like, man, what, I'm going to just go in the woods and like, write poetry for forever, right? And I was beating this drum of, like, solopreneur should. I'm just going to be a solo, solo content creator. This is what I'm going to do. And I had this complete pivot in my business a year or two ago where I realized, like, no, there's actually something here. I need to get my name out of it. It was initially called, like, Dave Gerhardt Marketing Group. I. I pivoted to exit 5. I rebuilt that because I'm like, oh, there could be an exit. This is a sellable asset. One day, like, I could build a real company here. I wanted to take myself out of it. And I ended up hiring people this year and investing in this business. This is the most excited and most fun I've had working like the last six months. And I'm completely re energized. I went from like two years ago being like, is this all I'm going to be the B2B marketing guys this my life to like, I'm having a ton of fun. The purpose that I see now is, like, it is fun to build something, right? Like, we're not saving the world, but it's fun to build something. It's fun to be in Slack. Send them. Hey, I'm doing this podcast with Jason Lemkin. Say, oh, everybody's like, that's fun. And I think that's the stuff. And like, having goals and growing and that's the stuff that, like, I underrated. And there was no like, t. Like, I. I needed to. To build a company and to feel that. And that's kind of given me this win. Now does that. Can you relate to that a little bit?

Well, I would say two things. First of all, I think you're a real founder now. And so what you've seen is that builders got to build. Builders got to build. There are Machiavellian founders, there are folks literally in it for nothing else to make money. But that works better in later stage parts of tech, financial engineering. Most folks that can get something off the ground to seven figures in revenue are builders. They're builders and builders got to build. And when I sold both my startups, I've never been depressed, but I was at the edge both times without building, at the edge of depression both times. Crashed my partner's Tesla. The second time, one of the first Model S's took it off. The lot just was a little blue. But so builders, builders do have have to build. However, for folks that might watch us, I do think this solopreneurship thing, even though it's, it's kind of, it's a little bit less alluring today than it was a bit ago. I hate to say this because I might get flame for it, but I do think there's a heavy toxic element to it. It's heavily toxic that I can flee my.