00:00 Welcome and Guest Intro
01:22 AI Beyond Productivity
03:42 Talent Density in AI Teams
07:23 Standing Out as a PM
09:58 Org Charts with Agents
13:18 Agent First Workflows at OpenAI
14:42 Who Can Build Now
16:01 New Scarcity Alignment
18:03 Workflows to Redesign First
20:14 Measuring AI Impact
22:07 Wrap Up and Thanks

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

00:00 Welcome Back to Never Too Early
00:32 Meet Adam Hall: Strategic Marketing & PMM Expertise
01:10 What Product Marketing Owns + How to Measure Success
05:09 PMM vs Demand Gen: Who Owns Pipeline and How They Work Together
08:37 When to Hire a PMM: Timing, Founder-Led Marketing & Healthy Friction
10:45 How to Define Your ICP: A Practical Framework for Targeting
14:14 Do You Need Domain Expertise in Your First PMM?
18:12 Stage & Org Design: Where Product Marketing Should Sit
21:45 Final Advice, Where to Find Adam, and Wrap-Up

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

00:00 Welcome and Introduction
01:21 Laura’s Journey to CEO of Descript
05:02 The Evolution of Media and Content Creation
07:41 Finding Your Authentic Content Lane
13:00 Effective Content Creation Strategies
15:56 The Importance of Authenticity in Content
20:12 The AI Content Creation Debate
21:48 Finding Your Creative Lane
23:05 Creating Authentic Content
24:30 The Importance of Consistency
28:57 Choosing the Right Distribution Channels
33:47 Final Thoughts and Advice

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

Transcript

Lauren Ipsen: What’s up, everyone? Welcome back to another episode of Never Too Early, a YouTube series focused on unconventional talent insights for founders. I’m Lauren Ipsen, Talent Partner at Decibel, and this is my Founder Therapy series.

In this series, we will cover early learnings, misconceptions, mistakes, and a whole lot more with folks that have recently taken the lead to start their own venture-backed tech companies or take a step into the CEO seat for the first time.

So, with that being said, I am beyond stoked to welcome my guest today, Laura Burkhauser. Laura was formerly running product at X and Rent the Runway before coming over to Descript, where she ultimately just took the step into a CEO seat for the very first time. Okay, Laura, welcome to the show.

Laura Burkhauser: Thanks so much, Lauren. I’m excited to be here.

Lauren Ipsen: I am really excited to have you. I can’t think of anyone better to discuss this topic in particular, so super excited to jump in. I personally love your content. And kind of fun that I’m gonna be editing all of this on the Descript. So there’s so much that goes hand in hand, and I’m excited to just chat with you about it.

Laura Burkhauser: Yeah, absolutely. I am also excited to share this on LinkedIn and our other channels.

Lauren Ipsen: Yeah, I know. I love it. Okay, cool.

So, I guess, to get started, first and foremost, I would love to just kind of give the viewers an overview on who you are, where you came from, and then if you could just talk to us a little bit about the recent role that you just took on.

Laura Burkhauser: Yeah, absolutely. Well, let’s see. I am the CEO of Descript, which is a video editing solution that makes every kind of video. So we do podcasts, we do—when, you know, you turn your podcast into clips. We do YouTube videos, educational videos. You can edit and publish webinars—all of the different videos that so many of us are feeling incredible pressure to create, whether we’re a marketing team or a founder. And we’ll talk about that.

And I found Descript. I was a customer, actually, before I worked here. So my background is, I was at—I was—before this, I was at Twitter. And that was kind of my first exposure to, you know, seeing the different use cases that people have for social media and, really, how people are using social media to craft and tell their story and to tell the story of what’s happening kind of beyond their role.

And then, when I left Twitter, I wasn’t quite sure what I wanted to do next. You know, it was actually, an interesting lull in tech. It was right before ChatGPT came out and was a consumer product. And so, when I left Twitter, I was like, I don’t really know what I wanna do next. Like, is anything exciting even happening in tech anymore? Isn’t it all just about, you know, trying to pump engagement on the various feeds that we’ve created? Maybe I don’t wanna do this.

And when you’re having that kind of an identity crisis in the Bay Area, you know that you are legally required to start a podcast, which I did. And as I was editing that podcast, I found Descript. And the first time that I deleted my filler words, deleted text, and it changed the video, I had this experience that I think a lot of us have had when we find that magical product where I was like, oh, this is why I got into product management. Like, this is why I got into tech. It was to create magical solutions like this.

And not just, you know, the experience of using the product, but also that, you know, great products, they don’t just do a job for you. They kind of transform the way that you see yourself.

And for me, someone who is, like, much more comfortable in docs and decks, to suddenly be editing video media and publishing it, I was just like, oh my gosh, I’m a creative person. And having that transformative experience made me then knock on the door of Descript. They did not have a job description up. And I said, “Hey, are you hiring product people? I do product stuff.” Like, do you wanna hire me? Yeah.

Lauren Ipsen: And now look at you.

Laura Burkhauser: I’m the CEO. So this is why you’ve always got to shoot your shot, you know?

Lauren Ipsen: A hundred percent. I think that applies to every aspect of life, and I love it. Very, very, very cool. I just think that that context is really helpful for the listeners to get a better understanding of kind of how you stumbled your way into Descript and also. why, you know you’ve found this kind of passion in creating content and amplifying it. So I love it. Super helpful.

You talked a little bit about the pressure that so many people feel in the Bay Area and just more generally around creating content now and feeling like they have to be visible and have a voice. Talk to me about where that stems from, if you have any idea. And also just more generally, as a modern-day CEO, why you feel it’s so important to be having your voice out there?

Laura Burkhauser: Yeah. I mean, it’s the same thing that’s happening in media in—in every kind of media, right? Where 40 years ago, there were just a few distribution channels, and there were a lot of gatekeepers to those distribution channels. And so, if you wanted to kind of, create the narrative of what’s happening in the world, you needed to have access to a gatekeeper, or you needed to ingratiate yourself into the people that own those distribution channels.

Now, over the last 40 years, those distribution channels have multiplied, and they’ve become a lot more democratized. And social media obviously has pushed that, you know, as far as it can go, when—you know.

And so, because of that, you see things like maybe in the old days, 20 years ago, you would try to craft the story about your product and try to own the narrative by hiring a PR firm and saying, “Can you go out and just try to get a lot of articles written about how this is happening right now, and try to get people to interview me? And give—and I’m gonna give this quote about why my company is the solution to this problem that’s been happening.”

And you try to, like, create these news stories in official outlets. And now, anyone can create a news story and publish it. But so, it’s less about, like, do you have access to the storytellers, and more like, do you have the juice, right? Do you have the charisma? Do you have what it takes to get out there and craft the story?

Because if you’re a founder, there’s probably, like, this pitch that you’ve given to a million funders and that you try to give on your website that’s like, here is the problem space. Here is the burning platform. Here’s why my product solves that. Right?

Lauren Ipsen: Yeah, right.

Laura Burkhauser: And it’s kind of amazing that you have that opportunity. Technically, you have the opportunity to go out and make that pitch to every person in the world right now. And the question is, do you have what it takes to break through? And do you have the stick-to-it-iveness to, like, keep up the momentum and keep pushing that message?

Lauren Ipsen: Yeah. That’s the hard part, I think, for a lot of people. Like, a lot of people will get started. I mean, I’m guilty of this, right? I came out of the gates with this podcast. I dropped a bunch of episodes. And then it’s life gets crazy, you know? And you’re just like, oh, shoot. I have a lot that I want to put out there, but you also have a day job for you. You’re pushing product. You know, there’s lots of other things that are happening.

So talk to me a little bit about how you continue to stay on it, push out content, and do it in an authentic way, where it doesn’t feel like you’re just doing it for the sake of doing it.

Laura Burkhauser: What you need to do as a founder is sort of , think about yourself, and think about your problem space, and think about your product. And out of those three things, you need to figure out, like, okay, what is my content? What is my channel? And what is my practice gonna be? And, like, a helpful kind of two-by-two. You can think about—sorry, I, like, live, breathe, and will die in a two-by-two one day. And, like, the two-by-two on my mind is the content charisma matrix.

Lauren Ipsen: Perfect.

Laura Burkhauser: So some people who are listening are like, I have a lot of kind of expert content, right, that I can think about. Sometimes this is technical content, so you may be working on a really interesting model. And what you have is, like, technical content about how, you know, to do research in the field today, right?

That’s one kind of content. I’ll say that my best performing LinkedIn video was a different kind of content expertise, and it was how to prepare for an interview. And it was, like, the first video that I did. But I just had been doing hundreds of interviews and was like, okay, I just have three things that I think everyone needs to make sure that they do if they’re gonna be interviewed by me.

Lauren Ipsen: Wow.

Laura Burkhauser: And I think just because everyone interviews for jobs and is hungry for that content, having someone who is an expert, even though “expert” just means, like, I’ve done a lot of interviews. I’m not a professional interviewer. That’s just part of my job.

Lauren Ipsen: Right. Totally.

Laura Burkhauser: But that was really valuable content. So think about, am I someone who—maybe I don’t think my content is valuable, but, actually, I’ve had a 20-year career. There probably are a lot of people who think that I have valuable content. And what could that be? Right?

And then I think—then there’s charisma, which is just, like, am I the kind of person that can be in front of a camera and shine? Right? Do people lean in—

Lauren Ipsen: Do you have rizz?

Laura Burkhauser: That could make up for a multitude of sins, Lauren.

But if you are, high content and high charisma, right? You can be a thought leader—someone who’s going out and guesting on podcasts and creating content where you’re in the camera—that’s great. And probably, if you know that that’s you already, you’ve already gotten started, right? Your life is on the easier side.

What do you do if you only have one of those things? And I think if you have a lot of charisma, but you’re wondering about content, I actually think podcasting is the perfect—is the perfect thing for you to do. Because, yes, Lauren, your job is to be professionally delightful and to just have people on the pod. I mean, you’re very—

Lauren Ipsen: My job is to have friends.

Laura Burkhauser: In this one part of your job, that is your second job. It’s—you have this very hard other job that you do.

Lauren Ipsen: This is true, but that job also involves just having friends, really, at its core. Yeah. Best job ever.

Laura Burkhauser: And that’s like—yeah, so you can be a podcaster. If you’re someone who has a lot of content and you’re lacking in charisma or, you know, you’re less comfortable in front of the camera, I think educational video is really where you wanna play. That’s where you see a lot of this on LinkedIn, and it gets great engagement.

That’s more like screen-sharing to teach a concrete skill. And people are very hungry for that. That gets great engagement; can turn into MQLs really easily. I think, like, Jacob Bank, who’s the Relay app CEO, has a huge following on LinkedIn right now. And he has this—like, his product, Relay is an agent builder. And he just demos for you. Like, “Hey, I made this Reddit agent. Hey, I made this LinkedIn to email agent.”

And he’s really just showing you his workflow, which is screen-sharing of him, using his product. And that’s so great. Like, what a fantastic kind of lead channel for him now to just teach people how to use this stuff.

And a lot of us who are building AI products—you know, a lot of the education you need to do and the content you need to create is, like, hey, this is the use case. Some of you, like, you know, haven’t even figured out that this exists yet. Like, let me explain what the problem is and why this solves it. And if you can weekly have content where you’re just sharing that educationally, that’s huge.

Lauren Ipsen: So I think it’s something we often consult our founders to do a lot of, and they often come back to us. And it’s exactly what you were just speaking about, where it’s like, where do I start? Maybe I don’t want to be in front of the camera. And there’s been a million Substacks that have been done, or whatever it might be. Or, you know, how do I continue to think about things that come up?

So, I guess, talk to me a little bit about how you find an authentic lane and also how you continue to find time each week. Is it as simple as putting something on the calendar? Is it as simple as recording it all at once or writing it all at once and then kind of boosting it out into the ether when times make sense?

I think these are, kind of the tactical questions that people struggle with, hence the lack of consistency, and then hence why it falls off. And I think you do a really good job of keeping it up.

Laura Burkhauser: Yeah. So I think there are a few different workflows that work. The great thing about podcasting is, like, yes, I think if you decide to go to the podcasting route, I suggest that you put a block Friday mornings or Friday afternoons, and you just commit to—you know, it’s basically a meeting. You invite interesting people to that meeting. You do a little bit of prep in advance. You promise to make everyone on your podcast look good, so that no one’s expecting an oppo kind of thing. And you—and you just, like, have a great conversation and get into your editing habit and try and time box it. And you say, I’m gonna spend an hour talking, an hour editing, and then I’m gonna publish the podcast and do, like, 10 clips that I’ll post on social.

What’s great about podcasting and clips is those clips are things that you can share, you know, for two weeks. And if you wanna do a biweekly podcast, or even a monthly, it’s, like, great. Those clips can be the thing that you’re sharing in between each podcast.

Lauren Ipsen: That’s what I do.

Laura Burkhauser: Yeah, exactly. So that’s, like, one workflow. Another workflow I see, if you’re not doing the podcasting route, that I do sometimes is, you know, I’m in a studio right now. I haven’t done my hair and stuff like that. But sometimes what I’ll do is I’ll get in the studio because I have—there’s good lighting and a good camera here. And I’ll just like—I’m—so I think, like, either you’re kind of an improvisational person or you’re a scripted person.

I’m often improvisational. And so, I will, like—this is actually a fun hack. You can use ChatGPT voice mode and ask it to interview you on a topic ,and it kind of plays the interviewer kind of character.

Lauren Ipsen: No way.

Laura Burkhauser: Yeah. And you just talk to it about—like, I can say, like, “Hey, can you, you know, ask me a bunch of questions about how to build great product or how to build a really strong product team.” And it’ll just toss a bunch of questions my way, and I just answer them authentically. And then I can go through and edit it and find the clips, right?

Lauren Ipsen: Wow.

Laura Burkhauser: And it’s like, oh, there’s a clip. There’s a clip. Oh, I sounded like an idiot there. Let’s just delete that and never speak of it again. And so that’s, like—that’s a really great workflow. If you just wanna, like, okay, I’m gonna sit here for 30 minutes. I’m gonna talk to my computer and just kind of, like, riff. Right? And a lot of us are good at riffing.

Lauren Ipsen: And no pressure. And, yeah, I think that also helps with what different ideas can I speak to. And, also, I think naturally, when you’re doing your job, whatever it is, all day, every single day, you start to forget that you’ve got a lot of knowledge, and you know what you’re doing, you know? And there’s a lot that people can learn from whatever your craft is.

And so, yeah, sometimes it’s just taking a second to have someone else ask you questions, and then you realize, oh, I actually do have a system to that. Or, oh, I actually do have pretty strong opinions on some of this stuff. Right?

Laura Burkhauser: Yeah.

Lauren Ipsen: So I think that’s a great hack. I’m for sure going to use it, and I’ll tag you every time. Cite my sources.

Laura Burkhauser: Yeah. And I think eventually where you’ll get to—and probably, as a founder, you might already be there. But it’s like, okay, you can make kind of content about whatever you care about ,and sometimes I can’t help that. I’ll just make content about whatever’s on my mind. But ideally what you’re doing is, like, when you go into—and you talk to funders, or you go and you talk to, like, potential people that you’ve been trying to hire, you probably know the ways that they misunderstand your space or the ways where, like, they think one thing is true about your space or about kind of the way that things are going, but you think another thing is true.

And out of this, you kind of, like, create your manifesto. Like, this is what I think the space looks like. This is what I think the problems are. And this is why I think my product is an amazing kind of solution. And this is why I think you should work for me, or this is why I think you should fund me, or this is why, you know, I’m really excited to build this as our next road map. Right?

And then, if you start there, with that core set of beliefs, that helps you then understand, like, okay, this is my press story, right? This is what I would brief my PR person with. Like, I wanna make this the story that I read and—you know, in the Times or whatever.

But instead of that, it’s gonna be, like, great, this is my content lane. The four sub-hypotheses of the things that I believe about this space right now are, one, people need to make more video than ever, ever. Great. Like, that’s a content lane that someone in Descript or something should be out there saying, because I think it’s true, and because we need to start having that conversation.

So I’d say that’s, like—you can kind of start to think about what are the sub- bullets of the story that I want out in the world, and how can I create a content lane around those sub-bullets.

Lauren Ipsen: Yeah. I think that’s a great point. My CEO is incredibly high on, you know, we have to be pushing content. We have to be owning distribution lanes. We are only eight people at a VC firm that I think the general public thinks is at least 50 people, simply because of how much content we put out. But it’s all meaningful, it’s all authentic, and it’s all very specific to that individual and what makes sense for them.

And it really was something that I think coming into Decibel, for me, was, you know, thinking about what are the things that I’m passionate about? Where do I find comfort and a natural part of my personality that I think will allow me to excel here? And then what are the types of things that I actually think people care about?

And It’s a hard thing to find, but I think once you figure out, oh, these are— these are easy things for me to be able to create, they’re repeatable, and I do think people care, then it’s like you’re kind of set.

One of our investment partners started off by creating a Substack where she was really trying to focus on, you know, what people wanted to hear, and create things that she felt were kind of right down the center of the fairway. Was using ChatGPT a lot, and ultimately was not getting much of a response. And our CEO said, “Throw it all out the window and start talking like you talk to us.” Like, that’s what people want to hear, right?

Laura Burkhauser: Yes.

Lauren Ipsen: So she took that to a completely different extreme. And, I mean, she’ll reference a quote from someone and have it highlighted with a star, and it’s very glamorous and extra and fun and engaging. And there’s memes in it. And it’s—it breaks down so much of the content that people are already seeing all day long into something that’s really fun and the way we communicate about it on the backend in a lighthearted way.

Laura Burkhauser: Yeah.

Lauren Ipsen: And it has blown up. Like, people are loving it because she’s being authentic to her. She’s thrown what she thought she was supposed to do out the window and just taken on this lane that she feels is how she communicates to her husband about it or her friends. Right. So, it’s fun.

Laura Burkhauser: That’s great. Yeah. No, totally. I think that there is going to be this deluge of AI slop or people who think, like, oh, I’ve solved it. I can finally be a creator because I can just have AI generate all of the content. And I’ll just like, you know, say that content. And I’ll say, like, I am not bullish on that succeeding.

Now, what I’m not saying is that I’m not bullish on AI-assisted workflows. Hell, yes. AI-assisted workflows are an unlock. But there are things you can replace with AI. And I think I’m,even—someone showed me yesterday, like, an AI influencer that they’re making where they’ve clearly lovingly crafted every detail of this AI influencer’s personality, such that they’re almost real. And I’m like, that’s cool. That’s, like, a real creation, you know, that you’re—that you’re making.

So, but it’s, like, that’s high-effort AI, where someone’s really thought about it. And then I think there’s just ,like, when you are doing, yeah, I’m trying to appeal to everyone. I’m not gonna say anything controversial, and I’m just gonna have AI do all of the writing—it’s like, that’s a great way to be done, but it’s not a great way to build passionate kind of followers who go out and retweet you and say, “You’ve gotta read this person’s perspective.”

Lauren Ipsen: Yeah. It’s more of checking a box, doing it to do it, rather than putting something out there that actually comes with thought and empath and an understanding for what people actually want to read or see. Right?

Laura Burkhauser: Yeah.

Lauren Ipsen: Yeah, I’m right there with you. But I think it’s an interesting

process that we’ve all had to go through.

And maybe I’ll share this in the Substack too, but, basically, we all created a Venn diagram before we joined Decibel. And it’s—the exact pillars, I’ll have to go back and reference, but it comes back to, you know, who you are as a person, your specific passions, and then the craft that you want to continue to master or teach, and where they all intersect is kind of where your lane is, essentially.

And so, I think it’s an interesting thing for people to take a look at and be introspective about. Before, I mean, I initially started, I was going to just create a Substack and have it be kind of like my own monologue on different things that were happening. And I just realized that’s just not who I am. I like to yap.

Laura Burkhauser: Yeah. Totally.

Lauren Ipsen: I like to talk, and I like to chat through topics. And, you know, I think writing’s fun, but not to the extent where there’s—I mean, there’s other people that I think are better suited to put out great writing content. And I think for me, I really just like engaging with human beings. So why was I trying to do anything other than that?

So, yeah, I just think it takes a bit and a couple course corrections, and then you kind of figure out, oh, this is fun, and this works for me.

Laura Burkhauser: Yeah, there are kind of two parts in there that are really important. And the first part is, like, I think that, you know, we always need to ask when we’re creating content, who is this for? And what is the value to that person? And I think one of the ways that I see people go wrong is when they start to make content, they really know what’s in it for them.

They’re like, I want people to know my brand name. I want people to buy my product. But they aren’t really asking, like, what’s in it for the person that’s listening to this for 40 minutes or whatever.

And so one of the things that I sometimes have to kind of coach people to do is, like, you know, you don’t need to mention the name of our product, Descript, over and over again. You—

Lauren Ipsen: This isn’t an ad.

Laura Burkhauser: We need to create content that’s helpful no matter what tool people are using to, like—to make video, for example. And I—and so it can’t just be like, here’s why we’re better than all of our competitors, right? It has to try to make content that’s authentically useful to an audience, not just an advertisement. And that’s the stuff that people—that people will watch.

The other thing that you said that I think is so important is, like, you’re gonna get it wrong, and you’re gonna have to—you’re talking about the other person at your work. You’re talking about yourself. The first thing that you think is your thing and how you’re gonna, like, crack in is definitely gonna be wrong. So before you buy that $3,000 camera or before you get that like Shure microphone or before you whatever, tell everyone, “I have a Substack, and thou shalt”—you know, maybe just try it out for six weeks and see if it’s feeling like this is something that I can do.

Meanwhile, you can start to build up. Like ,if you’re doing a podcast, maybe you wanna film the first three or four and have them in the can and feel like “I like this,” before you publish them and promote them and stuff like that. Otherwise, you know, when you quit a couple weeks later, it’s gonna be a little—you’re gonna be a little sheepish.

Lauren Ipsen: Yeah, and you get—you get some inbound when they haven’t heard from you in a little bit. People are like, “Where you been? You still doing it?” Yeah. I’m like, yes, yes. I have six weddings in a row. Yes, I’m doing it.

Laura Burkhauser: My gosh.

Lauren Ipsen: Okay, cool. I think that’s all super, super helpful.

Talk to me a little bit about where you found success and specifically, I think a lot of people look for some moment where something goes viral, or they feel like they get a return on the investment.

Do you feel like there’s more of an importance on the viral thing or more of an importance on just continuing to do it and be real and you?

Laura Burkhauser: This is a great question. I think that going viral is not important, especially, I mean—so maybe if you have a product where, you know, you’re start—like, you’re just starting out, and it’s like a consumer product. You really need to go viral or something.

But a lot of us are—you know, have some kind of an enterprise or B2B component to the work that we’re doing. And in that world, going viral is not important. And that’s also like—you know, I said you need to pick your channel. Think about the channel that you actually need to succeed on. Because I think a lot of us watching the AI conversation think, like, oh, if it’s not on Twitter, it’s not—I’m not part of the AI conversation.

But it’s like, it takes a very specific kind of voice to break through on Twitter. But I’m telling you, the people that are buying your product are maybe not on Twitter. They’re maybe on LinkedIn or on the internet searching for things and being referred to a YouTube video.

And so, I think it’s much more important to think strategically about your channel and then just, like, put in—be consistent in your content creation. And I guarantee everyone, if you’re like, yeah, but how will I know about the ROI? Here’s, like—here’s a guarantee I give everyone. If you start making video content, and you keep it up for, let’s say, four months, I usually say six, but, really, I think four months, where you put out a video at least once a week for four months, if you use Descript to do it, and in four months, you’re like, this has not been positive ROI for me, I will refund a hundred percent of your subscription.

That’s how confident I am that you will have the leading indicators in just a few months that this is helping you get in front of the eyeballs of people who matter. Maybe not going viral, but I’ll tell you, after I started doing a couple of these videos, the first few videos, I think, like, I got a lot of engagement from people. Like I said, they were interview videos. That actually was super helpful for recruiting.

One of my—like, this is my job recommendation. I wrote kind of an interesting job recommendation, then did a couple of videos about interviewing. And we got a lot of really qualified candidates applying, so that was really helpful there. That’s what I was trying to make happen at that point.

But since I’ve sort of shifted into this role, and I’ve been doing more talking about the space in general, I have gotten inbounds for sales. And I have gotten, you know, people just telling me like, “Hey, I’ve seen your videos. You’re at Descript, right?” And that’s how they discovered that we’re in the set of people that they might wanna be considering.

So, to me, I think it was very obvious very early that, like, I’m getting in front of people in a way that I would never have access to them, trying to find their email or something like that. And I’m pretty confident that I’m not extraordinary at this. Like, I’m pretty confident that would be most people’s experience.

Lauren Ipsen: I disagree, but yes.

So one thing you talked to a little bit was distribution lanes. And I wanna chat about that a little bit because I think it’s important. This podcast in particular, we have it out on Substack, Apple, Spotify, YouTube. And I think that helps because there’s—and then LinkedIn, of course.

But there’s moments where one catches fire and the other doesn’t. And it’s just continuing to have visibility amongst lots of different channels. Can can you talk about that a little bit and why you feel there’s an importance to putting content out there across a multitude of different distribution lanes?

Laura Burkhauser: Yeah. I think that different distribution channels hit different people. So, typically, what I would advise is—so, YouTube, for example, and things like Spotify, these are really good for long-form content where the transcript is not only available to people, but to machines that crawl the internet and try to find good content to refer to people.

And a lot of it is long-lived. So some of our most popular YouTube videos didn’t get a lot of views and likes in the first few weeks that we kind of published them. But now that they’ve been on YouTube for years, cumulatively, they’re a pretty powerful referral channel.

And it’s the same with, like, if you’re a marketer, you know that this is how blog articles work, where it’s like, you know, you publish a blog article, and it can refer traffic to your website for years, if it’s a well-written article that is useful to people, that tends to show up when people ask a question like, how do I pick out a nice camera”

And it’s like, Descript, that’s one where it’s like—there’s like, what camera should I be using? And we wrote an article a couple of years ago that people just find because it’s a very good article about what camera you should start using when you’re getting into this stuff.

And that’s an example of just generally helpful content. So, you know, we kind of know this from the SEO game, but video is a really important part of SEO and AEO too. And it’s also just a really important part of how humans access information for months and years after you publish it.

And then I think social is often the funnel into YouTube or to your longer form stuff. And so that’s why clipping is so important. And that stuff is very ephemeral. Anyone who clicks on it is gonna click on it within, like,just a few hours of you posting it, usually. You know if it’s gonna be good or not.

And so that’s why, with social, you just want to have a ton of at-bats, and you wanna try it across a bunch of different channels and just try to get people to go from your short form stuff—not to your website, not to a sale page. Especially if—I mean, unless you’re in e-commerce, really like the—you wanna go from social to long form; from long form, whether it’s long-form like reading or long- form video or audio, to just being in the consideration set.

And then it takes time for that to—you know, if I’m listening to Decibel, I may listen to one of your podcasts. And then it’s only relevant that I know who you are 18 months later. But I’m like, hey, actually, I think Lauren is just someone in this space who knows so much about this. I’m gonna refer her to someone because I know this. That’s kind of the game you’re playing.

So if you’re focused too much on going viral, you’re really thinking short-term instead of thinking about, like, the long-term fruit that’s born from this. And then being in multiple distribution channels helps you have that full funnel experience, from tiny droplet of rain in TikTok to the expanding concentric circles of forming a relationship that that creates.

Lauren Ipsen: Yeah. I mean, I completely agree. And then I think, so often, people feel like if they put content out there that doesn’t have a million views or whatever it might be, that it’s—they failed. Right? And that’s just not the case. You know, I have been putting out this content now for over a year. And it’ll be as simple as, you know, one or two new founders reaching out and saying that they found it helpful and then that being a potential investment deal, or, you know, something that we take a deeper look at. And that in itself makes it worth it.

And, also, God, I learned so much from these conversations. So if, selfishly, I’m learning, someone else has to be, right? But I think it’s just as simple as that. But I think, so often, people are measuring it based on the amount of clicks or—and then feel the need to try and do something different or have a hot take. And sometimes it doesn’t have to be that, right?

Laura Burkhauser: Yeah.

Lauren Ipsen: Any other just pieces of advice, words of wisdom for people to just get started on doing this?

Laura Burkhauser: I love—I’m obsessed with, um, Bay Area billboards. I don’t know if you like them too, but they’re just—they’re so funny to me. I wish—honestly, like, I kind of wish I would put together a TikTok channel of just me reviewing Bay Area billboards.

But, in any case, they’re always just, like, so incredible. They’re just-

Lauren Ipsen: The best.

Laura Burkhauser: I love to drive my parents home from the airport and just be like, “Guess what that company does? Guess what that company does?” So anyways, but—

Lauren Ipsen: Did you see the most—this one woman? Did you see that she put up a billboard that’s like, “Marry Lisa,” with her contact information. And it’s literally, she just is asking someone to marry her, and it’s all an advertisement around why she’s great. So it’s, like, you’re driving from the airport, and it’s like, Vanta and E2B, and all these, like—you’ve got all of these AI agents, and then it’s like, Mary Lisa.

Laura Burkhauser: Lisa, I hope it works out for you, girl. That’s incredible.

Well, I went by one—I remember Intercom had one last year, and it was supposedly written by the Intercom CEO. And it was just like, I just need you to know three things. I need them—I need people driving by to know three things.

One, we have the best chat assistant. Two, it’s powered by AI.

I forget what the three things were, but you could tell—I mean, unless it was totally artificial, my sense was that the Intercom CEO was marching around, and he’s like, going—one of my mentors told me, the more senior you get, the more your job is to just go into different rooms and say the same three things over and over again. Right?

Lauren Ipsen: Honestly, yes.

Laura Burkhauser: So my guess is if you’re a founder, you’re a CEO, you’re listening to this, what are those three things, the three things that you would put on the Intercom billboard of, like, just put these things on the billboard?

And then, there you go. That is make a video that is just you saying those three things. Make it at 90 seconds long. Or make it four minutes and use Descript to cut it down to 90 seconds. Put it on LinkedIn, and see what happens. I think that is your assignment. And if no one engages, that’s fine. Don’t delete it. Right?

Some people tell me, like, “Well, I did all of this, and I posted it, and no one liked it, so I deleted it.” And I’m like, oh my gosh. Play the long game.

Lauren Ipsen: And even if people aren’t liking it—I just saw the other day on my own Instagram, now they can show who’s viewed your profile, or the number of people that have viewed your profile. It was somewhat terrifying. It was over a hundred thousand people had viewed my profile. But, you know, I’m definitely not getting that many likes or comments on things.

So people are still seeing your content when you put it out into the ether, right?

Laura Burkhauser: Exactly. Exactly. And I promise to retweet you, you know.

Lauren Ipsen: Thank you.

Laura Burkhauser: Let me know. Gimme a little DM, and I’ll be, like— retweet this person’s stuff.

Lauren Ipsen: God bless you. What are the three things that you have been putting out over and over and over into the world as a CEO?

Laura Burkhauser: Great question. I think that they are video is eating the world, right? Video is the dominant form of communication, and all of us— CEOs, teams, companies—need to be creating a lot more video if we want to be part of the story of what’s happening in the world.

The second thing is that I think that AI—that video generation is extremely important and is going to change the way that video is created, but don’t sleep on the orchestration and application layers, right? I don’t think that video generation is going to replace recorded media.

I think, instead, we need apps where we can put all of these different models together with recorded media and with other kind of traditional forms of editing media to create a truly horizontal video solution that can be used by everyone on your team because it is both easy and because it covers every single use case, and that’s what we aspire to be.

So I’d say that is—that’s—those are my—that’s my billboard. Now, if we could just condense that into about three words.

Lauren Ipsen: I love it. And that’s where ChatGPT comes in.

Laura Burkhauser: Yes. Thank you.

Lauren Ipsen: Okay. Laura, I want to thank you so much for coming on the show. I can’t thank you enough. I think this was super insightful for our listeners, for founders getting started on this. So appreciate you taking the time to talk through content. I know it’s gonna be incredibly valuable to them.

Laura Burkhauser: Oh, my gosh. Thank you so much for having me. It’s always a pleasure to chat.

Lauren Ipsen: So much fun. And thank you all for listening to Never Too Early. More to come soon.

00:00 Introduction to Never Too Early Series
00:34 Meet Ash Devata: From Cisco to GreyNoise Intelligence
01:34 Ash's Journey: From India to Cybersecurity
03:17 Joining GreyNoise: The Decision-Making Process
07:00 Navigating CEO Challenges and Company Dynamics
12:06 Adapting from Large Corporations to Startups
16:12 Decision-Making and Collaboration with Founders
21:42 Understanding the Role of a New CEO
22:03 Building and Sustaining Relationships with Founders
23:00 Trusting Your Gut and Decision-Making
23:36 Personal Journey and Upbringing
24:13 Lessons from Family Business
26:06 Influence of Mentors and Leadership Philosophy
26:53 The Farmer Analogy and Ecosystem Management
27:54 Challenges of Remote Leadership
33:20 Adapting to Market Changes and Industry Shifts
35:23 Reflections on the CEO Role and Personal Growth
39:09 Final Thoughts and Advice for Aspiring CEOs

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

Transcript

LAUREN IPSEN: What's up, listeners? Welcome back to Never Too Early, a YouTube series focused on unconventional talent insights for founders. I'm Lauren Ipsen, Talent Partner at Decibel, and today, you're back on my Founder Therapy series.

In this series, we'll be spending time with executives that have recently taken the leap to either start their own venture-backed tech companies or jump into a CEO seat for the very first time. These are folks that are going to be sharing mistakes, common misconceptions, learnings, and a whole lot more.

So with that, I am beyond excited to welcome my guest today, Ash Devata. Ash was formerly the vice president and general manager of Cisco Zero Trust, and today is currently the CEO at GreyNoise Intelligence.

Ash, welcome to the show.

ASH DEVATA: Hi, Lauren. Oh, I'm so happy to be here. Thank you for having me.

LAUREN IPSEN: Thank you so much for joining me. I really appreciate it. And for those listening, Ash just got back from an incredible trip where he kind of disconnected from the tech world in its entirety. And then maybe an hour into him being back in San Francisco, I convinced him to do this. So thanks for doing it.

ASH DEVATA: Well, my pleasure. So at GreyNoise, where I am right now, we have a tradition of shutting down the company every summer for the July 4th weekend or the July 4th week. So I managed to squeeze an extra few days, took a vacation to Asia, and asked a few people in Asia that I was meeting on what they think about AI. And they looked at me like I’m an alien asking them alien questions, so this reminds me of kind of the bubble wheel in tech.

LAUREN IPSEN: A hundred percent. All right, so I want to start by just kind of jumping into your background, your career, and how you ultimately got into the CEO seat at GreyNoise. So maybe you can just start with informing the listeners a little bit about yourself.

ASH DEVATA: Sure. So right now, I'm the CEO of a cybersecurity startup called GreyNoise. We're in the space of threat intelligence about edge devices, and we sell that to governments. We sell that to fortune companies. We sell that to a lot of researchers. We're a relatively small company, 60 people, figuring things out, but we got good traction in the market.

LAUREN IPSEN: Mm-hmm.

ASH DEVATA: But rewind a lot. I was born in India in a small village in a family where we were growing rice and coconuts. That's my beginning. First generation graduate. Came to the US for my master's and a scholarship. Tried to work for a startup that is 10 people. Miserably failed. And then I joined a large company called EMC and then accidentally got into security. And I've been working in cybersecurity for about 15 years now.

LAUREN IPSEN: Awesome. Cool. I didn't know that about you. What an interesting start to life, and then to be here. I mean, that's—yeah. It's probably incredibly important to do what you just did then, and remind yourself of kind of where you came from and different aspects of the world.

ASH DEVATA: Yeah, yeah. You realize things from your childhood or, you know, teenage and later on that that influenced you, but you don't know that they play, actually, such a big role.

LAUREN IPSEN: Sure.

ASH DEVATA: I'll share the story later, but, you know, I was thinking about what influenced me to become a CEO. and there are aspects of my childhood and growing up, you know, that I feel played a significant role.

LAUREN IPSEN: Yeah. Cool. I love that. Talk to me a little bit about how you stumbled upon GreyNoise and ultimately what brought you there, and why you were specifically excited about taking on the CEO seat there.

I had a conversation with a good friend of mine who—she's the CEO at TIAA. And she said, it's such an interesting thing when you come in and step into a CEO seat because, essentially, you're renting. You're renting the title. And, really, someone has created this company as a founder, and it's their baby. And you're almost coming in as a stepparent, essentially. But you want to show it the same love and care that they would. But it can be—it can be really difficult.

So I'm curious, what got you to GreyNoise, and ultimately how it's been being a CEO over the course of the past two years or so?

ASH DEVATA: To continue with your friend's analogy, maybe, you know, if it's co- parenting, it's like one direction, but if you are shifting the parents, then it's a different direction. Fortunately for me, it's more of co-parenting.

You know, I was in search for my next gig, and I was mainly exploring starting a company of my own. But I knew that I needed a technical co-founder. So I was in the market looking for a technical co-founder. And in that journey, I met Andrew Morris, the founder of GreyNoise.

And I think the decision point came down to three different things. You know, one is about me and my personal journey, what I want. The second is the founder and the founder's journey and what state the founder is in. And the third is the state of the company. What does the company actually need to go to the next level, whatever the next level actually means.

So that was my framework to make the right decision. And I feel things aligned on those three. For me, I wanted to work in very interesting tech that has impact, that has a small niche where we have a chance of winning, where I can actually have impact with building the right team and culture. That's what I was after.

The founder is extremely mission oriented. You know, Andrew just—he's a high school dropout. Comes from a family that's been serving in the Army since 1818—like, seven generations, and he's the first guy to break the chain. So he's got this enormous weight on his back to serve back to the country and sort of back to the community. And the choice of the tool for him is cybersecurity.

So, interestingly, he doesn't care about revenue, ARR, metrics, delivery, features. He just wants to catch the bad guys and be the best at catching the bad guys and sell that information as intel. So I loved that maniacal focus on mission, and that's all that matters for him. And he's one of the best hackers in the world. Understands edge and perimeter really, really well. So it's kind of—I felt it's an extremely complementary skill.

And I asked him when we were dating in the initial stage, what's giving him joy, and is he having fun with his role? And he was transparent enough and said, “Absolutely no.” Like he was hating all the meetings he's sitting in. He doesn't care about all these aspects of planning and go-to-market, but he's missing doing the actual technical work.

LAUREN IPSEN: Yeah.

ASH DEVATA: Yeah. And then the company aspect, the company was at a phase where they got a really amazing traction. And then it's trying to figure out how do you go to the next level from product maturity, go-to-market, scaling across the world, you know, redefining the customer base, all those aspects. So I thought, like, the mix of what I want, where the founder is and where the company is, mapped pretty well for this case.

LAUREN IPSEN: A hundred percent. And it sounds like, all things considered— 'cause when I used to do CEO searches at my time at Daversa, I was—those were always really, really difficult. Usually, if you're conducting a CEO search, there's typically a little bit of hair on it for one reason or another. Maybe someone's being pushed out, or maybe they're putting up their hands and saying, “Hey, I don't think that this is the best role for me,” which it sounds like it was more of that in your situation.

But it can be really difficult to bring two parties in and have them kind of both take each other's hands and make it work. It sounds like you both have incredibly complementary skill sets. And you did have a situation where someone was saying there's probably someone better-suited to focus on the go-to-market and product vision side of things, and I just want to focus on what I love. And that's the hacking and technical side of things.

ASH DEVATA: Right.

LAUREN IPSEN: So as ideal as maybe it can be coming into a first-time CEO gig. Correct me if I'm wrong, though.

ASH DEVATA: Oh, absolutely. I feel I was fortunate to come across this unique situation because this is not a board-led search. They were not looking for a new CEO. They were actually looking for a go-to-market leader, and I'm looking for a co-founder. But the conversations led to, hey, we can actually work on this together.

And Andrew said, “Hey, if you want to join us, I'll actually make room for you because I'm no longer having fun doing the CEO game.” So it's the founder having the maturity to have the self-reflection and the humility to step down to a different role and then the courage to convince the board to say that, hey, we need to bring a new CEO. And all that worked out.

LAUREN IPSEN: Yeah. And doing what's best for the baby at the end of the day. Right? So, ultimately, what made you decide that it was worth taking the leap and worth joining and kind of owning this thing in its entirety with him?

ASH DEVATA: Yeah. So, you know, all of us have mental models. So I had a bunch of mental models on what kind of company would work out or what needs to be true for a company to work out. And when I heard about GreyNoise and all the context I was getting from Andrew, that model was challenged. And that model was eventually broken.

And the thesis I had at the time was, not having all the basic foundational elements, GreyNoise somehow got amazing traction, amazing brand, and a set of logos that are using the product in and out really, really well in the right operational framework. So it was that curiosity that initially led me into trying to understand more on, wait, how did you get that customer?

We have like, you know, 20 or 25 of the Fortune 100 companies using the product, but they did not have any TRA enterprise go-to-market model. They had about 40, 50 federal government agencies, US and international, using the product, but they did not have, like, a dedicated, massive federal go-to-market, you know, approach.

So how are you able to get this amazing traction with the customers without having all these foundational elements? And you're not in a must-have product category either. So there must be something very unique I did not understand, or I don't understand, that that worked out. So that intellectual curiosity got me to understand more and more and more, and that's how we got into talking more.

LAUREN IPSEN: Cool. That's really cool. Yeah, it's so interesting. I was just talking to a friend who went through their whole job search with these parameters that she had in mind and took something completely different. And sometimes it's just a gut feeling, and at the end of the day, it's who you're working with and being excited about doing it together. And I personally believe that's the biggest thing. That's probably why I'm in the industry I'm in, but it's my strong belief, right? So.

ASH DEVATA: And another aspect is, you know, not—generally, you think of startups, you think of every startup needs to go to a billion-dollar revenue scale and have a massive exit. But sometimes you can think about, hey, maybe there are other kinds of startup where the rewards are different. It might be more mission-oriented, more impact-oriented, or you have a different level of satisfaction when you are working on a small niche segment.

So the outcome is not gonna be a billion dollar revenue, but it is gonna be a totally different kind of exit or kind of a customer base. You learn a lot in the process. So I had to—you know, I worked for Duo Security, which was acquired by Cisco, and that is in a segment where it's got a massive product-market fit.

We were selling multifactor authentication that everybody needed. Whereas, so that is the model I had. It's kind of Clayton Christensen's model of disruptive innovation. There's a bottom, massive market that is unaddressed. And if you make the solution friction-free and easy to use, you can actually start from the bottom of the pyramid, and eventually, you go up.

Whereas with GreyNoise, it's not something everybody needs. So, but people that need it value it a lot. So we're not relevant for everyone out there, but we are relevant for a small segment, and we are really, really relevant for them. So it's kind of a massive within the model there.

LAUREN IPSEN: Yeah. So how do you shift your mindset going from a Duo into a Cisco and kind of operating at this obscene scale, right? 50,000 or so employees with Cisco, is that correct?

ASH DEVATA: Oh, close to a hundred thousand. Yeah.

LAUREN IPSEN: And then you are working with a company now that's 50 people.

ASH DEVATA: Yeah. 55 people, as of today.

LAUREN IPSEN: Wow. So it feels like two different worlds, right? I think something that, you know, we're always taught to look for when we're looking for CEOs or people that have kind of had the ability to—whether it's own a business unit in its entirety or kind of a P&L, or some type of general management type of role. And then usually product strategists or product visionaries are really, you know, great to be able to naturally take on that seat.

So it's not surprising that you found your way into a CEO gig, but how crazy was it going into a company at such drastic—a drastically different scale?

ASH DEVATA: I mean, it's extremely different, that's for sure. But I was fortunate enough to see smaller companies in the past. When I joined Duo, we were about 50 people. And I got a front line seat at Duo to understand what it means to be part of 50-people company.

LAUREN IPSEN: Mm.

ASH DEVATA: Before that, I was at a 10-people company, so I had some idea. But a stable, powerful company like Cisco definitely spoils you. Think about an initiative for your product or your business unit. There is a department somewhere within Cisco that can help you. You think about expanding into Japan, there's a Japanese sales team. You want to internationalize and localize your product. There is a team that specializes in that.

So it's more about understanding how the ecosystem works and then going and building those relationships and getting work done. It's almost like working for the government or working at a large university that is, you know, well-established. You have functions, you have maturity.

With a startup, I mean, we're trying to sell in the Middle East. We're figuring out what is the right entity or the legal framework in which we need to operate. I never thought, you know, that would be a problem we need to figure out because, you know, at Cisco you had teams and teams that helped you on those.

LAUREN IPSEN: Right, right. So talk about that a little bit. So how do you now navigate not having the resources that you did, not having massive teams? What's your first kind of go-to when you're entering new territory that just feels completely unknown, and everyone's looking to you as the CEO to tell them where to go and how to go about doing it?

ASH DEVATA: You act like you have answers. People feel confident. I mean, one of the best things working for large companies like Cisco is you understand how the system works. Again, it doesn't come for granted. But if you are in a large company, and you are curious enough to understand how the system works, you spend cycles in figuring that out.

You know, you can write your notes, you can talk with people, and people are generally, like, open to share. So if you have that curiosity, you form your framework. So, no, this is how business operates. If you wanna work with the governments in the Middle East, as an example.

So I did that a lot when I was at EMC back in the day, my first large enterprise I worked with, and then at RSA, and then Cisco. So I had some mental models. So I think that is helping me a lot.

LAUREN IPSEN: Yeah.

ASH DEVATA: You know, for example, we're trying to expand into a specific segment. We're trying to build a new product. So those things don't scare me as much now because I'm like, oh, I know how this is done. I've seen this work get operationalized in big companies. So my advice to people if you're at large companies is take advantage of the machinery that operates there. You know, that was not given. Somebody built it. And there's so much you can learn just by observing how the system works there.

LAUREN IPSEN: Totally, totally. We touched on this a little bit, but I want to talk a little bit more about you're taking on a CEO role, and there's a founder who's built a lot of this from zero to one, what it then looks like from a decision-making perspective and how you collaborate, but also determine at the end of the day who kind of makes the calls. So, try and walk me through what that looks like on a day-to-day basis.

ASH DEVATA: So when I first joined GreyNoise, we talked about it because a lot of people advised me that, hey, this is going to be an area of potential friction.

LAUREN IPSEN: Right.

ASH DEVATA: So Andrew and I sat together. We wrote kind of rules of engagement. But the reality is that did not work out. Yeah. Theoretically thinking about, hey, there's gonna be

this conflict area in the future. How will we resolve it? Of course, you're gonna write, like, really cool things. But when the actual time comes—

LAUREN IPSEN: When we're purchased for $50 billion, right?

ASH DEVATA: Yeah, or people changes. Like, for example, we both talked about, hey, if I make a decision about a people change, and you personally know that person, you know, they reach out to you and you say you veto my decision, how do we deal with that situation? So we talked about those things. And unfortunately, a situation like that came into reality like four months after I joined.

We were trying to make some people changes. And Andrew and I agreed on what changes need to be made. And I told him, like, let's sit on it for a couple of days before we announce and execute on this. And next day, he came back and said, “I agree with all these changes, but with these two people, can we do this other thing? Because I really enjoy working with them, and they're really cool people.” So—and that was a real situation.

So for me, the approach I took was, it's not about, no, I already made a decision, or we agreed on X. I took the approach of, okay, let's go to first principles. Forget about these people. How do we want to make decisions in the company? Do we want to hire and work with people we like, or do we want to hire and work with people that we think are right for the company at this stage?

LAUREN IPSEN: That’s tough.

ASH DEVATA: They're brilliant people, the right people, yeah. But not for this job at this stage of the company. So revisiting the first principles on how we want to make decisions, what's right for the company, that—at least, you know, Andrew's a logical guy. So that logical approach helped us win the emotions that he was, you know, dealing with at the time.

LAUREN IPSEN: Yeah.

ASH DEVATA: And at least for now, we are following the same template, that there—this happens on a—not a daily basis, but now maybe once every couple of weeks.

LAUREN IPSEN: Sure.

ASH DEVATA: It could be about a feature, a product, someone we want to hire, you know, arc structure, someone—something we wanna communicate. And the thing that is working is going back to the first principles. How do we want to make these decisions? What's right for the company? And let's talk about the why, and let the best idea win. It's not about Andrew versus Ash; it's more about what's right for the company.

LAUREN IPSEN: Yeah, I love that. Yeah. I think it's so difficult to do, especially when emotions are tied. And I've seen firsthand falling out between great partners because of the people situation. That's so heavy and so difficult, especially when you have people that have maybe followed one individual from multiple companies, and you establish these roots, and you feel a sense of, you know—I guess a sense of responsibility for their success at the company that they, you know, were brought over to.

And some of these things, yes, you're spot on. It comes back to, this has nothing to do with how they are as a person or whether or not they're great at what they do. Let's just actually be honest with ourselves. Do we think, at this stage, in this role, this is the right person? If we were going to conduct a search right now for this person, would they look like this? Right?

ASH DEVATA: I mean, in addition to that, another way—another aspect there is the size of the decision, right? It's kind of the old saying of pick the battles you want to fight. Is this decision worth this extra level of diligence? What is the impact of this? What is the resource of the decision look like? And there might be some areas where it's worth just leaving the way it is.

Or you can say, you know, this is the founder chip bucket. And mentally, you can categorize a bunch of things into the founder chip bucket, right? So you can take different models, but there's some decisions where it's consequential for the future of the company or the culture, and you want to fight or analyze those decisions really, really well.

LAUREN IPSEN: Yeah. Yeah. Cool. Awesome. What would be your advice for someone coming into a CEO seat, as a first time CEO, where there's a founder in place that maybe isn't as open-minded to changing up some of the dynamics internally or, you know, hearing you out. Because this is a very real thing that happens.

ASH DEVATA: One aspect which I wish I did more was thinking about the why.

LAUREN IPSEN: Mm-hmm.

ASH DEVATA: So why are they bringing a new CEO, and why are they bringing you as an individual? Sometimes when you're on the other side of the job search, and I know that this is a job search, you kind of—you—it's a game theory, right? So you are selling yourself, and you have that tiny fear. What if you don't get this? What does the other alternative look like? And so on.

LAUREN IPSEN: Yeah.

ASH DEVATA: But I would say be very courageous and really dig deeper into understanding the why. Why they're bringing a new CEO, and then why they're picking you. And it might be for strengths you don't think you have or you're not aware of, but they see that, or it might be something else. So you want to have more clarity in that.

LAUREN IPSEN: Yeah.

ASH DEVATA: Second aspect is the relationship with the founder. You know, a bunch of people advised me, hey, you have to build a relationship. But what I would say, it's not about building it; it's all about sustaining it. And the founder deals with a different level of stress and weight. This is their baby. They dedicated their lives. The trade-offs they made to get to

the company, to get the company to the state where it is today. You as a new CEO just don't have the context of that. So you need to come with a level of respect about all your “don't knows” that happened before you got in.

So there might be some decisions where you think, how the heck did you pick yellow for that? Right? But you have no idea what were the conditions on which yellow was picked. So you want to respect the past decisions because you don't understand. You were not there. And nurturing the relationship with the founder is an everyday process because sometimes they can go up and down because they're just feeling a different level of pressure.

And then the other aspect is, I would say, trust your gut feeling more than you would normally do. I wish I did that. You know, I was initially like, oh, this should be X, Y, Z, or this should be in a different way. But I gave it too much of patience maybe. So as a result of that, we took longer to make a certain set of decisions. In hindsight, I wish we moved faster because I had the gut feeling.

But again, who knows? If you move too fast, it might be too brittle, and you might break it. Maybe it's a balance there. Yeah.

LAUREN IPSEN: I want to come back to when you thought that you might be interpersonally well-suited to be a CEO. And you said that part of this maybe comes back to your upbringing or, you know, the—your childhood, even a little bit. So talk to me a little bit about kind of why you thought that you might be someone down the line that could be well- positioned to run a company.

ASH DEVATA: I never thought about the title called the CEO. For me, it's more about running a business. And fortunately or unfortunately, running a business was very trivial in my mind. Because I was exposed to a lot of businesspeople growing up. So my dad was a, high school dropout. He was a farmer, but he saw a lot of gaps in the farming—as in, like, you know, he had a tractor and the tractor would break all the time. To get the tractor repaired, he had to go to a city, so he would lose two days and all that.

So he saw the gap. He started an automobile servicing shop, and then a bunch of other tractor owners came in. They serviced the tractors. And they all said they want to buy one more tractor, but they don't have enough financial support to buy a second tractor.

And back in the day, it used to take, like, two to three years to get a loan from the bank. So he raised some money from a bunch of rich people and started providing leasing and financial services to people that want to buy tractors.

LAUREN IPSEN: Wow.

ASH DEVATA: And then some of these people wanted to buy tuk-tuks, the autos in India, and then wanted to buy cars. They wanted buy trucks and machinery, like heavy cranes and all that stuff. Fast-forward to a decade, we had a financial services company that was doing leasing and hire purchase, and we had half a dozen branches, and the company went for an IPO.

LAUREN IPSEN: Oh, my goodness.

ASH DEVATA: Yeah. And I was just a kid on the sidelines looking at all this happened. So.

LAUREN IPSEN: Wow.

ASH DEVATA: And so it kind of showed me that, hey, your dad, who was a high school dropout, who was just growing coconuts and rice, is able to do that. So it is relatively not trivial, but it's doable. And the thing you wanna focus on—

LAUREN IPSEN: That’s so cool.

ASH DEVATA: The thing you want to focus on is, are you solving a problem, and are you building the right ecosystem to solve the problem?

And then just a lot of patience and day-to-day discipline. That hustle is required every day. You know, not every day is gonna be great. You get punched multiple times every week, but you just get up and keep walking. So that was— that is ingrained. So I felt like anything is possible, and it's doable.

And then a second big aspect, I would say, is one of the CEOs I worked very closely with is Dug Song, the founder and CEO of Duo. At one time he did—he told me when I was talking with him that the questions I was asking and the way I was running product org was almost like a CEO because my horizon of the business is way beyond product.

So he said I cared about things that typically a product leader doesn't necessarily care about, which is about expansion strategy, go to market, CX, and finance, and culture, and HR, and so on and so forth. And I always felt like that should be the job of every leader. Like, you know, you don't own your function, you own the company, so you need to run the company in the right way.

LAUREN IPSEN: Right.

ASH DEVATA: So I think those definitely influenced me in terms of, yeah, you should run a business. You should understand the ecosystem. And going to the farming analogy, I always believed in this, you know, when you're a farmer, you actually don't grow the plant. The plant grows by itself. Your job is to understand what is the ecosystem required for the plant to grow and control all those resources—enough water, enough sunlight, enough fertilizer, and so on.

So it's all about that care of, do I understand what needs to be true for this to grow? And am I capable of providing those resources in a timely fashion? And it's not gonna work in a systematic way, but you need to understand, oh, there's too much of water, so I should not water for two days. There’s very little soil, or there’s a storm, so maybe I should put it here.

So figuring that ecosystem for me feels like a lot of fun because it keeps changing. It's different based on the market conditions, different based on the company. But you as a CEO actually don't do any work. You are more like orchestrating. I cannot play any instrument, but I'm a great orchestrator.

LAUREN IPSEN: Absolutely. And that's the job. That is the job to a T. That's really cool. And I love the analogy. That's awesome. I am curious what it's like being at a company where you probably personally know and interact with just about everyone all the time. How does that just change your perspective on how to manage people more generally and where to focus on growing and developing talent?

ASH DEVATA: I see a different view there.

LAUREN IPSEN: Sure.

ASH DEVATA: Maybe it's because of my tenure with GreyNoise, which is, you know, less than a year and a half, versus my tenure with the previous company, with Duo. Including Cisco, it was eight-plus years.

One challenge I still face every day is—I realized this about myself—I'm more of a in-person working style. That's my natural style. So I struggle whenever the communication has to be through a screen, whether that's texting, Slack, or everything else. And GreyNoise is all remote. And I'm someone that came into the game after, in the middle of the story. So half the movie was done before I got in.

You cannot go back and build a relationship. I was not there when that story was happening. And my natural style of relationship-building is not enabled here because we're all-remote company, and we cannot afford changing that model right now.

So I don't think I have the personal relationship that you expect for a small company with the founder—you know, that a founder has with every employee that I have here. So I do not have that. But if I rewind to Duo—because Duo was about 50 people when I joined, and we were scaling. I was personally involved in a lot of hiring decisions, so I think I had more personal relationships with people there because I was involved—I was involved in building the company. And again, it's eight-year tenure there.

But here, you know, I have a very tight relationship with my executive team. I have good relationship with the next level team because I do skip levels, and I meet them often. But one thing I continue to struggle with is how do you build next level relationship with people in a fully remote environment, when you as a CEO came in the middle of the story? And everyone is accepting you with a grain of salt because, you know, you are the outlier. You are the foreign body of the system.

LAUREN IPSEN: Right. How do you gain credibility?

ASH DEVATA: Yeah. Yeah. And I think it just takes time, right? You can do a splash, you can talk about every plan you have on day one, month one, but the proof is in the pudding.

Are you delivering? Are you actually changing the culture? Are we winning more because of the initiatives you started? Are you showing up? So I think all those things matter.

LAUREN IPSEN: Yeah. I remember I was running a CEO search a while back, and there was this woman that I thought was absolutely perfect for the role, and they were so excited about her. She came in, and she just—she did such a thorough evaluation of what she felt needed to be done when she came in, in the first, you know, 90 or so days.

And she called me and said, “I just don't wanna be the bad person anymore. I don't wanna be the bad guy or girl. It's just hard.” She's like, “I know what needs to happen. I can do it. It will be great once it's done. And I don't know if I have it in me.” It's just a hard role to play sometimes.

And then add in the remote component to it, right? That's really hard. I think it's possible to— the whole process of gaining credibility, I do think, takes—it's a lot slower, in my personal opinion, when it's all happening remotely. Yeah. Being side-by-side people, they just get to know you as an individual too and realize, oh, this is a good person that genuinely has the best intentions for the company or for the people here.

So you get to understand people in a different way, as opposed to, I'm entirely guilty of only talking to my direct colleagues. And I think I have a great relationship with them, but when I need to. Right? As opposed to just because, or just to have a mind meld or share things. Right? So, yeah, it's a tricky one.

ASH DEVATA: And to come to the conclusions on what changes you want to make. You know, I feel it's your first 30, 60, 90 days of the company, and you're trying to ask a bunch of people. And so what you're getting is the declared feedback from the employees, right? They're all declarative. But what you do not have is the observed feedback.

So—because you do not have enough time observing how things are working. So people are generally good at telling what they think you want to hear, especially when it's remote and you can't see the body language in the right way and whatnot. So I think—I wish people think more actively about making decisions based on observed behavior versus declared behavior.

LAUREN IPSEN: Yeah.

ASH DEVATA: Yeah. How you process—

LAUREN IPSEN: That’s a great delineation.

ASH DEVATA: Yeah.

LAUREN IPSEN: And there's some that I think it's such a fine balance because you can come in, and obviously, you want to show the board and the team that you're here, and you're ready to make great change. And all of that's great. And it has to be so finely balanced with being a sponge and just kind of taking it all in and, yeah, observing what's actually happening

and, you know, what you wanna fight for and what's maybe not worth it and all of these different things, right?

ASH DEVATA: Yep. And another aspect of that is the company's not constant. You know, the company's changing. The market conditions are changing. So it's a moving ecosystem. And, you know, I joined GreyNoise last year, and I believe the change that has been happening in the industry in the last three years is kind of unprecedented, driven by AI, and of course, all the geopolitical events happening in the cyberspace.

So it's kind of, your theses are valid for a quarter, and then the ecosystem changes, and then you come with a new insight the next quarter. So it's not that the company is constant, and you have time to dig deep. You’re like, you know, constantly thinking about what is changing with the market and what does the relevancy actually mean on a day-to-day basis.

LAUREN IPSEN: Yeah. There's a lot of people that, over the course of the past year, especially folks that were coming out of big organizations when there was all these macroeconomic shifts that were happening, decided, oh, I'd rather just build a company as opposed to, you know, going in and joining something as product officer at, you know, a company that's maybe Series B or what have you.

Because there's a lot of action that's happening that's still so early in AI and at the intersection of AI and cybersecurity. So, so many amazing execs that came from these big, big entities are now, for the first time, either in building mode as a founder or, for the first time, have done what you've done and taken on a CEO seat for an early stage company.

What do you think the most important things that maybe you've learned over the course of your time at GreyNoise have been that maybe you just—you weren't privy to, or you didn't feel like anyone gave you a heads up on, or that have been kind of new, different challenges that you hope that, you know, folks would vet before deciding to make the leap?

ASH DEVATA: I feel, you know, to constantly rewrite your job description as a CEO, who came in the middle of the story and as the company's growing. So you—so rewriting job description, meaning at a very high level, I feel the CEO's job is to make sure, number one, the company doesn't die. And, number two, the company is relevant. And, number three, the company's actually growing.

So what is your role in the market? And so on and so forth. But where you focus on? Is it people issues, technology, go-to-market, getting funding, managing the board? Like, what area do you precisely focus on might needs to change based on the state of the union and what's changing in the market on a—not a weekly basis, but at least on a monthly basis. So I wish somebody told me that, hey, proactively think about your focus areas on a monthly basis, versus, you know, you have a template. That's one.

Second is, a lot of people said, hey, CEO jobs are gonna be very, very lonely because you cannot provide all the context to any one group of stakeholders because they'll freak out. You know, you still manage with a certain tone the board. You manage your executive team in a different way. You manage the whole company employee, you know, all hands in a different way.

But I felt that is kind of a mis-advice. I trust my executive team a lot. I share a lot of context. So maybe there's a way where, if you build enough trust with the immediate executive team, the job doesn't need to be—

LAUREN IPSEN: So lonely?

ASH DEVATA: So lonely as they say it should be, or it is in general.

LAUREN IPSEN: I love that. It feels more like a partnership.

ASH DEVATA: Yeah. So, you know, you are vulnerable. You tell them, I don't know the answer. I'm scared too, you know, about the survival of this particular project. And so you have a different level of trust. So that's—I wish people told me that. Hey, proactively figure out—you don't need to be too lonely, you know, in your CEO gig.

LAUREN IPSEN: And you don't need to necessarily immediately have the answer to everything on your own. Right? I think that's a cool—that's a really great perspective.

ASH DEVATA: Yeah. Yeah. And when I was at Cisco, I was having a blast. Cisco is a phenomenal company to work for. But I felt like I was getting really comfortable. And I always believed, like, comfort and growth are diametrically opposite, so.

And I also felt it's a—you know, once you're very comfortable with a very large company for a very long time, you might not be able to operate in a small startup because the struggles are very different. You're used to a certain level of ecosystem support, right? So I was scared about the level of comfort and my future inability to work for a small startup, and that was one of the drivers for me to leave Cisco at the time.

LAUREN IPSEN: Okay.

ASH DEVATA: And it was very personal. So I would recommend people, you know, if— there's nothing wrong in working with a large company for the rest of your life, but, you know, if you're—if that's what you want to do, you should completely do that.

LAUREN IPSEN: Right.

ASH DEVATA: Do not underestimate the scale and the support a large company provides. At a small startup, you know, you have to do everything from zero to one, and survival is, like, top of mind. At Cisco, you don't think about survival every day. And—

LAUREN IPSEN: That’s true. Yeah.

ASH DEVATA: Yeah. You know, that's the last thing in your mind, right? At Cisco, I always used to think about, you got 80 gods to please. I grew up in a Hindu family. So you always think about hundreds of gods. And every god has a role. Like, there's a god for rain, there's a god for thunder.

LAUREN IPSEN: Yeah.

ASH DEVATA: So at Cisco, you have a lot of gods to please. No matter what decision you make, that decision can be vetoed by some god sitting somewhere. So you always try to understand how many gods exist. What is their intention? What do they prioritize? And how does your decision align with them?

And you don't have those kind of aspects with a startup, right? You are the decision-maker. The buck stops with you.

But, bottom line, I feel, if you ever thought about giving it a shot, you should totally try being a CEO. You know, I think about this framework of a lot of us have only 80,000 hours to work. You know, you start working when you're 25. You retire when you're 65. So if you're lucky, you got 80,000 hours to work in your life and

LAUREN IPSEN: I like that you position it that way. You get to, yeah.

ASH DEVATA: Yeah. And there's no, you know, APR on it. You know, it's not earning any interest. There's no dividends. If you're lucky, you get all the 80,000. So, you know, if you want to categorize 5,000 of the 80,000 you have—and a lot of us don't have all the 80,000 right now; you're somewhere in the middle. So, you know, just don't think too much. You can say, I'm gonna categorize 5,000 or 7,000 off that remaining 20,000 left for me to try a CEO gig. Let's see what happens.

LAUREN IPSEN: Yeah. Cool. This has been incredibly helpful. I so appreciate you taking the time. I think this is gonna be so helpful for our founders, especially first-time founders and CEOs that are jumping into the spot that you jumped into, similarly. So thank you for hopping on the show, especially right when you got back from a trip of disconnection. Welcome back to technology, Ash. I appreciate you.

ASH DEVATA: Well, the best way is to come back to technology, Lauren. And thanks for having me. This is wonderful. Enjoyed very much talking with you and, you know, sharing my tiny context I have.

LAUREN IPSEN: Awesome. Thank you so much. And for all of you tuning in, more to come on Never Too Early: Founder Therapy. We'll talk soon. Bye-bye.

00:00 Introduction and Guest Welcome
00:53 Jonathan Schneider's Background and Journey to Founding Moderne
03:24 Diving into Pricing Strategies
04:04 Multi-Year Deals: Pros and Cons
07:22 Dynamic Pricing Models and Enterprise Sales
19:26 Knowing When to Fight or Fold in Business Deals
28:08 Reflections and Advice for Founders
31:13 Lightning Round and Conclusion

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00:00 Introduction to Never Too Early Series
00:29 Meet Maria Zhang: A Journey of Excellence
00:46 Launching Polona AI: The Stealth Journey
01:45 Deep Seek and AI Advancements
04:48 Building AI Agents with Personality
12:21 The Founder Journey: Challenges and Learnings
15:38 Forming the Dream Team
18:13 Mentorship and Startup Beginnings
18:48 Building a Founding Team
21:04 Hiring for Go-to-Market Roles
26:53 Balancing Recruitment and Sales
30:42 Navigating Venture Capital
35:44 Advice for First-Time Founders
37:41 Recommended Resources for Founders

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00:00 Introduction to Never Too Early
00:20 Meet Matt Peters: From CPO to Founder
01:03 The Founder Itch: Matt's Journey
01:48 Building a Product and a Company
02:26 Early Career and Key Learnings
03:36 The Aha Moments
05:07 The Decision to Found Fixify
10:30 Challenges and Pivots in Product Development
18:22 Go-to-Market Strategies and Customer Insights
20:24 Managing Stakeholders and Investor Relations
24:49 Building a Strong Founding Team
26:05 Effective Hiring Strategies
28:16 Onboarding and Early Success
31:33 Tracking Success and Setting Goals
38:13 Reflecting on Leadership and Emotional Resilience
42:07 Conclusion and Final Thoughts

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00:00 Welcome to Never Too Early: Founder Therapy Series
00:27 Introducing Navrina Singh: From Microsoft Exec to Entrepreneur
01:11 The Journey to Founding Credo AI
03:54 Challenges and Misconceptions in AI Governance
08:58 Building a Strong Team and Company Culture
22:17 Navigating Venture Capital and Fundraising
31:00 Advice for Aspiring Founders
38:52 Speed Round and Final Thoughts

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@nevertooearly1 and subscribe  to us wherever you get your podcasts.

The conversation also covers A.Team's rigorous vetting process for high-caliber talent, differences in contractor versus full-time employee compensation, and the importance of cultural fit and regular feedback. Amy shares her perspective on when it is optimal to hire contractors, stressing function over company stage, and encourages founders to overcome traditional stigmas associated with contract work as they build agile, impact-focused teams.

00:00 Introduction to Never Too Early

00:19 Meet Amy Kim: CRO at The A.Team

02:42 Question One: What are the pros and cons of hiring contractors versus ful time employees? Amy and Lauren address the negative association that usually comes with hiring contractors as opposed to full time employees and why it shouldn’t be taken at face value.

06:31 Question Two: Do I vet contractors the same as I do full time employees? Amy talks through not only how the A.Team vets talent that they let into their contract community, but also ways to ensure that your company is also choosing the right contractor.

13:20 Question Three: What does compensation typically look like for contractors versus full time employees? Lauren talks about how contractors can often charge a premium on the front end, or actually be more expensive from a cash perspective than hiring a full time employee, but overall, are ultimately cheaper for the organization.

15:33 Question Four: When is it less optimal to engage contractors? Amy talks about how it’s actually less important to focus on the stage of the company for contractor support and more important to focus on the specialty or function.

17:25 Question Five: How do I ensure that contractors feel properly incentivized? The biggest reason contractors fail is when they are not properly incentivized or treated as a player on the field. Amy talks about the importance of frequent check-ins and aligning incentives early in the contract engagement process.

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00:00 Introduction to Never Too Early

00:19 Meet Sally Carson: Design Leader Extraordinaire

02:05 Diving into Design: Top Questions Answered

02:22 Question One: How should founders think about their first design hire? Sally and Lauren talk about when the right time to invest in design is and what investing in design looks like in the early days.

06:01 Question Two: How important is seniority for your first design hire? What’s the right level? Lauren talks about her own experience hiring designers and how she struggled to find designers for a startup that successfully balanced strategy and execution. Sally also talks through why it might make sense to avoid marquee names like Meta and Google early on.  

09:09 Question Three: Sally discusses how she personally feels that it’s important to invest in product design first, especially before finding PMF. Pouring fire on the brand component and the marketing funnel should come after.

11:02 Question 4: When is the right time to invest in user research? Sally talks about how user research has really moved away from the academic connotation it came with 15 years ago and has become far more pragmatic today. She talks about how the right person in UX can be great to hire sooner rather than later.

14:49 Question 5: Should founders be hiring Specialists early on or Generalists? Sally talks about why she feels it makes sense to introduce specialization later in a company’s growth cycle.

16:59 Sally’s Final Advice for Founders

18:51 Closing Remarks and Contact Information

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00:00 Introduction to Never Too Early

00:19 Meet Giri Srinivas

01:23 Question 1: When is the right time to hire your first PM? Giri talks about how the founder should really be playing the part of the PM, perhaps even longer than you might imagine.

05:11 Question 2: How do you determine the right seniority of your first product hire? Giri talks about how he tends to lean towards hiring a PM rather than a Head of Product until you feel that you have established PMF.

08:56 Question 3: What is the right DNA for your first Head of Product? Giri personally has a bit of a bias towards a more technical type of product leader. Here’s why.

13:16 Question 4: What is the most productive way to set up your EPD organization? Giri discusses the pros and cons of the “four musketeer model” as well as hiring a CPTO or one person to own it all.

17:14 Question 5: Do you have any other final tips for founders? Giri has a unique perspective being a multiple time founder and most recently a Chief Product Officer at a growth-stage company. He reminds founders of the importance of staying close to the product strategy and the executive leaders that you hire.

19:16 Conclusion

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00:00 Introduction to Never Too Early

00:20 Guest Introduction: Nir Polak

01:10 A Funny Anecdote from Nir's Past

02:27 Question 1:  How do you meet potential co-founders? Nir and Lauren talk through how to evaluate whether you should start a company with someone.

03:07 Question 2: Do you think it's more productive to be mostly aligned with your co-founder or have two founders with very different POVs? Nir talks about how it is important to find a co-founder who compliments you and makes you whole, but doesn’t mirror you.

08:55 Question 3: How do you determine who makes decisions? How does voting work? Can one person fire another? Nir believes in “one throat to choke,” and explains why this tends to make him a non-believer in co-founding CEOs.

10:57 Question 4: How should equity be set up? Lauren and Nir share their perspectives on how to set the cap table up for success and avoid corrections down the road.

15:43 Question 5: What are some questions you feel are important to align on before starting a business with someone? Nir talks through how evaluating a partner to go into business with is similar to evaluating a partner you want to spend your life with. He talks through the importance of aligning on values and addressing potential hurdles early.

18:59 Final Tips and Conclusion

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Transcript

LAUREN IPSEN: Welcome to Never Too Early, a YouTube series focused on unconventional talent insights for founders. I'm Lauren Ipsen, Talent Partner at Decibel. In each episode, we'll cover the top five commonly asked questions that we get from founders building their organizations for the very first time. It's never too early to learn from the best.

I'm super excited to introduce my guest today, Nir Polak. Nir was most recently the co- founder and CEO of Exabeam. He has 18 years of experience in information security, including executive experience setting company strategy, driving execution, building new products, and bringing them to market.

He is currently now a builder at WhiteRabbit, which is leading the way for building the next generation of cybersecurity companies. So he is one of the most qualified to answer the top five questions we get from founders that are looking for their co-founders for the very first time.

Welcome to the show. Thank you for joining.

NIR POLAK: Thank you. Happy to be here.

LAUREN IPSEN: I really appreciate you taking the time. I just covered your incredibly impressive professional background. Tell the listeners something fun about you, though.

NIR POLAK: Fun about me. I don't know if it's fun, but people won't know. I almost went to jail in sixth grade.

LAUREN IPSEN: Okay. Tell us more.

NIR POLAK: So it was April Fools’, and a friend of mine and I wanted to kind of do a trick on one of our teachers. We went on this class trip, and during the class trip, we forgot, or she forgot, one of the students. And he got stuck alone and needed to kind of have his parents come and pick him up. It was a whole fiasco on that.

So we, April Fools’, thought that we were going to do something funny. So we wrote a letter from the principal that literally fired her and we signed it with the principal's signature. Now, we – we’re not that stupid. So we use the sister of my friend to do that. But, long story short, police investigations. It was a lot of fun. So that was my fun story.

LAUREN IPSEN: Oh my God. That is a fun story. Where did that leave you after? How did you get out of the debacle?

NIR POLAK: Oh, we just – we came out and just said, “Hey, it's us.”

LAUREN IPSEN: Cool. That's a fun one. Thank you for sharing. I love it. Okay.

So today, Nir and I are going to chat through a couple of different components to how you should pick your co-founder, and co-founder dynamics, and the best way to ensure that you're set up for a successful marriage. It's something that comes up a lot, and so I think it'll be really beneficial for our founders to go deep on.

So I'm going to start with the questions that I get, and then hopefully towards the end, we can cover some questions that you think are helpful to align on, and we'll go from there. Does that sound like a good plan?

NIR POLAK: Sounds great.

LAUREN IPSEN: Cool. Let's start with how you can meet other potential co-founders. And once you do meet people that are interested in potentially starting something and passionate around the same area, then how you evaluate whether or not they could be a good fit for a coworker or a co-partner.

NIR POLAK: Last company I did. a company called Exabeam. we were three co-founders, one that I knew very, very well, because I hired him to our prior company. So I got a chance to work with him for, probably, I want to say, seven years prior, so we had a lot of working relationship. And – but one that we did not know, and I got reference to him through a common person.

So I didn't need to do a lot of various datings to find the co-founder. We kind of found somebody out of the gate that kind of, like, worked really well. But what do you do? You're looking first – one is you're looking to complete kind of who you are. So you're not looking for people that are like you. Okay?

You're looking for people that, you know, are going to add value in whatever lane they're running, if it's technology, if it's product, if it's research. If it's the CEO, what do they bring to the table? But what you're relying on is, you're relying on values and perspective of the world, and, you know, So you're going on dates. You just spend a lot of dates with them.

You go out and drink and you talk about life, and you talk about their childhood, and you’re just wanting to get to know them as a person. And then you do just a lot of back channel references.

So you asked, where do you find these people? So, that's an interesting question, because I did not need to go to Seek, but I'll tell you what I'm doing now for these companies that we're building is, we're looking for a typecast of people, depending for what position. And we're going to offer them a founder position in one of our ideas.

So we literally have someone like you, Lauren, that is searching for talent, and we kind of have a typecast. What are the companies, what positions, how do they look like, like, from a career trajectory. And then we start dating them, and we figure out how it goes.

LAUREN IPSEN: Yeah. Cool. I've been doing a lot of that, obviously, as I'm sure you can imagine. And it's always really interesting to see. I mean, some founders, I'll connect them with advisors or folks that we can infuse into their fold in a fractional capacity. And then over time, they start to build rapport and start to get more excited about what they're building, and then maybe lean into more of a full-time co-founder-type role.

It's such a difficult one, especially when it's one individual that came with this idea, and then someone else, where you're wanting to give them founder equity or the same incentive and energy around the long-term vision for a product. But how do you do that when you weren't the one that initially thought of it, and all of these types of things?

So it's a difficult thing to pattern match and to marry people around an idea when it was one individual's idea, I have found.

NIR POLAK: I think that people, I think, put too much, I would say, weight into the idea itself. A company is much more than an idea.

LAUREN IPSEN: Yeah.

NIR POLAK: An idea is something very thin. You know, companies change. Their strategy changes. Even when you have the idea that doing ideation, validation, validating the idea, bringing that to a strategy, to a minimal viable product, understanding how to go to market against that, there is so much to do than just an idea.

A company is a combination of a team, an opportunity, and an execution. And I think the idea is somewhere in the opportunity, but it's not – there's so much more in there.

LAUREN IPSEN: Yeah.

NIR POLAK: And I think somebody bringing the idea is great if – I don't know. My last company I did, the idea was mine because I came up with it.

But would I say that, kind of, like, my co-founders felt that the company is less theirs than mine? I don't think so. We founded it together, and we jumped on the journey together, with the ups and downs.

And the difference between an employee and a founder is a founder is not employed by the company. Maybe it is on paper, but it's their baby. It's a much bigger responsibility than just kind of, like, being an employee. And that's what you're looking for. It's not necessarily somebody that came with it. I think that people that think the idea is everything? It's just the beginning of pulling on a thread.

LAUREN IPSEN: I think that's really cool. I think that's the difficult part to vet for, right, is trying to vet for people that are going to treat your baby like their baby, right? And really adopt that baby and take on ownership as a legitimate parent, to continue to just exhaust that metaphor.

One thing you spoke to that I want to dive a little deeper on is finding individuals that can complement your skill set, so – or complete you. I have a lot of founders in our portfolio that come from companies that, they've worked together, and they immediately start hiring great people that they've worked with in the past. But then it's a lot of like-minded individuals that are working on a problem together, and so not a lot of challenging of ideals, ideas, or different perspectives.

So my question for you is: Do you feel that it's more productive to have founders that are like-minded and really aligned on all of the same things, or to have someone come in that has a very, very different perspective than the initial co-founder?

NIR POLAK: Yeah. So I think that there's an element – again, what you want to align on is, you want to align on the working behavior and your values of what you want your baby to be, and how you want the interactions to take place, and conflict resolution to take place. But conflict is healthy. You do not want kind of, like, “yes” men all to each other.

You kind of need that yin and yang. You do need to bring that different perspective and capabilities. And I think people that work with each other in the past are great, you know? Kind of like – I've seen multiple companies that that founding team is now on their third founding, kind of a third company. And it's the same founding team over and over again, and they complete each other super well. They're very different than each other, but they all respect each other.

I don't believe in just a Kumbaya. Kumbaya doesn't create a good company.

LAUREN IPSEN: Yeah. Yeah. Cool. So differing perspectives is great, but there's a difference between, you know, having different perspectives and also just being able to work together and respect each other and create synergy in a dynamic working environment, right?

Talk to me a little bit about – I mean, the equity side of things comes up often. So how do you determine who makes the decisions? How does voting work? Can one person fire another person? Let's just assume, unfortunately, because these things do happen, that in this situation, things have hit the fan, and we have to come to some resolution and determine who's going to be the driving force for the company.

NIR POLAK: So there isn't, like, one formula, but I can give guiding factors a little bit. One is, everybody has reverse vest. And it's a four-year. It's enough time to kind of build time. There is a cliff. It's a one-year cliff. It's very important, all these different things.

And, now, what we've done in our last company is we've created what's called a founder agreement, which was a document that we kind of all agreed on what would be the working relationship? Who could fire whom? How would that go? And the last company was me and another guy that knew each other very well. We had a third that we knew less. And what could happen? And, you know, would we push him out at one point? How would that look like?

So what we did is we created a way where all of us report to the board. And they don't report to me as a CEO; they report to the board, just to put comfort for people. To kind of say, okay, it's gonna be us and the investor that's gonna make a decision, yea or nay. Same way that the board has control over the CEO itself, kind of hiring and hiring the CEO.

When it comes to conflict resolution, or kind of which idea, the best idea needs to win. And that really depends on ego. And if your – one of your allies has to be no ego in order for that to work, and then accept ideas that are not yours. And say, well, that is something you're getting – you're probably right. And that needs to have a – that goes back to the values and the culture. You need people that are like-minded on that, that won't have the ego to do that.

And then in the end, as the company grows, now you're not a founding team, it is a lot on the shoulders of the CEO. It's like, you're starting to hire more executives, and they make the decision. And, you know, that's how it goes. It’s not a dictatorship, but that's – they have the responsibility.

LAUREN IPSEN: Totally an aside, but what's your perspective on co-founding CEOs?

NIR POLAK: I don't like it.

LAUREN IPSEN: Yeah, I don't either. Elaborate. Tell me more.

NIR POLAK: Look, there could be a situation where you have somebody that owns all the go-to-market side of the house, customer-facing, and somebody that owns every side, but there still needs to be one decision-making. You can have office of the CEO, but you're going to have conflicts. And if these people get along great, then great, but when they don't, you're going to have issues.

I'm a believer in one throat to choke. That's how it goes. And that's why, when things go well, it's a team win. And when things go bad, the CEO screwed up.

LAUREN IPSEN: Yeah. What have you seen is most common from an equity standpoint? Let's say it's a co-founding CTO and, you know, a founding CEO. Even split? What feels right?

NIR POLAK: Again, it's what feels right. There are two views here. There is the view that it's common split, half/half, or third, third, third, whatever that is. And there's a view that’s, look, in the end, is who's going to have much more responsibility, and kind of going to have much more burden? CEO will have more, head of Engineering will have slightly less, and then you head of research, even slightly less than that. So that's kind of how it goes.

But I am not, let's say, religious about this. But I'm also not religious about kind of like, I think, if you win together, you win together, and you're working together. I also think it's important, though, when you're doing these dates and kind of figuring out it, it is a long journey. And, as you said, you're talking about a minimum of four years together.

It's important to also meet the spouses and the families to kind of really make sure that everybody understands that this is – they're going to give their life and soul to that because that's where the equity comes into play, so.

LAUREN IPSEN: Are there any questions that you think are really important to align on? You talked about bringing in family or meeting other key stakeholders.

But talk to me a little bit about the most important things that you think founders should be aligning on from a value standpoint, questions that they should feel similarly about.

One that comes up a lot is when to sell, if we sell. Those types of things, I think, would be helpful to cover.

NIR POLAK: You're looking for people that view the world in similar ways. Well, you know, for us, it was no ego. It was super important to kind of be able to –for all the founding team, is because you just want the best ideas to win. And you need to create an environment that does that.

The second thing was with regards to open communication. So just everything is on the table all the time, and we talk about it. The third was kind of teamwork, like always kind of believing in, we're doing things together. There's no this, they, him, her, that. There's us.

And the only – what you want to do is like, when you're hiring an executive, you want to do a lot of back channels.

So you're not asking for references from a founder. That's meaningless. LAUREN IPSEN: Yeah. Yeah.

NIR POLAK: You want to go back, and you're sending a Lauren to say, hey, Lauren, I want the somebody that reported to them, somebody that was a peer of them, somebody that managed them. And then you want to know exactly how did they interact? Not at the good times – when the shit hit the fan.

What do they do? You know, what do they do in stress? How does it look like? What is your view about responsibility? What different political issues they may have faced in their career, and how do they defuse those? That's what you're trying to figure out. And you want to do like five or six of those, of different folks along the career to kind of calibrate.

LAUREN IPSEN: I totally agree. Someone talked to me about how references are like your Instagram story or your own personal reel and how you want to be perceived. And then back channels are the photos that you're tagged in that you want to untag yourself from sometimes, right? So back channels are where you really get to the core of who these people are as executives.

NIR POLAK: And what you want to do is you want to confront the feedback you received with the founder. And you want to see how do they interact once they've been confronted with this.

LAUREN IPSEN: Yeah. Cool. I think that's great. Any other final tips, learnings of founder dynamics that you think are really helpful?

NIR POLAK: A journey of a company can be very long. But selling or not selling, there's always opportunities along the way, and you want to make sure that you're aligned on them when the opportunities arise. But everybody has their span. Some people are okay from zero to one, and others from zero to ten, and others from that.

And in the beginning, the founding team is just doing the zero to one. And they may not fit later on. They might not like what they've done later on. And it's important to kind of keep that in perspective all the time. Because one's a founder, you still need to do the right thing by the company at every stage.

So you kind of need – I wouldn't call it divorce, but you kind of need to separate sometimes when the time is right.

LAUREN IPSEN: Yeah. Cool. This is all incredibly helpful. Thank you so much for joining and for sharing your insights. And I appreciate how candid you were too. I know that some of these things are not the easiest to work through. And I know it'll be super helpful for our founders to learn from your direct experiences.

So, thank you so much for joining me on the show. NIR POLAK: Thank you for having me.

LAUREN IPSEN: Lovely to have you. And thank you all for tuning in to Never Too Early. More to come soon.

00:00 Introduction to Never Too Early

00:19 Meet Yuriy Timen: Growth Expert

01:38 Question 1: How do I find my growth engine as a founder? Yuriy emphasizes the importance of exploring product-led growth, SEO, and natural virality before experimenting with paid growth levers.

06:02 Question 2: How do I vet new growth opportunities? Yuriy shares his systematic approach to vetting growth opportunities and optimizing new channels. 

09:39 Question 3: How do I balance growth and bottom line? Lauren and Yuriy talk about the importance of aligning with your board on your growth strategy.

12:25 Question 4: What are some examples of different growth tactics that may have worked for one company but not another? Yuriy talks about his personal experience working at Grammarly in the early days and shares insights on a new company he’s advising that provides real-time feedback on your Zoom conversations.

17:09 Question 5: When would you advise a founder to use a fractional growth advisor versus hiring someone in a full time growth position? Lauren and Yuriy discuss how fractional leaders can be the best way to more deeply understand who you want to hire in a full time capacity.

20:53 Conclusion and Final Thoughts.

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribeto us wherever you get your podcasts.

Transcript

LAUREN IPSEN: Welcome to Never Too Early, a YouTube series focused on unconventional talent insights for founders. I'm Lauren Ipsen, Talent Partner at Decibel. In each episode, we'll cover the top five commonly asked questions that we get from founders building their organizations for the very first time. It's never too early to learn from the best.

I'm super excited to introduce my guest today, Yuriy Timen. Yuriy was the global head of marketing and growth at Grammarly and is now a full-time growth advisor, having worked with more than 30 tech companies in the past four years, including Canva, Airtable, Whimsical, Otter AI, Oyster, Flow Health, and many, many more. He's also been an incredibly helpful growth advisor and friend to the Decibel portfolio.

So I'm very excited to welcome my guest, Yuriy, to the show. All right. Thank you for being on the show.

YURIY TIMEN: Of course. Thanks for having me.

LAUREN IPSEN: My pleasure. So I'm super excited to have you here and talk about all things growth. I just gave an overview of your incredibly impressive professional background, but it would be super helpful if you could give the listeners something fun about you.

YURIY TIMEN: Okay. So here's one that no one saw coming. I was a competitive ballroom dancer growing up, to the point where I represented the United States at the Youth World Championships held in Moscow, Russia.

LAUREN IPSEN: Oh my God!

YURIY TIMEN: That’s – yeah, let's go with that.

LAUREN IPSEN: That's incredibly fun. That's a really good one. Yeah. I don't know if you can beat that with anything else.

YURIY TIMEN: Just putting it out there. Okay.

LAUREN IPSEN: Okay, so let's talk about growth and the five most commonly asked questions that I get from founders that are scaling their organizations for the very first time. We'll start with the first question that I get, which is: How do I find my growth engine as a founder?

YURIY TIMEN: What I like to tell founders is start by figuring out which way the current is flowing or the currents – maybe every current representing a growth hypothesis or a growth channel, and try to swim with the current as opposed to against the current. So, you know, I think every founder should first start with understanding the potential that they have for growing organically, right?

Like, you can turn to paid down the line, but you have to already be generating revenue. You have to understand your LTVs. You have to understand your payback periods if you want to get paid effectively, right? And there's nothing wrong with paid. I actually come from a paid background, a performance marketing background and foundation, but always start – start with organic.

And really, there are two, I would say, or let's call it three, but really two kind of direct response, organic growth levers that you can pull. One of them is around product-led growth, like can you generate enough word of mouth, enough kind of viral loops, sharing behavior, or what's traditionally called product-led growth. And the other one is SEO. And I think that there is almost like a checklist type of exercise that you can do with figuring out if your product is a good fit for either product virality and/or for SEO.

Maybe I won't go into those checklists in this session. But I think you absolutely got to start there, because if your product has an inherent network effect or it's inherently viral – I don't know, think Spotify, for instance, right? Or Riverside, even, you know, to bring it closer to home where, okay, you have a podcast. I'm a guest. If I ever want to start my own podcast, right, there is a viral loop right there. So it should be easy for me at the end of this call – I'm sorry. At the end of this recording it should be easy for me to be like, oh, this is how I create my own account and become a podcast host myself.

So if your product lends itself naturally to virality, lean into it. Lean into it heavily, right? Because that is a rare advantage, right? I've worked with a lot of products that have tried to manufacture virality. That's very difficult to do if your product is not inherently viral. For instance, Grammarly in the early days, it wasn't an inherently viral product.

It's like, editing your writing was largely a solo pursuit. It wasn't a collaborative activity. So there wasn't an easy way to kind of, you know, build in share loops. And then SEO, you can also run through a checklist and be like, hey, the stuff that I'm building, the needs that I'm meeting, what are the keyword universes around those needs? What are people searching for?

Is there a high volume? High volume, high intent, low competition. Are there intersections of those three where I can really make a mark in building my SEO engine, SEO program. I always start with assessing that when it comes to growth engine because those are things that are – you know, paid, it's almost like – hot take alert.

But paid is like, almost anyone can force their way into it, right? Regardless, yeah, you have to have decent LTVs, but SEO compatibility, product-led growth, viral loop compatibility, that's oftentimes inherent to what you're building. So start there by seeing if there is, you know, a strong product channel fit.

LAUREN IPSEN: Cool. Awesome. As a founder, how do I vet growth opportunities, new channels, new lanes of optimization?

YURIY TIMEN: The first principle that I think applies universally is you got to take a hypothesis-driven approach. So you're going to have ideas around different growth bets that you want to take. First of all, find a way to systematically prioritize and force strength those. It's going to be part science, part art, because you're going to have to make assumptions, like, you know, common frameworks, like the ICE framework or the RICE framework, right? Standing for Reach, Impact, Certainty or Confidence, and Effort.

Do something like that. It's less important that you score every idea accurately, because you won't. You won't score with precision. But it's important that you build the muscle of just, you know, not, jumping on the newest idea or the idea that may be the most charismatic person pitch, right?

That's not how ideas should rise above other ideas that you want to test, right? So, yeah, you have a great idea, and you pitched it very eloquently. Okay, it goes in the backlog. It gets scored, right? And then the things that rise to the top and everything in that backlog needs to have a strong hypothesis tied to it. So everybody who's putting ideas in your backlog, they should be held to that standard where an idea is not an idea until you describe the underlying hypothesis on why you think it should work. Okay?

So that's a universal principle using the hypothesis-driven approach. After that, I think with a lot of growth levers or tactics where founders struggle is defining what is the minimum viable test that I need to run to know if this channel or tactic is working or not.

And that test needs to be – when I say minimal viable test, it needs to be defined not just in terms of the budget that you need to put against a given tactic or idea, but also, it needs to have a little bit of a statistical or data science approach to it, where you say, okay, how much traffic or how many leads do I need to generate to be able to measure down funnel performance and be able to say definitively, does this channel work or does it not work for me?

It's important to have your success metrics well-defined. So the channel that you're pursuing or the tactic that you're pursuing, you have to be knowledgeable about what type of maybe KPI you need to be focused on. Like, for instance, if you're focusing on driving purchases or software subscriptions, you should probably be prioritizing more bottom funnel or demand capture channels, right?

So think like SEM, or maybe some really highly relevant display. If you care about generating just more traffic or driving up awareness, then you should be looking at channels and tactics that are more conducive to that goal, right? So that may be more like upper funnel, your demand generation channels, like YouTube or influencers and the like.

LAUREN IPSEN: Cool. How do you personally advise founders to balance growth and trying new channels, and figuring out how to optimize what they've got, and then bottom line?

YURIY TIMEN: Great question. So I have my biases, like anyone, right? And they are largely informed by where I grew up, where I came of age, which is Grammarly. And Grammarly, as you very well know, given our longstanding relationship there, Grammarly was bootstrapped for the first seven years of its existence, which meant that Grammarly was profitable. That's the only way you can bootstrap a business, right, for that long.

And that became part of Grammarly's DNA, being able to balance growth with bottom line and profitability. It was not a choice. It was a necessity when you bootstrap, right? And even after Grammarly went on to raise one funding round after another, that quality of its DNA has never gone away, right?

Like, it was already built in. So that's my bias. My bias is, a company should always be trying to get to default alive as quickly as possible, right? To break even as quickly as possible and then invest in growth commensurately with its kind of margins and its profitability.

That's my bias, but I recognize that's not always the case, because sometimes, especially in nascent markets, you have to move quickly. And that means, you know, if you're focusing on profitability, you're not going to be able to win market share and you may lose to competition.

So the first thing that I do with founders when helping them strike that balance is I ask – because most of them are going to be venture-backed companies. So I always say, what is your understanding, what is your consensus with your board on how you should be approaching balancing growth? Because whatever advice I give you, I want it to be complementary to your social contract with your board on how you should be balancing the two.

And if the answer is, we don't have one, or it's unclear, or they are stumbling their way through kind of describing how their board is advising them on balancing the two, then I say, okay. I'm like, you have some work to do.

LAUREN IPSEN: Yeah.

YURIY TIMEN: Right? Go to your board. Align there first.

LAUREN IPSEN: Yeah. Cool. What are some growth tactics that you have found that have maybe worked for one early stage company, but not another? So maybe they've raised the same amount of funding, but they're – they come from different – they're in different sectors or different primary focuses. Talk to me a little bit about how you kind of work through some of that.

YURIY TIMEN: Well, you know, I'll go back to an earlier question that you asked, which is how do I figure out my kind of growth engine or growth levers? So, you know, I talked about kind of product virality and building viral loops. I talked about SEO. Well, there are some products that are going to lend themselves more naturally to those channels and not others.

I don't know – let's run through a few of them. A few of the companies that I've worked with, right? So, for instance, uh, Airtable or Canva, right? Both former clients of mine. Obviously lend themselves extremely well to, actually, both PLG motion and an SEO motion. So, on the PLG front, they both – they're both collaborative tools, right?

In the case of Canva, there is a creator of designs, there is a reviewer of designs, there is an approver of designs, right? So, collaborative. And so that's an opportunity to invite, create

different user tiers, permissions, etc., right? Airtable is similar. There are creators of bases, reviewers of bases, commenters, etc. So, again, an opportunity to build in all those viral loops.

On the SEO front, Canva, you know, people search for all type of long tail, design or graphic searches, right? I don't know, like same sex wedding invitation, Hawaii theme. You know what I mean? And that is like – and they’re – and Canva will be there with their long tail programmatic SEO page, right? So SEO worked really well.

You contrast that with an emerging category or a category creator. I don't know. Let me think of someone. Okay, I got one. There's a company I work with called Poised, which was basically like a Grammarly for audio and video communication, right? So it's kind of like, imagine we're talking here, and I have a little overlay that's giving me a real time feedback, like, hey Yuri, you're talking too much. Let Lauren talk.

LAUREN IPSEN: Oh, that would stress me out.

YURIY TIMEN: Yeah. I mean, there are some – the UI was tricky.

LAUREN IPSEN: Yeah.

YURIY TIMEN: The UX was tricky.

LAUREN IPSEN: I feel like it would tell me to, like, lower the octave of my laugh.

YURIY TIMEN: It probably would. But, no, no, no. I didn't mean it like – no, I love your laugh. I just mean, they did –

LAUREN IPSEN: We’re actually ending the episode now. I'm just kidding.

YURIY TIMEN: Yeah, yeah, yeah. They did get pretty sophisticated with tone, intonation, nonverbal cues. They would be – but anyways, that was a complete category creator. And so there wasn't as obvious of an opportunity to lean on SEO because it's like, what are people searching for?

Are people searching for a real time Zoom communication coach? No, right? So that's an example of product that didn't lend itself to the same channel.

LAUREN IPSEN: Right.

YURIY TIMEN: On the performance marketing front, it's pretty easy for me to come in. I can, in 15 minutes – if they have all their data, in 15 minutes, I can help them figure out if they should go heavy into performance marketing or not. I ask, like, five questions. Like what's the conversion rate from website visit to, you know, sign-up? What's the conversion rate from sign-up to purchase? What is your average order value on your purchase? What is

your projected LTV? What is your split between your monthly subscribers and annual subscribers?

I have a little checklist that I go through, and based on the answers, I can be like, yeah, you know what? You can find a lot of success in the following performance marketing channels. Go after them. Or it's like, hey, you know, you're not up to par on the following metrics. Bring the conversion rate up to here, get your average order value up to here. Then you can – then you should be testing performance marketing.

So there'll be some companies, some founders I work with, well, they already have the right sort of ingredients, the right inputs. And I'll say, hey, you should absolutely be leaning into paid. And there'll be others where I’ll say, no, you got work to do.

LAUREN IPSEN: Talk to me a little bit about where you feel like it makes more sense to have someone like yourself come in in a fractional or advisory capacity as opposed to having someone come in a full-time way?

YURIY TIMEN: Yeah. So I would say some of the biggest reasons you may want to bring on fractional as opposed to hiring someone full-time – okay. Number one, this is focusing on me. You want access to a certain caliber of talent that you don't think you either can recruit full-time right now or have the surrounding resources to actually make use of them.

I'll oftentimes come in doing half a day a week with a Series A company, where they wouldn't know what to do with a hundred percent of my – of me, because of how much leverage I would be trying to create. And they wouldn't have the engine resources, the design resources, the anything resources, right?

So that's one rationale for hiring fractional. You want access to a certain caliber of talent, but you just don't think that you need or can make use of the full-time equivalent of that caliber of talent. Okay?

Number two. You need – you want – you think you need somebody in a certain role, but you're not confident what is the exact profile of the person you need to hire, and you need help figuring out that profile. You bring on someone fractional like me, not only am I helping you stand up a function or take the function to the next level, I'm helping you calibrate on who you need to hire in my place as your full-time hire.

And sometimes in my case, I actually will help you make that hire, right? So it's sort of this idea of, like, I don't know – I don't know exactly who I need in this role. So if I'm a founder who never hired ahead of growth, how do I know what to look for, right?

And – okay. Three, you don't know if this competency or channel is going to work for your product. Let's take affiliate marketing, for instance, right? I think it could work. How do I test that channel effectively?

Well, I have three options to test that channel effectively. Number one, get someone on my team already today, who probably doesn't know the channel, but maybe they're tangentially related, and be like, hey, so-and-so, take a stab at this channel. Could work, but usually, if you're dealing with that kind of situation, chances are, the person you're asking is already wearing a hundred hats, and you're trying to, throw on a hundred and first hat on them, right?

LAUREN IPSEN: Yes.

YURIY TIMEN: So it may not work. Second option, go and hire full-time. Be like, okay, I think affiliates could work. We're hiring an affiliate marketing manager. You have to take the channel from zero to one. We have – okay, high-risk, right?

LAUREN IPSEN: Yeah.

YURIY TIMEN: You're going to spend a lot of time looking for this person, and you haven't even validated the channel. This is where fractional comes in. Why not hire someone who knows the affiliate channel well, who could spend a day, two days a week? You know, you're not committing to long-term employment. You don't have the same level of, I don't know, responsibility or accountability before this person. And see if they can take this channel zero to one, prove it out, and strengthen your conviction that it is indeed a long-term channel that you want to hire full-time for.

LAUREN IPSEN: Yeah. Super helpful. I think all of this is going to be incredibly beneficial to our founders, so I can't thank you enough for joining and being on the show.

YURIY TIMEN: I love talking to founders, helping founders. For every one founder I work with, there's probably ten that I'm just friends with and helping out – helping out on a kind of casual, pro bono basis.

So, you know, I invite the founders that are listening to this to reach out to me. I will do my best to respond to everyone. And hopefully, you know, maybe even spend some time with some of the folks and help them kind of unlock new horizons in their businesses.

LAUREN IPSEN: Amazing. Well, thank you so much. Thank you for joining. And thank you all for listening to Never Too Early. More to come soon.

00:00 Introduction to Never Too Early

00:20 Meet Joe Sullivan: Internet Security Expert

00:56 Joe's Personal Interests: Snowboarding at 53

02:54 Question 1: When is the right time to bring in a CISO? Joe talks about how to index on the right kind of hire for your security organization.

07:18 Question 2: How do I know if I need a CISO or someone more in the weeds like a security analyst? Joe and Lauren also talk about when it makes sense to outsource your security advice versus when it is important to have someone on the job full time.

10:34 Question 3: What are some backgrounds that make for a good CISO? Lauren and Joe talk about the evolution of this role over the years and the different types of individuals that are best suited to play the part.

12:22 Question 4: What are the most challenging things about being a CISO? Lauren also asks about where trust and safety come into the equation.

14:08 Question 5: What separates a good CISO from a great CISO? Joe talks about early learnings in his career and ways to not always feel like the person bringing bad news to the team.

19:14 Conclusion and Final Thoughts

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1  and subscribe to us wherever you get your podcasts.

00:00 Introduction to Never Too Early

00:20 Meet Dana Lawson: CTO of Netlify

01:21 Dana's Personal Side: Fun with Chickens

02:52 Top 5 Questions from Founders

03:20 Question 1: How do you measure the output or effectiveness of your organization? Dana and Lauren discuss different metrics and tools you can use to analyze how your technical organization is performing as a whole. 

05:54 Question 2: How do you know when it’s time to hire or when your current team is not doing enough? Dana shares guidelines she follows on how to scale your team thoughtfully and effectively.

08:01 Question 3: How has AI changed expectations of your team? Lauren and Dana discuss how this is the time of 5Xing your productivity in tech, not 5Xing your headcount.

12:24 Question 4: How do you determine the best structure for a given technical org? Dana talks about how to evaluate the right format for your team at given phases of growth and how to keep a pulse on what your organization needs.

15:22 Question 5: How do you know when to promote internally and when to hire externally? Dana talks about being a woman in tech and how essential it is to equal the playing field and stay true to your process and avoid biases. 

20:37 Conclusion and Final Thoughts

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit nevertooearly.substack.com

00:00 Introduction to 'Never Too Early' Series

00:20 Meet Jennifer Longnion: Seasoned People Leader

02:30 Question 1: What are the different roles an advisor can play? Lauren and Jenn discuss the different types of modern day advisor engagements and what structures work best for startups.

06:45 Question 2: What are the primary differences between an advisor, a fractional leader, an exec coach, a Board member or an EIR? Lauren and Jenn discuss when it makes sense to bring in an executive coach, versus a mentor versus a fractional leader and what a founder can expect for each of these engagements.

11:02 Question 3: How do I structure advisor compensation dependent on the type of engagement? Lauren and Jenn break down how a founder should be structuring compensation dependent on the role they are playing for the company.

14:06 Question 4: What does the role of an informal advisor look like relative to a formal advisor? Jenn pushes on the importance of flexibility as an advisor and how these roles can often be dynamic. She also talks about how to stay close to your founders to ensure they are still getting the help they need as the engagements change over time.

17:03 Question 5: When is the right time to bring on an advisor versus hiring someone full time? Jenn talks about how an advisor can be a great solution in the interim if you are not entirely sure what you might need in this function down the road.

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

Transcript

LAUREN IPSEN: Welcome to Never Too Early, a YouTube series focused on unconventional talent insights for founders. I’m Lauren Ipsen, Talent Partner at Decibel. In each episode, we’ll cover the top five commonly asked questions that we get from founders building their organizations for the very first time. It’s never too early to learn from the best.

I’m super excited to introduce my guest today, Jennifer Longnion started her career as an organizational development leader with Best Buy, Motorola, and the Coca-Cola Company. She later joined Silicon Beach darling Dollar Shave Club at its prime as chief people officer before taking on the COO title; and then, most recently, taking the role of chief impact officer at Flexport. After three decades of leading in the hot seat, Jenn now focuses on scaling multiple ventures as CEO and founder of See & Free Consulting. Her clients have anointed her the “Org Whisperer” for her ability to walk into organizations at any stage, quickly assess the landscape, and implement transformational solutions on a dime.

So, with that being said, Jenn is one of the most qualified to answer the top five commonly asked questions that we get from founders hiring advisors for the very first time.

All right, Jenn, welcome to the show!

JENN LONGNION: Hi! How are you? So good to see you.

LAUREN IPSEN: I’m doing great. So good to see you too, and wonderful to have you here. Thank you for joining.

JENN LONGNION: Of course.

LAUREN IPSEN: All right. So I just walked listeners through your incredibly impressive professional background. But it would be really helpful if you could just give the guests something about you on a personal front.

JENN LONGNION: Yeah. For sure. I guess I bizarrely asked my wife what she thought was interesting about me on the personal front, and she said, “Nothing.” We’ve been together 26 years.

LAUREN IPSEN: Okay.

JENN LONGNION: Maybe that’s the most interesting thing. But I tell people all the time, she and I are still, after all these years, the first and last one on any dance floor at any party or event.

LAUREN IPSEN: Awe.

JENN LONGNION: So if you like to dance, come find us. We’ll always be there.

LAUREN IPSEN: Okay. I love it.

JENN LONGNION: Yeah.

LAUREN IPSEN: That’s awesome. And I’m going to out you, because I know that you mentioned this to me, but you wanted to be a DJ, it sounds like.

JENN LONGNION: I did. Yes. I still do. I dream about being – not just a DJ, but a club DJ.

LAUREN IPSEN: Absolutely.

JENN LONGNION: I want—yes. It’s got to be—I want to make people happy and see them dancing and enjoying themselves. And that is my passion. And so, someday. Just—just wait. Maybe. I’ll make it happen.

LAUREN IPSEN: Yeah. I’m ready. Okay. So we’re going to talk about advisors today. Over the past couple years—and I’m sure you’ve seen this too, Jenn, especially in your own business—but there’s been such a massive uptick in not only the demand for advisors from companies, but also, I think, more full-time operators are wanting to have a portfolio of work outside of their day job. It can really help you kind of keep a pulse on what’s happening in the market, help you feel like you have a good understanding of things that are trending in industry, and just keep you sharp while continuing to be fully occupied in a role. And so, this session is going to be specifically for founders, but really focused on advisors and the different roles in which they can play.

So, with that being said, first question for you. What are the different roles an advisor can play? What is the right time to engage one? And then how do I know who the right person is?

JENN LONGNION: Yeah. Yeah. So, I mean, I think different types of advisors. There really are. And it depends on your “why” for engaging an advisor. Sometimes it’s because there’s an expertise that somebody has that you don’t have. You need to round out your understanding, especially for founders. Many of them have never been employed, much less led massive organizations or grown companies.

And so, in some cases, it’s just what’s that know-how that I don’t have and that expertise that I need to supplement my brain, build my brain a little bit about what’s out there and what’s happening. Sometimes it’s specific industry kind of network opportunities. Connecting people to financial sources of income or investments. Sometimes it’s just listening to a pitch. You want people to give you feedback, but there’s people that have been there, done that, other founders who’ve lived the cycle, and they’ve had successful transactions.

Others, it’s about kind of how do I become a leader. It’s engaging an advisor on that front, which is how do I grow my own leadership skills, my own capabilities, and kind of up my game on that front. So there’s so many different ways that people engage advisors. And I tell people, maybe to overuse your—the title of your podcast. But it is never too early to do that, right?

LAUREN IPSEN: Ah.

JENN LONGNION: I think you—yeah, as long as you’ve got that “why” for yourself about what’s important to you, what do you want to achieve, what do you want to get from that advisor, that’s the most important thing.

And then you want to build your network. I mean, a lot of these entrepreneurial ventures rely on peoples’ networks and the ability to kind of lean on other people to help join you in your conviction to start a company and make something work. And so, the more people, the better, to kind of bring on and bring into the fold to help you do that, that are truly invested in your success.

You said, “How do I choose the right one?”

LAUREN IPSEN: Yeah.

JENN LONGNION: Oftentimes, people you know, know people. So there’s that. So if you don’t have the resources, but you have people you do trust in your—what I call kitchen cabinet, your confidantes, they will likely have networks. Don’t take that for granted. You’d be surprised just how many people are connected in the networks that you have. That’s one way. So really strong referrals.

If you’re working with venture capital, or private equity, or any sort of investment firms, they typically have a very good set of resources for you to access. Professional organizations. I hear a lot of people at YPO, for instance, as an example. If you come out of Y Combinator, an accelerator like that, you may also be able to leverage those networks. But they know who’s out there, right? And that’s a good source for you to access to find out, who can help me right now? And who’s the best? And who knows their stuff? And that’s really what you want.

LAUREN IPSEN: Super helpful. Talk to me a little bit about the difference between advisors, board members, exec coaches, execs-in-residence. There’s all these different titles, and obviously, slightly different roles that each of these individuals play. So help me break that down for our founders.

JENN LONGNION: Yeah, yeah. So advisors are exactly that—people that provide advice, right? And so, that can be an informal engagement, somebody that you just say, “I need your advice, mentorship, guidance.” And it can be formal. And often, they’ll agree to some sort of number of hours or some sort of engagement where it’s like, “Call me. Phone a friend.” I’m a phone a friend advisor for a few ventures. And I try to be clear, that’s how to engage me best, is when you need something, call me. So advisors can be a wide range and can be engaged in many different ways.

The board of directors is typically a group of people who bring certain skill sets to the table. Many times with founders, I find that they have their original investors on that board of directors because they have a very vested interest on getting a return in their investment, and they’ve done it before. A lot of them have gotten companies to scale and be successful. And so, they tend to be some of the early board of directors. But they’re there to help you make sure you’ve got a good, sound strategy, business proposition, help you fill out your team. Sometimes your leadership teams help you go get that network of other folks that can help you get the venture off the ground.

And so, I tell people, “Choose wisely, because those folks will probably be with you for a little while.” But you really want those people to help you provide the governance that you need to get your venture off the ground and your business moving forward. They really are key to making that happen.

Yeah. There’s other engagements called fractional leaders. That’s something I do a lot of. Typically, these are folks that come in on a part-time basis for an unspecified amount of time. Sometimes it’s just like, “We need you.” And oftentimes can be used to plug in—I tell people all the time, “I’m plug-in executive. That’s me.”

LAUREN IPSEN: I love it.

JENN LONGNION: Where you need—yeah, where you need leadership and don’t have it. Even if I don’t have the subject matter expertise, sometimes just having somebody that can be the grownup in the room or has kind of that leadership gravitas, credibility, and experience is necessary. Sometimes you want specific subject matter expertise, right?

LAUREN IPSEN: Yeah.

JENN LONGNION: So sometimes, you want to go after that. Either way, you will scope that role appropriately and say, “This is what we need.”

You mentioned execs-in-residence. There’s also a term called entrepreneurs in residence. But either way—sometimes, strangely, I have also been an exec-in-residence, but it was in an academic setting, because a lot of times, academia bring in execs-in-residence. And it’s somebody that’s got that kind of pragmatic business experience to bring to bear in academia. But in the business world, it’s oftentimes somebody that is either an operating partner or somebody that works closely with your investment firms or your investors. And oftentimes, it’s somebody that’s got professional experience. They have scaled companies. They’ve scaled ventures. They’re known and have credibility around that, and they have influence with those investments firms.

So they’ll either be used to do due diligence, to say, “Yeah, this person’s got it. They’ve got that thing that you want to invest in or you want to coach and nurture.” Sometimes they’ll come in and mentor the senior leadership teams and help them kind of navigate the trials of early startups. But either way, you can leverage them. And oftentimes, they’re there and they’re available, and that’s exactly what they’re expected to do. They just may be serving multiple portfolio companies for that firm. And so, that’s important to know as well.

LAUREN IPSEN: You did a really good job of articulating all of those different archetypes. Talk to me—

JENN LONGNION: Thanks. Yeah.

LAUREN IPSEN: It was a loaded question. Talk to me a little bit about the differences in which all of those individuals are compensated, and what the right structure is for each of those people.

JENN LONGNION: It’s different based on the engagement and maybe even the conditions of those engagements, right? Advisors often will expect—if they’re expecting payment, they’re saying it’s formal, they’ll want that in the form of cash compensation or equity of some sort. So it might be a certain number of retained hours, for instance. I do that a lot, where I say, “I’ll be available eight hours a month, and for this amount of money.” Or sometimes I say, “Yeah, I’ll just take equity,” right? Some people don’t want the money. And the reason they don’t want the money is they want to have flexibility with their time and their commitment, right? So just be—just know that. If you go after an informal advisor, know that that’s really under their conditions, right, because they want that flexibility.

Fractional leaders typically are going to come in on a retainer basis or a contract basis. They may say, “I’ll start with the first three months, six months.” It’s going to be a hefty price because you’re paying for somebody that’s got a lot of professional experience and probably has a good income of their own they’ve already earned. And they’ve done this for other companies or are doing this for other companies. And so, you’re going to pay more than you would pay for a full-time hire in those roles, but that’s okay if you know you need that expertise immediately to help you figure out what you’re going to need in the long-term.

One thing we didn’t talk about last time was exec coaches. So that’s another area too that a lot of people will engage. And people ask me a lot about coaching. There’s different models of coaching and different methodologies of coaching. And so, some people will engage on kind of an hourly basis for a certain number of sessions. I think, oftentimes, they’ll—let’s say I’ll be here for six months or 12 months. It also depends if they’re coaching multiple people within your organization or on your exec team, and if they’re doing group coaching. Because I do, for instance, co-founder coaching, where it’s multiple folks, especially if there’s more than one founder, and they need to get alignment, and they want coaching together, because they just want to learn to work together as a team, that’s going to be more from an hourly basis. But it’s still in an hourly engagement. And I say, “You get eight sessions or 10 sessions.” But that’s how you pay your coaches.

And an exec-in-residence, it depends. They might be compensated by the investment firm sometimes, because they’re wanting to really shape where they’re focused and make sure that they’re doing what they need. It’s more of a reciprocal relationship. Sometimes they’ll want a share of your company, right, as a part of being part of your growth trajectory. And so, just figuring out, kind of, again, why they’re involved and under what circumstances, that’ll help guide you towards how to engage them and compensate them.

LAUREN IPSEN: Awesome. Okay. So we talked a little bit about this. And you mentioned that you’re an informal advisor to a couple of companies right now.

JENN LONGNION: Yeah.

LAUREN IPSEN: What are the primary differences between engaging an informal advisor and a formal advisor?

JENN LONGNION: On the informal side, oftentimes, those come to me in the form of a referral. Somebody has referred somebody to me. And it’s because I have a certain expertise area or an industry expertise that they’re wanting to tap into, because the founder is starting a company in that arena, and they just want to know, what’s—how do I navigate this? If I want to go into COG, or if I want to go into direct-to-consumer, how do I get in there? Who are those people? How do I connect with them? Because those inevitably will be their clients or their customers.

And so, you’re going after an informal advisor usually just for an initial kind of “tell me a little bit about,” right? Those are how those conversations usually start. And I will sit down with anyone, which is a problem, because I don’t always think about, “Oh, I don’t have time for this.” But I get so excited about these new ventures.

So that’s the informal side of it. Formal advising sometimes can come—like you said, that can emerge from starting as an informal advisor, where you go from “I got a question to you,” to “Would you be on our board of directors?” or “Would you be a formal advisor for me, right, on a retained basis?” But a lot of times, you want to male sure before you engage that person in a formal way, that they will give you the time and the energy that you need from them. And then be really clear what you need from them, right, in that situation.

LAUREN IPSEN: Yeah. Well, and something that I talk to a lot of folks about that are hoping to do more advisory work is that a lot of those informal conversations are ultimately what get you to be brought into the fold as a more formal advisor, right? Which is a lot of what you were just alluding to. People want to build rapport and credibility before allowing you to just have skin in the game. And, assuming that your resume is worth it, right? So I think it takes some time to build that trust.

JENN LONGNION: It does.

LAUREN IPSEN: And then those formal advisor-type engagements come to be. But I think it’s really smart for operators to just be open-minded to taking the calls. It’s going to make you sharper. It’s going to make you have a better pulse on what’s happening in market. And then it might lead to more of a formal advisory engagement or a potential board seat down the road, right? And that’s how these things happen. It’s more organic relationship-building at the start.

JENN LONGNION: It really is. It really is. And those relationships are critical, right? For everyone, both the advisor and the founder. Yeah.

LAUREN IPSEN: My final question for you is around when to bring in an advisor or someone in a fractional capacity, versus when to know to just hire someone full-time. And then if you could walk us through kind of pros and cons to both, and would it make sense to do this, that would be helpful.

JENN LONGNION: Yeah, for sure. I mean, I kind of break it down to, like, if you know—if you don’t know what you need—you know that kind of approximately, I’ve got a challenge, I’ve got an issue, I’ve got a need. But I don’t know exactly what I need. And maybe I need somebody to help inform that, right? What’s the right resource to go after? That’s an advisor. Just call and get some advice, because somebody’s probably had that need before as well, or they are the person that can solve for that. If you know what you need, but you don’t know for how long—you don’t know if you can afford it, right?

You know, it’s like, I need this expertise. I need these kind of financial, this financial analysis, or whatever the case may be. I know I need a strong CFO partner, but I’m not ready to commit to that. I don’t know exactly what the scope of that role will be over time—then that’s when you go after fractional leadership. That’s the perfect opportunity to bring in somebody for a period of time that’s just done it before. And they can tell you what you need, but they can also probably help you find who you need for the role.

If you know what you need, and you know you’re ready for that partner, that person that’s going to jump into this crazy, chaotic joyride that you’re on, and somebody that you want to build a trusted partnership with that you’re willing to share in the company’s growth with, right, because you’re about to probably give equity to that person to join you, that’s full-time hire. That’s when you bring more people onto your leadership team, and you say, “We’re in this together.”

LAUREN IPSEN: Yeah.

JENN LONGNION: But that’s when you know. And I tell people, on average—just because I don’t like to make investments in people unless I’m willing to make a commitment to them. So I say, usually, if you can see yourself 18 to 24 months from now, working with that person, right, that’s how you know it’s time to hire.

LAUREN IPSEN: Yeah.

JENN LONGNION: You need the role. You need the person. You want that talent in place. That’s how you know. And that’s how you want to bring them in.

LAUREN IPSEN: Yeah. Well, and sometimes these advisory engagements start as, really, trying to build rapport and creating a beneficial dynamic on both sides. And then over time, if you’re working with them 18 months from now, then maybe the company’s at a different stage, where they could benefit from this person in a full-time capacity. And now that individual already knows the inner workings of the business. They already have rapport and credibility. And so, they can kind of just hit the ground running in a totally different way, right?

So it can be mutually beneficial, I think, to start in that type of role if you’re not sure what you need in a full-time hire, right?

JENN LONGNION: Yes, absolutely.

LAUREN IPSEN: Well, I can’t thank you enough for coming on the show, sharing your wisdom and insights. I think this one is so incredibly topical and comes up all the time. And you are the perfect person to walk us through it. So thank you so much. And thank you all for tuning into Never Too Early. More to come soon.

In this episode of Never Too Early, host Lauren Ipsen, Talent Partner at Decibel, dives into crucial sales compensation strategies for early-stage founders. Lauren's guest, Brian Murphy, former CRO of Sigma Computing and Sales Leader at Okta, shares his perspectives on how to hire and pay your early sales team as well as properly structure and incentivize each stakeholder in your organization to get deals done.

00:00 Introduction to 'Never Too Early' Series

00:20 Meet Brian Murphy: Seasoned Sales Vet

03:48 Question 1: When do I know if I’m ready to hire a full time salesperson? Brian and Lauren talk about when it makes sense to bring a salesperson into the mix and how to set reasonable goals for that individual when it can often be a moving target.

06:46 Question 2: With deals where everyone contributed, who gets commission? Lauren and Brian tackle how in the early days, everyone should be pretty involved and hands on in getting a deal done. 

09:25 Question 3: When is the right time to move from founder-led selling to non-founder led selling? Brian talks about how there is a difference between being founder-led and founder-involved and how one is more scalable than the other.

12:07 Question 4: What kind of Sales Leader do I hire first? An AE? An SDR? A Head of Sales? Brian talks about what your first sales hires should look like and the type of support structure they will need to be set up for success.

16:51 Question 5: How do you address compensation disparities and the amount of transparency across a sales organization?. Lauren’s final question to Brian is around common discrepancies that occur between your first sales hires’ compensation and your “phase two” sales hires that come into an organization to take a business to the next level. Lauren asks Brian his process in addressing those compensation disparities and the amount of transparency that he believes should be involved.

20:25 Wrapping Up with Insights and Advice

Want more of Never Too Early? Find us on Tiktok, @nevertooearly1 and subscribe to us wherever you get your podcasts.

Transcript

LAUREN IPSEN: Welcome to Never Too Early, a YouTube series focused on unconventional talent insights for founders. I’m Lauren Ipsen, Talent Partner at Decibel. In each episode, we’ll cover the top five commonly asked questions that we get from founders building their organizations for the very first time. It’s never too early to learn from the best.

With that being said, I’m super excited to introduce my first guest today, Brian Murphy. Brian was most recently the CRO of Sigma Computing. Prior to Sigma, he worked at Identity and access management provider Okta for six years, through massive growth, in various sales leadership roles, ultimately culminating to running all of enterprise sales for the Americas. And before that, he led sales at Alpine Data Labs, which was later acquired into TIBCO; and as sales director at Adept before it was acquired into Teradata.

So with all of that being said, Brian Murphy is one of the most qualified to answer the top five questions that we get from founders compensating their sales leaders for the very first time. Brian, welcome to the show.

BRIAN MURPHY: Thank you. Thrilled to be here.

LAUREN IPSEN: I really appreciate you making the time. All right. So today, we’re going to talk a lot about compensation, specifically on the sales side of things. So I just gave a short overview of your incredibly impressive background. But on a personal front, can you tell us a little bit about yourself? Something that would be good for listeners to know about who you are?

BRIAN MURPHY: Yeah. Happy to. So I grew up in the Boston area. Still live here. Not unlike many people from the area, live here, born here, die here. Probably will move when the Patriots move, or the Red Sox, or the Bruins move, so that’s not happening. Grew up in an Irish Catholic house. I was the youngest of four. I had nine—my father was one of nine.

LAUREN IPSEN: Wow.

BRIAN MURPHY: Six of the nine, including my father, were in technology sales, so I’m full of stupid jokes. I’m able to do that because I have four kids. A lot of dad jokes. But one of them is, growing up in that environment, Thanksgiving was like a QVR or forecast meeting, but it was really uncomfortable, so. I’ve always been in and around tech sales and wanted to be in tech sales before I really knew what tech sales was, so.

LAUREN IPSEN: Awesome.

BRIAN MURPHY: A little bit of a family business for me. Outside of work, I’m pretty boring. I’m a terrible golfer. So I try to do that occasionally.

LAUREN IPSEN: I’m really bad too.

BRIAN MURPHY: Yeah. Yeah. Not well, but it’s still fun. Like working out, like traveling, and obviously, with four kids, two dogs -

LAUREN IPSEN: So you’ve got more excuses than I do, though, on the golf course, because, I mean, you can’t play for six months out of the year.

BRIAN MURPHY: No. It’s perfect. I have a built-in excuse. So when I’m terrible, I can use that excuse all the time.

LAUREN IPSEN: Yeah. So what’s mine?BRIAN MURPHY: Yeah. Well, you actually—you played in college, didn’t you?

LAUREN IPSEN: Yeah. I used to be good at one point. And so, people expect that that’ll be the case when we go out and play. But golf is not like riding a bike, you know? It’s not something that you just remain good at when you don’t play.

BRIAN MURPHY: There’s a direct correlation associated with my career in sales. You’d think that sales people play golf all the time. But there’s a correlation associated with my career in sales and my index. And as my career has involved, my index has doubled. So I used to be a six in high school, and actually, I think I’m up now to, like, a 13 or a 14, so yeah.

LAUREN IPSEN: Honestly, better for tournament play, though, you know?BRIAN MURPHY: Yeah. Yeah.LAUREN IPSEN: You get some pops. So all good stuff.BRIAN MURPHY: Exactly. Exactly. Yeah.

LAUREN IPSEN: Okay. Okay, cool. So let’s dive into sales, and specifically, let’s dive into compensation.

BRIAN MURPHY: Sure.

LAUREN IPSEN: I thought that you would be a great person to help me work through some of this. So every founder asks me, “I think I’m ready for a salesperson. But when do I really know if I’m ready?” And how do we set goals for someone when there’s really no predictability? So especially in the early days, how do I determine quota, ramp, OTE, when it’s all kind of a moving target, in a sense? So let’s start there.

BRIAN MURPHY: Yeah. Absolutely. I think the first thing—you said it really well, Lauren—is that it is a moving target. And you have to understand there’s going to be some fluid aspects of this, right, based on the situation. So to answer the first question, when do you need a salesperson, founders should always be, I think, in the early stages, be involved in the sales process. But when you have some hypothesis associated with what your product-market fit, value proposition, and what your ICP is—and I’ll use that word “hypothesis” very specifically—you have an idea, but you don’t have that figured out. And that is such an important thing to be able to scale out an organization. When you have that direction, you need to have someone to go figure that out. It is absolutely instrumental to the company. You’re never going to be able to grow a business if you don’t know what those things are, where the focus is, the product-market fit, and the ideal customer fit, or ideal customer profile. So at that given point in time, you should have that.

As far as setting targets for individuals, I think it’s always important, but it is crucial in the early days of the organization that you set targets that that individual and the team is going to be able to hit. And that’s in the early days, and that’s continuously through. There’s nothing that’s more challenging when you have—you’re saying you’ve got the sales person in and they’re not making their quota, and then we’re going to hire more. It’s going to be really hard to recruit individuals based on that.

But I would also kind of err on the side of things that are outside of—in the early stages, outside of typical, as you would expect, revenue targets. And that could be customer meetings or feedback or numbers, some kind of leading indicators that lead to those things. Knowing, to my earlier point, that’s fluid. You don’t have everything figured out. And it’s really about kind of understanding, learning, failing fast, and adapting on those things. So again, to reiterate, when you—I think you should really focus on hiring a salesperson is when you have the hypothesis, but it’s not fully baked, right? Where that ICP and product market fit is. And align the goals very much on formalizing and solidifying those things so you can build some repeatability and predictability, because you don’t have that today.

LAUREN IPSEN: Yeah. Awesome. Cool. I think that was comprehensive and will be super helpful to our founders. You touched on this a little bit, and I’m going to ask you to take it one step further. But you mentioned how in the early days, kind of everyone’s somewhat involved and hands-on in getting a deal done. And so, with deals where everyone contributes, who gets commission? And what does an effective structure look like, in your mind, between sales, marketing, and other key cross-functional leaders, to ensure that everyone’s properly incentivized?

BRIAN MURPHY: Yeah. I’m a huge believer in taking what the overall goal of the company is and aligning that to the individuals within the company. But I think about it kind of a matrix, and there’s two elements. There’s, one, accountability; and secondly, influence. So who is most accountable for the outcome associated with that goal? But do they have influence associated with that as well? So for example, in AE, if you’re looking at revenue and how much you’re going to compensate that person, right, what percentage you’re going to pay that individual on the deal, they have high influence, because no matter what, they’re quarterback. They’re the individual that’s orchestrating all of theresources, the alignment, so on and so forth.

LAUREN IPSEN: Sure.BRIAN MURPHY: They have—and they’re also—that’s their goal.LAUREN IPSEN: Right.

BRIAN MURPHY: That’s 100% the objective of that individual. The other side of it, take somebody who is in SDR, that is responsible for really the top of the funnel in getting those meetings. They have some influence associated with that revenue. But it’s not completely control over that. And accountability-wise, their job isn’t fully to close it, but it’s to contribute associated with that. So they could get an opportunity, great opportunity, and the AU, the SEC could mess up on the proof of concept or something along those lines. So you have to think about a compensation model that kind of aligns

with what their overall accountability and influence within that. And it would be a percentage of that total deal, right? It would be a smaller percentage because it’s a sales rep. So I would think about it more in that context, as far as the individuals.

LAUREN IPSEN: Yeah.

BRIAN MURPHY: But I really would say it’s the individuals that are on the front lines in go-to- market, right?

LAUREN IPSEN: Yeah.

BRIAN MURPHY: So I wouldn’t necessarily say somebody on the product, the engineering side of that. I wouldn’t say that fully aligns to it. But anyone touching the customer and part of that end-to-end sales process should get a percentage of that. Obviously, varying degrees based on what the individual does. But closely aligning with what the overall target goal is to people who are involved in that process.

LAUREN IPSEN: Yeah. It makes sense. I think this is also somewhat involved. But oftentimes, in the early days, a founder should be very involved in the sales conversations, especially for big deals. And across the board, they should be the one that can really sell their story the best.

BRIAN MURPHY: Yeah.

LAUREN IPSEN: And so, in your opinion, at what point and how does a founder transition out of the sales calls? And when is the right time to move from kind of a founder-led sell, if you will, to more of a non-founder-led sale, or someone that comes in and runs that process in its entirety?

BRIAN MURPHY: Yeah. There’s two different parts, I think, about that, actually. So when you talk about a founder-involved or founder-led, I think those are two slightly different things. I have a huge, huge amount of respect and appreciation for founders, what they go through, what they do. And I think that they very well should be involved in sales throughout later stage of the company as well. They should always have that element. I think most of them do. The ones that I’ve engaged with are incredibly passionate individuals and good in, really, a multitude of areas. They’re incredibly multifaceted in that way.

But what I would say is that the line of delineation where it’s led, right? So “involvement” and “led” are different things. And I’ll draw the analogy—I always talk about heroic sales versus methodical and process-based sales. So when you want to start transitioning to “We need to be able to scale the organization,” and you can have these amazing individuals, which founders are, be involved in that process, and they are the difference-maker associated with getting that deal or not, when you really have that kind of ICP, you have that methodology, you know what the product-market fit is, you have those things dialed in, and you have a sales process that is a playbook that you know is going to berepeatable, that’s when you really start having to not have the founder lead those things. You need to get an individual who’s a sales running sales, to start building that, refining that, and making that repeatable, so there’s not a reliance on that person all the time, right? Now, they still will be involved, like I said. But it shouldn’t be the heroic-based sale. It should be the methodical process-based sale.

So when you start building those things, when you have a repeatable process, when you know what the ICP is, when you know what the product-market fit is, that’s when you start to have to build more and remove the founder from the leading part of that sale. Ideally, as soon as possible, as soon as you find those things.

LAUREN IPSEN: Okay. So how do we think—so I guess this is another question that comes up all the time when I’m talking to our early-stage founders, usually at the seed or pre-seed stage. But they just kind of found product-market fit. They feel really good about their ICP. How do we know whether or not to bring in a founding AE, or an SDR, or a head of sales, whatever that might entail? Should that individual have support? Should they have a sales engineer? Should it just be them, and should they be able to run it all by themselves? And then I guess with that in mind, how do we then handle sales ops, post-sales, without support, if that’s the route that we decide to take?

BRIAN MURPHY: Yeah. Yeah.LAUREN IPSEN: And I know that’s a lot of questions in one. But if you can try and break that down.

BRIAN MURPHY: There is—I’ll try to break it down the best I can. And what I’d say at the beginning when you asked about compensation of a sales rep, when a lot of things aren’t predictable, it is fluid. And I think these situations are fluid as well. So I’ll break it down in a couple different ways. You asked about individuals, when to bring in head of sales, sales, AE, SE, ops, so on and so forth. And I think it’s kind of a maturity curve of how much time the individual is focused on a particular task. And when that task becomes more important, that you have to hire somebody to support it.

So an example of that, let’s just say by way of example, you hire an AE that is doing their own pipe gen, their own outbound, their sales operations, right? They’re doing it all. And when you start to realize that they don’t—they spend so much time on the deals because they’re closing deals and moving deals. There’s only so many hours in the day, right?

LAUREN IPSEN: Right.

BRIAN MURPHY: It’s like, what hours are you throwing out? And they’re not getting to that part of it because they don’t have the time to focus on that. That’s when you’re like, okay, we’re missing opportunity, and you have to hire those additional roles, right? That’s the way I kind of look at it, is when the individual is being consumed by something that is overly important and neglecting another part of the business that is going to especially feed to that, right? So if you’re not generating pipe, you’re not going to have much opportunity. So it is, again, kind of a non-answer, but it’s very fluid, based on what you see and what’s needed. But that’s how I think about structuring an org and building an org where you need those particular rules to focus, right?

And then kind of the second part of it is hiring a head of sales versus an AE. I don’t believe in hiring a head of sales until you have something that you feel, I would say, more than 50% confident that you have your kind of ICP done. And the head of sales, that’s part of their responsibility. A huge part of it is making sure that they’re constantly developing, identifying what that is, and building kind of systems to be able to get the technographic information to focus on the ICP and processes to go into pipe gen and create that opportunity. But if you’re starting from kind of flat, it’s going to be tough. You need some kind of signaling for that individual, otherwise you’re going to hire a head of sales that ends up being kind of a sales rep.

LAUREN IPSEN: Right.

BRIAN MURPHY: And it’s an overpaid role—

LAUREN IPSEN: Totally.

BRIAN MURPHY: —for that individual.

LAUREN IPSEN: Yeah. Yeah, you don’t want to be paying head of sales compensation and have someone just operating as an IC.

BRIAN MURPHY: No. No.

LAUREN IPSEN: So, it’s thinking about at what point it makes sense to have someone in there that can really be a leader. And maybe it is that all you need is just a really senior AE that can just kind of run all of it from end to end, get deals done. And then over time, some of those folks want some leadership and guidance. And so those are very—two very different things.

BRIAN MURPHY: I would say it’s the shift between “We have more to learn than we know,” versus “We still have a ton to learn, but we know enough,” right? “We know enough.”

LAUREN IPSEN: Probably that’s a great way to put it. Yeah.BRIAN MURPHY: That’s the way I would kind of frame it, right?LAUREN IPSEN: Cool.BRIAN MURPHY: Yeah.LAUREN IPSEN: Cool.BRIAN MURPHY: Hopefully that answered the question.

LAUREN IPSEN: It absolutely did. Cool. Okay. So at every level, there are different expectations around what sales compensation should look like. We just mentioned this. But we bring in a new head of sales from a tier one company who wants to bring on A+ people. And this happens all the time, where there’s this massive delta between the founding sales team and the ones that have been grinding through the ICP and trying to figure out what the buyer looks like, and all of these different components. But they’re getting paid a fraction of what, then, these new AEs are getting paid that came from this tier one group.

And so, I guess this is something that comes up often. How much transparency is involved? What is the right process to ensure that you’re doing right by the individuals that were early in building the foundation of the company, and then those that maybe are more of the shiny objects that came with that second phase from a new leader?

BRIAN MURPHY: Yeah. So, I guess, two parts to this. One, I’ll answer the question about transparency. Me personally, I don’t know if I have the right answer for this one, candidly, because I have one or two flaws. Joking. More than that. So one of them is I kind of say, a terrible analogy, but it’s like playing blackjack. You play by the book the entire time, you win some; you lose some. But if you play the odds, you’re going to win more than you lose, maybe. But you’re going to statistically be better off on that. The reason I use that terrible analogy is, transparency, there are kind of times where you can’t be fully transparent about things.

LAUREN IPSEN: Yeah.

BRIAN MURPHY: But overall, I believe in being transparent as much as you possibly can without it being something that is breaking your fiduciary responsibility to the company or in another area. So being pretty transparent about kind of bringing in new individuals and have different skill sets in different focus areas in different stages of the company, I think you should be transparent about that. I think you should say that. And there’s nothing wrong with that, by the way. The individuals in the profile that you hire in the early days, they are what I’d say typically more artists. I always use the analogy of artists and scientists, someone recently taught me. 44 years, it took me, to figure this out. But they talked about jazz and piano players. And I’m like, “I don’t understand that.”

LAUREN IPSEN: Yeah.

BRIAN MURPHY: Apparently jazz is improvised. Didn’t know that, so learned something new.

LAUREN IPSEN: Huh. Me neither. Okay.

BRIAN MURPHY: All right, great. I’m not the only one. I looked at him like, “I have no idea what you’re talking about.”

LAUREN IPSEN: You’re teaching our listeners so much. Yeah.

BRIAN MURPHY: Yeah. Yeah. So there are individuals that are artists, and they can do things that are absolutely amazing, and they’re dynamic and the first sellers. Not that they’re not all high intelligence. But they just—they can do things in a certain way, and get deals done, and get access, and build champions. But ask them how they do it, and they can’t explain it. They can’t do it. They’re just incredibly talented in that way. It’s the same way an artist can paint something, and I’d say, “How do you do that?” So it just doesn’t compute. You have it or you don’t.

LAUREN IPSEN: Yeah.

BRIAN MURPHY: And then there are scientists, who are basically saying—not that they don’t have the art gene. But what I’d say is they generally know what the signals are and what the formulas are associated with success. And, candidly, they’re going to have different quotas, and they have likely different stakes of equity in kind of ownership of the company as well.

LAUREN IPSEN: Yeah. True.

BRIAN MURPHY: So as far as communicating what different compensation is, no, I don’t think that’s really appropriate, and I don’t know if that’s entirely legal, to be honest. But being very transparent about the company, about, look, we’re bringing individuals in that are different people. This is what we believe is the right thing for the company. Here’s why. Here’s what the growth and the stage of the company is. And, candidly, some people can adapt, and they will turn into a scientist versus an artist, or move a little bit more in that direction. And some people will say, “I’m going to go to another place where my art skills are incredibly valued, and I’m really good in that area.” And there’s nothing wrong with that, right? And there’s different people that can go through different ranges. So I think being transparent about it.

LAUREN IPSEN: Okay. Amazing. I want to thank you again for joining me.

BRIAN MURPHY: Of course.

LAUREN IPSEN: Thank you so much for the wisdom, the insights. I think this is something that comes up all the time, and this is going to be really helpful for founders as they’re thinking about structuring compensation, but also just more generally how to think about building a strong and productive sales organization in the early days. So thank you so much for your time.

BRIAN MURPHY: Of course. Yeah.LAUREN IPSEN: I really do appreciate it. Yeah.BRIAN MURPHY: If anyone wants any more dad jokes, they can find me on LinkedIn.

LAUREN IPSEN: All right. We’ll leave it at that. Okay. And thank you all for tuning in to Never Too Early. More to come soon. Thanks.

What kind of marketer do I hire first? [2:48 - 4:54]

What comes first, product marketing or a demand gen? Jen and Lauren discuss how you identify the kind of marketer to hire for and when you know that you have product market fit.

What does a good product marketer look like? [5:13 - 7:27]

A great product marketer, especially in a highly technical company, can create a value proposition that resonates with the target buyer. Jen and Lauren discuss how your first “marketer” might actually not come from a marketing background at all.

When is the right time to bring in a product marketer? [7:49 - 9:17]

More often than not, the CEO and founder of an early stage business should be the best at marketing their product, so when does it make sense for a founder to bring in an outside leader? The most valuable thing a product marketer can bring you according to Jen is a new perspective and a fresh set of eyes. Jen talks about the importance of bringing in a new perspective that can see the product in a different light.

How do I evaluate the performance of my marketing organization? [9:17 - 13:50]

How does a seasoned CMO evaluate their marketing hires? Is their demand generation lead spending money in the right areas? Are we all operating off of the same data? With roles that are more qualitative, how do you determine success? These are just a few of the topics Jen addresses.

What is the biggest mistake you have made in hiring?  [16:18 - 19:35]

Jen provides some advice for founders based on hiring mistakes she has made in her career and talks about the most important character trait she looks for when evaluating talent for an early stage organization. She also describes what it means to be “GSD.”