Building SaaS Giants: Jason Lemkin on Multi-Product Strategy, Recruiting, and Leadership | S2 Ep1

Welcome to the ZoomInfoLabs Podcast. I'm Ben Salzman.

And I'm Millie Vietham.

Today we have a legendary guest joining us, Jason Lemkin, the mastermind behind Saster, the world's largest community for SaaS founders and execs.

Jason's seen it all from founding and selling EchoSign, scaling Saster, putting on incredible events, and building a community of over half a million. In this episode, we hear Jason's takes on how to grow a company the right way, mastering multi product strategies, and why recruiting might just be the hardest part of being a founder.

He also dropped some gems on how AI is shaking up SaaS in the future of sales.

If you're into SaaS, which of course you are, you won't want to miss this one. Let's get into it.

Welcome to the Zi Labs podcast. I'm Ben Salzman with my esteemed co host, Henry Schuck. Very excited to have on Jason Lemkin, the CEO of Saster. Jason, great to be here.

Thank you.

You're a hero of mine. I've been following your stuff for a really long time.

How long, Ben?

How long? So when I joined a startup in 2013, and I mean this seriously, my CEO told me, I don't really have time to manage you, but Jason Lemkin's your boss. Read his blog post first. If he puts out a post about a process and you come and ask me about it, I'm gonna fucking yell at you.

I think the real OGs follow Jason on Quora.

So that's really. That's really OG. It's really OG. It's really OG. Yeah.

So Jason, if you don't already know him, is the founder of sa. You've built a community, over half a million SaaS executives. You run a big events business, you have an investment firm, you do a lot of things to, I think, help lift up the SaaS community. Maybe just do a quick intro for our audience.

That's a pretty good one. You know, kind of since I sold my last company accidentally to a big tech company, I've been kind of on a mission to help other founders. And so fast forward. Oy vey. 12 years, you know, we've got 10,000 pieces of content. Thousands of podcasts, 15,000 people a year come to our events. Henry came to Barcelona when we were there, and we're kind of quirky, I mean, because we're on a mission to just help other founders and executives. So it's a lot of folks produce content now, which is cool. But I do think not having a game to play makes it kind of special. And you know, I was like a pretty good founder. You know, I had, I had a nine figure exit and eight figure exit. I didn't build a multi billion dollar company like our esteemed, but I was just good enough to see who was better than me, to see the Henrys and the others. And maybe that's what's special about me is I went far enough to know the game and I had enough and I have enough respect to know the folks that are better than me like Henry. And I think that that's produced maybe a little bit of magic, Jason.

But I don't know if that's true.

It's true.

What is different between you and me other than I stuck around longer?

Well, I would. I'm gonna guess a couple things. One is we're probably equally committed. Right. But you were, you're probably even more tenaciously focused on the goal, like doing crazy M and A and bootstrapping your company and all that stuff. I was always focused on the goal, but maybe a little conservative. Maybe you built, I don't know this, maybe you built an even better team than I did, for example. That, that can be a difference. Maybe you're a better recruiter. Right. As a founder, the hardest thing is recruiting once you have product market fit. Product market fit is the hardest thing. But then after that nothing matters but the team. Right. So I don't know, but I can. I think you have a multi decade commitment. Right. And I don't know that I had it as a founder. I was still learning each time. I was insanely committed, but maybe not for 20 years. Right.

There's recruiting and there's also just like people building. And I think a lot of bootstrapped founders who are less like capital infused, that they have to actually be great at developing their people almost equally to their ability to recruit great people. Because you oftentimes, you know, I bootstrapped the company to 25 million in revenue and then I brought in private equity. Private equity wasn't like go spend everything you can to grow. They're like, this thing looks good, spend a little more and make it twice as big. And so I didn't have a heavy budget to go get the best people. I found good people who I thought I could develop into great people.

Yep. Yeah, I think it's a good point. I think when I think reflect on it, I think what my shortcomings are as a founder. Right. Which you have addressed with the best address Is it's not recruiting one management team, it's recruiting five or six. I mean, how long have you been doing. When was Zoomingfo founded?

2007.

Okay, 2007. So the average tenure of a VP, if they're good, is probably three and a half years, right? So help me with the math. What's 17 divided by three and a half? Five management teams, right? So I remember as a founder where I remember I was sitting with my board when we just crossed 10 million revenue, and I was. And we were growing 100%. I thought that wasn't good enough back then. And cash flow positive. We didn't have Saster or Henry to help. I'm like, we suck. Like, I'm comparing myself to Dropbox and Yammer. I'm like, we're terrible. But deep down, what I was really saying is I don't know that I have the energy to recruit another management team. I did have the energy. I did, But I felt that was my. I'm looking around my team and my team had pros and cons, right? It turned out, with hindsight, I had a great 1.0 management team, right? Went on to be CEO of Gong, CEO of Brett, all these. But I. But I could see the limitations like you talked about. I'm like, gosh, I don't want to recruit the C level folks. I don't want to top my team. I don't want to do this. And maybe that's a personal failing, which is to be a CEO like you, you gotta be like, constantly. I think you gotta spend 20 to 30% of your time soft recruiting execs. Nothing else matters, right? You can talk the roadmap until you're blue in the face or sales strategy, but if you don't have the team to do it at Zoom info scale, there's no point in talking to your office, right? So any of that's where I think you're better than me, among many things is you gotta. I mean, it's tiring to rebuild the management team, isn't it? Maybe you love it, but I don't know that anyone loves it.

I mean, I think part of it is, like, there's this piece that, where you go like, yeah, you should be recruiting 20 to 30% of your time all the time. The other side of it is you need to be evaluating your team 100% of the time. And so 100% of the time you're trying to think like, is this the right person? I think it's the right person. Are they. Are they doing the right things? Are they? And if they're not, how much time do I have to like, get them to be doing the right things and building a good team, or do I have to go start meeting other people? And that's probably the most tiring part because you kind of want to get your team feel really good about them. But if you're trying to build, it's like you're constantly evaluating if they're the right people.

And you got to do that. And I think if you're smart, you can do that. Anyone smart can be a critic, right? Anyone smart can be a critic. The hard part is not only doing all that, building your company, evaluating them, but then realizing, hey, Lemkin might, for whatever reason, quit tomorrow. I gotta get 20 more candidates in on Monday and not have this wreck the company. I think that's hard. And the best if we want, you know, if we get into revenue leaders on this. What I realized makes an incredible CRO or VP of sales is they've always got 10. They're constantly like the best recruiters on planet Earth is a great VP of sales because they need a bench of leaders. They need managers and directors and VPs and SVPs, and they're. And then people and soldiers are gonna fall. And the folks that were good at 1 million won't scale to 10 or 20. And they know that they will.

And.

And the hardest job is sales. Cause the number goes up all the time, right? The stress goes up. So if you're not building. And so I think the best sales leaders are even better recruiters and CEOs. And I love them. But you gotta learn this as a founder, like, you will stall out. And, you know, if you wanna talk about why founders I've invested in have come up short sometimes. Right. It's this second management team theme I see. Sometimes it hits you emotionally like it.