GTM 55: Contagious B2B Messaging Mastery with Dave Gerhardt

We were going down the escalator one day and, and a group of people went seeking wisdom and we were like, what? Like, this is the, this is, this is unbelievable. And so there was just lots of little examples like that. And they kept building and then it would be like a sales rep, you know, was, hey, I, I did a demo today with Okta and the like head of marketing at Okta, like loves seeking wisdom. And we're like, whoa. Behind the scenes. It was a small group of people that were.

Slow is smooth and smooth is fast. I want to know how this insane growth actually happened.

What are you doing when no one's around, no one's looking? Are you just showing up and doing.

The minimum or are you approaching it like a pro? Be a student of the game. Back to back episodes. What is going on this week? Hello everyone, it is Scott Barker, your new host as we make the transition from the Sales Hacker Podcast to the GTM Podcast. We'll be dropping a couple bonus episodes this week. And for those who are just joining us, we have combined the Sales Hacker podcast with the GTM podcast to create one of the largest podcasts in the space. We're super excited about it and we appreciate your support. Of course we'll still be covering sales, but since sales no longer lives in a silo, we'll also be covering the entire revenue engine, so. So that includes sales, marketing, customer success, operations, enablement, product and hiring. And our promise to you is that you'll only hear real stories from real revenue operators who have helped scale some of the fastest growing companies on the planet. Later this week we'll be re airing one of the best performing episodes on the GTM pod featuring my man Lars Nielsen on how he built out this well oiled outbound business development machine over at Snowflake. And now let's get right into it and hear from the legendary David Gerhardt, former CMO at Drift and Now founder and CEO at Exit 5. All right, and action. Here we go. Super excited for this podcast. I say this maybe somewhat frequently, but there is times and episodes where I genuinely just get to catch up with an old friend. And sometimes those old friends are incredibly busy like this man is. So this gives us about 40 minutes just to catch up, see what's going on in their life and then hopefully leave you with some stories and some actionable go to market tips, tricks, strategies that you can go and implement in your own business. I am joined by the very infamous Mr. David Geart. Dave, what's up man?

Infamous man. Infamous. I'm Very infamous now. And first of all, just to clear up something, I'm not that busy. I just am very picky.

Okay, well, now I'm, now I'm, like, almost defended, maybe.

No, we're doing it. That means that, that means that I, I, I am happy to grant you some of my time. No, I love you guys. I love you guys. It's good to, it's good to. It's good to catch up. And it was fun. When Max reached out, I was like, oh, did you know I haven't talked about a lot of this stuff, and I think I couldn't think of a better. It's fun to have a conversation with somebody who actually knows you and knows some of the story. Just makes for way more of a fun conversation. So when you guys reached out, I was like, heck, yeah, this will be a fun conversation, and I'm happy to reconnect and happy to do it, man.

Totally, man. Well, we appreciate it. Our listeners appreciate it, and it has been cool, man. Like, I feel like from when I started my career, at least in, like, more the US Tech ecosystem was like, eight years ago and obviously just been watching your journey since then. We were in such close proximity at your time at Drift, and it's been, it's been cool to watch the growth and the evolution. Uh, so you mentioned something there, which I, I've noticed you do, which is, I think, a transition that a lot of, I guess, successful folks have to make at one point, and that is this idea of kind of being a yes person. Yes, I'll do this. Yes, I'll take this promotion. Yes, I'll take over this team. Yes, I'll take this new job into now you're an entrepreneur. You have your own things. You've got a family, you love playing golf, and you've had to learn this idea of like, of no and some serious time management. Walk me through how you do that.

I'm not, I'm noticing the, the both sides of that now. And so it's, this is not lost on me. So I don't want this to come off across as tone deaf, but it is really interesting. And I think that a big part of my career, and I know you're, you, you know, have had a similar type of kind of hustle and work ethic and just the culture that you were around. I did get ahead, I think, because I would say yes, and I would, you know, record 10 podcast episodes in a week and say, and, you know, do 10 sales calls with the sales team when I was VP of marketing or you know, even back to like earlier in my career like being an intern and like say yes, I will go run that errand or do that thing. And so it is funny because like then, and I've probably even written this somewhere, talked about on a podcast. Like in the early days of Drift, you know, one of the biggest big things that I talked about was how like I responded to every email and you know, had all these one on one interactions and now I'm just at a different point in my life and I actually have, I'm on like believe on the other end of the spectrum now, which is like, it's so funny like the things that got you here. Now I'm like, man, I can't respond to every message and I needed to take more time off of social media and I got you know, somebody helping me with customer support who does this. And so it's not, it's not lost on me the both sides of that. But I just think you, you, you grow and you evolve just like a business evolves and the needs of that company are going to be different. You know, the needs of a thousand person company is going to be much different than a 10 person company. And so I think I've, I've grown and learned and evolved and now I'm just much more, I'm also have a different, it's a different point in my life. I have, I have two kids. I'm at a little bit of different point now career wise and so like I can now make a decision where before it used to be like shoot, I got offered to go to this event and it's in San Diego and it's tomorrow. Like I'm getting on that plane and I'm going now I'm like, I'm not traveling for, for anything or anyone. And that's just a, that's kind of like the macro version of that.

Yeah, yeah. I was actually talking to a friend of mine about the same idea. Cristinato you may have crossed paths with him but I was telling him because he's always, he's super responsive. He's in a later stat stage of his career. But I know this guy like answers emails right away. He's like on top of it and I'm feeling a similar, I guess like pressure. There's too many LinkedIn messages, there's too many Twitter messages too, too much going on and I just can't respond to all of them. Do you get anxiety when you leave people on red, so to speak? Do you have Systems that help you. Do you have an ea? How are you managing that evolution?

No, I have no systems, I have no automation, I have no ea. I've kind of just decided to like be very, just to manage all that myself in some ways. And I know there's a lot of automation and VA people out there, but for me I found that I just, if I can't do it myself then I think I've taken on too much and my goal is to basically work for myself and have a one person company. And so it's easy to think about like well, all of a sudden if now I'm doing so many things that I need an ea, is that really helping me? Like am I spending too much time in meetings? And one of my guardrails was like, oh, I don't want to start a services business, I don't want to start an agency. And so all of a sudden if I have lots of client meetings and lots of, you know, admin looking stuff, then it's like whoa, red flag. That's this is not the business that you're trying to create. And so like I think ultimately I've been very intentional about what I'm trying to do and I'm, I'm building a 1A business where I work by myself and I can generate enough income to support my life and invest and do things that I want to do in the future beyond B2B marketing. And so like it's, that's one of the reasons why I don't h have that because I'm actively not trying to, to grow into that. And that's just at the point that I'm at. And this is different for anybody. I, I hold no judgment or have no, you know, no judgment for anybody. Some people love the business and they're always going to be starting companies and hiring people and that, you know, the work travel and work meetings and, and you know, kickoffs and off sites that gives them energy. I'm not criticizing anybody for I've just learned about myself through, throughout my life. I'm much more of the like lone wolf creator creative. I need the freedom, I need the unstructured time. I need to be able to do things my way. And I'm fortunate enough to now be able to like run my own business and be in a position to do that. But I think it just all comes back to like understanding like who, who are you? What do you want? Where do you want to spend your time? What gives you energy? And then somewhere in that Venn diagram also has to be like, and where can you generate income? Because I would love to not do any of this and just like go do yoga on the beach or play golf somewhere. But like, I still feel the need to generate, you know, income and revenue and stuff. And so I do, so I do some stuff. But I'm very intentional about like, I have a very, very much at peace with like the what am I doing? And, and where does that exist layer of this? Where, you know, the last time we talked was, it wasn't a decade ago. But I'm just going to use that as a chapter in my life. That was more in my middle, mid to late 20s, which was a much different, which was a much different time period than I'm where I'm at today in my mid to late 30s. So just a different chapter in my life. We could play this conversation in 10 years from now when my kids are in high school and college and I'm like, I started a 50 person company and I love going to the office every day and you know, I fully, you know, reserve the right to change my mind. But I think at this season in my life, this is where I'm at and where I'm, where I'm, what I'm comfortable doing.

I love that level of self awareness and self reflection to figure out what actually drives you, what motivates you. Like that's sometimes can be a, a missing piece and we just get caught up in like building, growing, building, growing, because that's what we're supposed to do.

Well, I'm gonna, I'll talk about this stuff here because it's, it's relevant to this audience and it'll be interesting. But I've actually, Max and I have texted a lot about like what I should or shouldn't be doing with Exit 5. And so I think, you know, there's one path of me that's like, this could be a, this could be a 10 person business. I could easily hire a team. Like, I, I see that path, I see how it could be a 10 to 20 million dollar a year business. But I also have sat down and kind of like outlined a bunch of things that I don't want to do right now at this point. And like, I can't, I can't get them to work. And so instead I'm not focused on making Exit 5 this big, humongous, you know, 10 to $20 million company. Not, not humongous. But to me, hiring a team of 10 people, right. I'm very intentional about, I want to stay small And I want to do it this way. And so that. That drives a lot of my decisions. But, man, this goes all the way back to like, we'll talk about company stuff later. I've realized that every marketing and sales problem inside of a company almost always stems from just like lack of clear strategy and goals. And I'm now like feeling that again. And anytime I work on something always comes back to. It's not the tactics. It's like the what are we. What are you doing and why. If I don't have that, then that's usually when. When things are way off.

Yeah. And we'll dive into that. Cause I want to unpack that a little bit because it's incredibly crucial for building teams or building your own company, but just sort of to set the table for those listeners who maybe don't have a LinkedIn profile. Have never flipped on LinkedIn. DG was the. Started as a senior marketing manager at Drift, I believe it was back in 2015. Had a great run up until 2019. Ended up as the VP of marketing. You know, was very much the face of that business, at least how I perceive and remember Drift during those years. And then left and got a CMO role at Privy and then ended up jumping back as a Chief Brand Officer for. For Drift. Again, a shorter run that time. And then, you know, you started, I think it was like consulting and advising to begin with. And then you spun up this, this community that has now taken off. And I believe it's like the number one community for B2B marketers at least again, in terms of perception and what I hear, people absolutely love it. We've got our.

That's what I write. That's because I write. I write. It's the number one community.

So that's where my perception comes from.

We're being honest.

And I gotta, I gotta shout out. Sarah Delbarello is our marketing community manager. That's one of the first things when we were onboarding her. We got her a. A membership and she's absolutely loving it. She actually shares on our Slack channel all the time, so it's been cool. But what's missing in that journey, and I guess I'll frame it differently. You grew your career tremendously quickly to the VP level. Your time at Drift, what do you attribute that to?

First of all, thank you for the testimonial for Exit 5. I joke around about it, but I'm blown away by the quality. And it makes me so happy when I hear stories from, like, actual marketers in the space who go there and get value from it. That's awesome. And I've seen Sarah in there, so man, you got the career picture better than most. You really do not. I was like, oh, you're like, oh, he left and then he went back and then he did this thing and they did consulting the community. So you, you got it all for sure. I think there's a couple things. Number one is I jumped around a lot in my career actually before joining Drift. So before Drift, I'm pretty sure I worked at five companies in six years. And a lot of those traits still are, are, you know, are from the, the software. Hello me. Which is I, I'm very impulsive and I change my mind a lot, which is a gift and a curse in some scenarios. And I think I would get inside of a company and I get bored very quickly. It's actually a miracle that I've even had Exit 5 for two years given the way that I work. And I remember at the time I was very like self conscious about that and jumping around and it's like I knew I needed to jump but I was curious. I was like worried about the long term ramifications of that. And what's funny is somebody told me like once you land at that great company, nobody's ever going to remember. And that's exactly what happened now. And I even remember like being at Drifting, David Cancel would say like, I, you know, I had, I had this bio that I wrote that was like, you know, was a PR manager here and then marketing at HubSpot and he's like, dude, just, just change your bio and just write like, Dave Geard is VP of marketing at Drift. And I was like, oh, like once I was at that company it was like nobody remembered what else happened in that, in at that point in my career. So I say that to say this, which is, I think so much of your career is built on, you know, one or two companies that you're at and it's not just about the company but it's about like where you are at that point in your career and at point in your life. And so for me it was like I was in my late twent. I had kind of jumped around a bit at a bunch of different companies and I had gotten this itch to be at a startup, but I was, I like I didn't, I was at a big company and then I didn't join the right one and I wasn't doing the right stuff. And I finally, just by luck I fell into this opportunity At Drift, where I had this podcast outside of work that was my own, called Tech in Boston, where I was going around and interviewing startup founders. And it kind of had grown a small little audience inside of Boston. We had done, like, 50 episodes, couple thousand downloads, you know, a couple thousand people on the email list. It was small, small. But David Cancel and Elias had went and they started Drift, and they were basically launching the company, and they DM'd me and said, like, you know, hey, we're having a party. We're having a launch party, like, invite to you if you want to come. Like, I was a local blogger or something, right? And I didn't go, probably because I don't like to go to things like that, but I messaged David back and I said, like, I'll cover it in my newsletter, and by the way, could I have you on my podcast? And so I ended up having him on the podcast. I go to interview him, and we. We kind of hit. We. We hit it off at the same time. They were hiring their first marketing person, and I remember I did that interview, and I. I was working at HubSpot at the time, and HubSpot's an amazing company, but for me at the time, it was not the right place. I. It was a little bit too big for me. And I met these guys at Drift, and they, like, had this startup energy, and they also had raised a bunch of money because they were proven, you know, entrepreneurs already. It just was this, like, perfect scenario. And I applied for the job, and I get an immediate message back the next day from Keith, who I love, who was doing recruiting there, and he's like, hey, sorry, we already got somebody. I was like, damn. Like, I thought this was the opportunity. Later that day, I get an email from David Cancel, who says, hey, Keith told me you. You applied. Like, come back. Let's. Let's hang out. And I was like, oh, this is amazing. Like, there's a chance here. And I'm getting energy even just retelling them this. And so I went back and I talked to him, and we. We spent a bunch of time together. I spent a bunch of time with Elias, and it was like, I was like, oh, this is going to work out. I'm going to get an offer. And I was getting married at the time, and they were like, all right, go get married. Go on your honeymoon. Like, this was like, within two weeks, right? Go get married. Go on your honeymoon. Come back and we'll revisit this and we'll make an offer. And I just remember Feeling like, man, these people are so connected in this industry. They've raised the best money from the best VCs, they have the best network. Like, I felt like I was cheating. Like, I could get this job. I was like, they. If I go away for two weeks, they're gonna hire some, you know, actual smart person. That's literally. That's how I felt, honestly. And I did something that I never. I'm not a very, like, pushy type of person when it comes to stuff like this. And I did something that I'd never done before, which is, like, kind of straight up out of, like, a startup, like, hiring book, which is like, I emailed them. Like, Keith sent me that message, and I was like, no, this. We're not. This is not what's happening. Like, I had no leverage. Also, I was like, I need an offer now. If you guys want me. Like, I need an offer now. I was like, I'm just gonna ask for it. And I guess they loved that. And I came back in. I basically, I met Re. I Elias, like, had me in a conference room for like, an hour. And I basically just like, passionately pitched, like, why you need to make me this offer. And. And they did. And. And I end up going there. So, you know, sorry to go on a rant and tell that story, but I haven't told that often. And fast forward to right place, right time. Got to grow really fast, do a lot of things. Like, I had a bunch of side projects on my own, and I kind of. I worked inside of a company, but I never got to touch all the stuff before. And so it was like this perfect point in my career where there was like, whoa, we don't have a website. Okay, Dave, figure out how to do a website. We don't have, you know, co marketing. Figure out co marketing. We've never done ads. Figure this out. And so I got to do all those things within the first year or two of the company. I got to hire some people and build a team. And so I think it was a combination of, like, the right company and me being there at the right time. That fast forward, I spent, you know, about four and a half years there. And so I was able to kind of grow as fast as the company did during that time. And then I left.

Thanks for sharing, sharing that story. And that's what this is all about. This podcast is those, you know, stories that haven't been, like, widely told. And I love the tenacity, the. The guts to just be like, listen, I need that offer now. And I feel like there is those inflection points in your career where you like looking back, I don't even know what came over me. You know, I had that with this like sales hacker role. I just like, I could see the opportunity. I was just like, I'm just gonna get this. I, I don't care, I'm just gonna make it happen. And you know, those end up having such an incredible impact. Like that little inflection point, look where it led you had you not went that hard. Do you ever think about that?

Yeah, it was, I think about it all the time. I could have easily not and I do think about where I would have been. And I, I will confess though, obviously it was a life changing experience for me. HubSpot as a company has continued to do very well. And so I do often think about, I do the math on like, well, if I had 10 years of HubSpot Stu.

That's true, that's very true.

And like I, I don't mean that in with any disrespect at all. It's just like I, you know, you just, you kind of always like weighing out both of those. But I, I think that my bet.

Is he wouldn't have lasted 10 years at HubSpot.

Oh, hell no. So it's not even a real scenario. It's not even a real scenario. No way. So that's fair. I, you know, I think the thing that I take away from that drift experience though is there was some financial gain for me from it, but a lot of it has come later in that, you know, I still, I still to this day I have companies or people reaching out to me that were like, hey, we're fans of like what you did, what the company did, like, can we hire you to do consulting? And I've had many opportunities that have come that were not directly like deposited to my bank account from that experience. And so I think it just comes back to like, you got to be able to look at your career and I didn't know this at the time, but to look at your career and think like, yeah, I might be making like X fixed number in salary, but like being around these people, like I got exposed to so much by being there. Like I got to go, you know, get on a plane and go with the two founders of this company to like, to Sequoia and hang out at Sequoia on the west coast and meet all these companies and we got, we got a 40 minute meeting just to talk with the CMO of Facebook at the time. Like things like that or to be in meetings and learn these different experiences. And so I think like I actually wrote about this recently in Exit 5, which is, I was trying to like be positive in a world where like a lot of marketers are getting laid off or there's budget cuts or like maybe the company that they're working at is like not growing as fast as they used to and they cut their budget and so it's not that fun. And I just was like, look, you got to be able to see this as a career. Like you have to be selfish and think about yourself and see all of these things as like, you know, assets that are going to help you in your career. And so maybe you're, maybe you're a marketing manager at a company right now and like they just laid off half the team and you have no idea what you're doing, but they asked you to like lead marketing for the first time, right? It's easy to be like, oh shit. But it's also like, you know what, even if I fail at this, like I'm going to spend the next 12 to 24 months like learning a hundred times more than I knew about marketing right now and, and I can go then get another job after this and I'm going to already be better. And it was like one of the fun things for me about going to Privy and changing companies was like I got to then take all the lessons that I learned the hard way at Drift both good and bad over four years and like start new and apply them to a new company. And so I think having that lens and like it doesn't, it's important I believe in like you getting the most salary and make the most money that you can make for sure and look out for yourself. But at the same time there's some intangible cost that comes from like the, the learning and the experience and being on the team. And so I think outside of the actual, you know, the day to day job, so much of this matters at like which company are you at? What are the other managers on the team look like? Who are the other VPs? What's the culture like? Is it in the right industry that's going to give you the right like playing field to be on to learn and then you can monetize those skills in different ways down the road other than just a salary that you're getting?

Couldn't, couldn't agree more. It's like, I think a lot of us, particularly in tech, we, we see our equity package and we're like ooh baby, that's going to be the big payoff. I'm going to, you know, spend my four years here and then I'm going to ride off into the sunset. Or you get a promotion, you have this bigger salary. But I've found the same thing. It's the experience, it's the story and the network that become the real wealth creation tool that no one can take from you. And that's repeatable, it's scalable. You can do it again and again and again. Once you, once, once you have those things. So I want to pull it back to something you said earlier which was most of the friction or mistakes that happen in marketing and sales. You know, we can expand that out to the whole go to market team comes from not having a clear strategy and goals. Do you have a, maybe an example of a time at Drift or Privy when first you did that right. And everyone was beating to the same drum and it just felt so easy. You crushed it. And then on the flip side, was there a time period where, you know, there was no clear strategy and goals and you end up falling on your face?

Yes. So the first one, there's this phrase Andy Raskin talks about a lot. I think it's like, I think it's him. He talks about your story is your strategy. And so at Drift in the early days it was so clear. We, we were so rallied around this idea of conversational marketing that I've never been inside of a company that was so aligned for like a 24 month stretch because there was like a category that was buzzing and growing. It was very clear who we were building for and what we were doing and why. And we were building. We, you know, we, our mission was to build the leading conversational marketing platform. And so if we launched a new video product, positioning for that product was easy because okay, it's going to be conversational video. It's all going to tie back to like how does this product help you start conversations? And so typically inside of a company when the positioning and messaging questions are harder or, or less clear and less obvious, it's because there's lots of layers on there. And so like, well, we want to be. So this is a made up example. This is not about Drift. But I'm just building on that example, right? Which is like well, we want to be conversational marketing but like, you know, we have this legacy product and then we have this other one and like we now kind of compete in this market in one of our part partners does this and so we can't say this. And then there's this one VP who wants us to target this Persona and like we have a new sales team who's focusing on this. And so then, then they're like hey marketing team like right positioning for that. And you're like this is impossible versus like at that time in the company it was early, we were just trying to get market share and bring on good fit customers. And so the positioning was very simple and easy. That made it great. Then a not example of when that change was. Eventually we hit a wall where inbound demand like we had grown basically all through word of mouth and inbound and then all of a sudden we started to reach a new point in the market where people didn't know who we are. And so we had to sell and market differently. And that was a rude awakening and that was not a change that you can make overnight. And I wish I had more foresight to have seen that coming. And like we changed the mix earlier but then the company decided to like go up market and is very hard to change who the ideal customer was when you have existing teams that have existing plans and goals that are like more focused on the old strategy. And so it's like well we still want to keep the SMB revenue because we don't want to just like our revenue to go to zero and have the board and everybody questioning what the hell we're doing. So we need to support that and we have a team of X people on there and whenever there's a team of people on there those people have performance goal, you know comp, performance based incentives goals. It's all going to be tied to that. But then the company is fundamentally going like more enterprise. That just creates a lot of internal friction and waves and mismatch incentives and people are aligned differently. And so that's, that's an example there. And then when I went to Privy at the time they had just a different sales and marketing. The two sales and marketing motions were fundamentally set up to compete with each other because the sales team for whatever reason like wouldn't. They had a self service motion and a sales motion and the sales team would not get credit for anybody that came in and came in through the website and like didn't get. I forget exactly how it worked but there was this, there was this the way that the sales and marketing teams were set up, they were fundamentally at odds. Like if, if a deal closes via marketing sales is pissed because like hey, you just took commission out of my, my pocket which is like well, how are you ever going to win in that world? Right? And if sales closes a deal, marketing is. Is pissed because, like, now their metrics look off. And so, so we had to fix that. Right. And, and those things all seem simple and obvious, but when you add in people and goals and incentives and competing plans, like, this stuff gets very complicated very quickly. And so unless the CEO is very clear on like a simple, clear plan that everyone agrees to, and then everyone has to go build out a strategy that. A plan that maps back to that strategy, that's the only way it's going to work is when your individual team goals are based off of the company goals. And so that means we're talking mostly as sales and marketing people here today. Right. That means that you have to. When you're thinking about your revenue goals for the company, it needs to be sales plus marketing equals X in. In some way. You have to go into this as a unified group if it's, if it's sales verse marketing, in that the comp plan for the VP of Sales is, is different than the VP of Marketing whose comp plan is all about MQLs and whatever. Like, that's going to be. You're going to be wrong from the start.

Yeah. And so the fix there, just to make sure I'm hearing it right, was moving to one revenue goal that sales and marketing jointly owned.

Yeah, the fix, the fix is like, let's back all the way out of this thing and say, like, what are we trying to. What are we trying to do? Book new revenue or whatever the goal is. Okay. And how are we going to get there? Great. And this is where. This is why, like, ABM is such a good idea. It's such a good idea for many companies is because in an ABM motion, nobody's arguing over about who, over who gets credit. Because the perception of marketing in that company is not like, it's like, more of like, marketing is supposed to assist us in closing deals versus in the other way. It's like marketing is supposed to close 200 customers on their own this month. Like, why haven't you done that marketing? And like, I asked Hillary Carpio, who runs ABM at Snowflake, about this on our podcast. She says there's no misalignment because, like, fundamentally, sales and marketing are measured together as, as, you know, team 1A and 1B as part of the revenue strategy. And so I think it falls apart at a lot of companies now because, I mean, how many companies do you guys see that they have Two different, they have a freemium funnel and an enterprise funnel. And then you have a marketing team that's supporting both. And then you have sales. You know, you know, Mary supports the freemium business, but James supports the enterprise business. And like, they need different things. Just with, right there with two sales reps, it's already complicated and just you create a ton of mess from that. And those are things that I, I, I still don't know how to fully deal with, which is like, probably why I'm working for myself. But you, you need to be able to think about that from a rep, from a company standpoint first before you go and layer on the sales and marketing tactics. You got to have people who know how to integrate sales and marketing.

And now we're seeing, you know, usage based pricing and deals become more common too. So people are trying to like, experiment with that in its own little world. See, it's, it's getting, oh yeah.

And then you got, and then you got expansion because everybody wants more expansion and, but where does expansion magically come from? Like, nobody owns that number, but it's in the plan. We're going to, we're going to generate $10 million in expansion revenue. And like we have two sales reps and then, you know, James from the content team is going to write some blog posts for them. That's not how this is going to work. Right.

It's maybe an expansion ebook. Not. No. Yes.

Yeah, we're going to, we're going to, James going to help them, help the SDR team pull a list and they're going to just email people and say, would you like to expand?

I love it. Okay, so I think that's great, great advice. You know, get that, get alignment. And you only get alignment through, you know, incentive structures being in lockstep. Going back to the first example when things were all good, you've got this conversational marketing messaging and you know, it's really landing. How did you keep the team engaged in that messaging? I'm sure it evolved over time, but would you have weekly all hands? Was your team remote? I feel like nailing a messaging is one thing, but then distributing it and getting people excited about it and getting them bought in and like the ongoing enablement is a whole other beast. So how did you manage that effective?

Well, the getting people excited about it part was not hard because the company was growing really fast and so there was a lot of stuff that was working without us having to do a lot of work on it. Right. And I don't mean that it was easy, but it was like, there was a lot of buzz. There was a lot of inbound. And so it was like, the customers that we were getting, the messages that we were getting, it was very easy to be like, huh? Like, even if you're like, man, I don't care. This is B2B software. Like, I'm just an engineer here. Like, we would even see those people be like, yeah, because it's just contagious. Like, there's something about being on a team, whether you're selling software or, you know, you. You have a community food drive or whatever, there's just something about that. And so I think that became, you know, winning was contagious. The company was doing really well. It was fun to smash the gong and have a new record and a new record. And that kind of just. That is infectious in a positive way inside of the company. And so a lot of it was that. A lot of it. And then the other part was like, I think there was a clear. There was a clear vision for conversational marketing today and, like, where the company is going in five years. And it was not a stretch in people's minds. And they saw clear roadmap to the future. And so I think people struggle when it's just very much like, this is who we are right now, today. Okay, cool. I can do that for, like, a quarter. But then all of a sudden, now it's like summer and half the year's over, and I'm like, hey, we said we're gonna do that thing. And so I think the product team was amazing, and they shipped really fast, and the founders had vision, and they ship really fast and delivered on that vision. And we told the story to the market, and the market continued to receive it. So you got to have all of the. All of the teams inside of the company, like, rallying around this vision and working to produce it. You know, it's like, it's not just marketing that's. That's doing this. It's like the. The product team is making better widgets, and, you know, the, you know, we're selling the widgets and the feedback is getting better. And so all of those pieces matter. I would also give us a lot of credit on the internal marketing. We. We spent a lot of time on internal marketing, and, you know, I spent a lot of time one on one with David, the CEO on internal presentations. Like, hey, like, we. We would spend oftentimes, like, more time because it's easier to do later. We got to make a big internal in two Weeks we need to unveil this like, new strategy to the company. And like that's what David and I would spend literally two weeks on inside of the company. And so people would be like, I, I, I don't know what he's doing. It's like, well, I'm in meeting where in, you know, I got to cancel all my meetings for the day and catch up on. David and I are writing some new vision and it would literally be him standing up in a conference room, you know, pacing at a whiteboard and I got my laptop and I'm like, you know, making slides and taking notes on the spot. We had such an amazing relationship from a creative standpoint. So we would spend a lot of time there on the story. It was never like we hired some outside agency to build us this narrative. It was very much like we were constantly messaging and texting and talking about the narrative and, and spending time on it and almost always used internally as a way to like pressure test something and do a lot of the work on the messaging. And then, you know, when you roll it out, like we would have this company ritual called show and tell on Fridays where at 3 o' clock the whole company would shut down and every company would kind of ship, would do like a five minute presentation on what they did that week or something. And I love doing that as part of marketing. And so basically every Friday at show and Tell marketing, we didn't just present the marketing metrics. We used it as an opportunity to talk about like the mission of building the leading conversational marketing platform, how that's going, where we sit in the market, feedback from people. And it was like it would, it would create buzz internally and get people fired up. And so it was a big, a big part of it was also the internal marketing.

Yeah, I think that's a great tactic that people can, can easily implement. This idea of a weekly show and tell, so much accountability comes from that. You can use it as, you know, not only an update, but also, you know, showcase interesting things that you want to infect the company with. And I feel like a lot of teams miss the internal marketing piece and miss that opportunity, you know, not only just to pressure test the ideas, but, you know, you're in a thousand person SaaS company that's a lot of different distribution channels you have through each employee and if you're infecting them with the right ideas, messaging and where you're going, you know, that's ultimately going to get you there much faster. I thought that was great. Okay, I Want to switch gears a little bit because we do have a part in this where we allow founders listeners to give us questions and this one is just stupidly relevant to you and a lot of the things you've done. And, and I think I'm going to take some liberties and actually expand the question. But the original question is, I'm a new founder. Should I start a podcast for my business? I'm going to expand that as should I spend time building out a founder brand. And as someone who has written the book on this, I would love your. Your take both the pros and the cons.

Yeah, I mean, well, I actually don't necessarily agree with you that I wouldn't, I wouldn't conflate starting a podcast with, with building a founder brand, right? Because we could say that starting, you could start a narrative style podcast about your company and you do this profile series. It doesn't have to be like, I am Dave the founder. I'm going to start the Dave podcast and build, build the founder brand that way. So I think that's one strategy. But I think what you're getting in my answer is, I would just. Sure is my answer. Like, I think any, I think any. I think, should you start a podcast? Maybe. Should you start a YouTube channel? Maybe. Should you do webinars? Maybe. Should you do email? Maybe, Like, I think it's more about like, what are you, what are you trying to accomplish with a podcast? And so for me, this always starts with like, what is the hook going to be? Why are you, what, what are you doing a podcast for? Do you have a, do you have a new idea that like, nobody in your industry has done and you want to, you want to start this podcast because you think you can build an audience there, or do you want to do it because you have 50 awesome customers and you want to make them stars and interview them? So I would just ask yourself a couple more questions first and then, but to be, to actually give you specific advice here, I would. If you do that exercise and you say, yes, I would start the podcast. If you are someone who enjoys having conversations, right. Having. Com. Do you enjoy having conversations or are you going to write, script and make it narrative? I do. See, oftentimes a founder wants to start a podcast, but then they are miserable at talking into the microphone. They, they don't want to do it, they don't want to make the time for it, they don't get energy for it. Right. Versus if you, if you, if you find you have to like, think about what Your natural skills are. And so maybe you are more of a writer. Maybe spend, maybe spend that time instead. It's going to take a couple hours a week, you know, writing a newsletter or just starting to contribute thought leadership content to LinkedIn, for example. And so I think a lot of it comes back to your. Your personal strengths. But a lot of founders are giving lots of talks and conversations all the time and they often have lots of connections inside of an industry and it's a very natural extension to then go start a podcast. So. So depends is my answer. Sorry, depends?

Depends is always like the only real.

It kind of always without a shitload of. Yeah, like, I don't know, maybe, maybe like your company is in a really boring niche and you're not an interesting person and you have no customers and you have no internal experience to help start a podcast, then like, no, but what if you're like amazing and a dynamic speaker and you, you know, 20 of the most badass founders in your industry and you want to go start the podcast? Like, yes. So there's a lot of nuance in any mark in any market. Marketing answer?

Yeah, Yeah, I think it's the only honest answer. I'm going to hijack the question a little bit and just selfishly ask one that I'm interested in because seeking wisdom back in the day I thought was very cool in its ability to discuss things that were relevant to B2B SaaS, but also give thoughts and ideas to things that are outside of just our little tech bubble that we all think about, you know, in our day to day lives. And, you know, it's almost like even more so back then you'd put like your work hat on and then you'd go put, you know, David Holmes hat on. And I think it did a great job blurring those. Those lines maybe for the first one at least in like a B2B SaaS kind of podcast. How did you measure success for that podcast? Because it was a little bit different. Or did you?

It's my favorite question. We never thought about measuring the success because almost immediately, a couple episodes in, the response was unlike anything that either of us had experienced before. And so it was like David would send me a DM of someone who said, like, who took a picture of them, like working out, listening to the podcast, and we're like, who the hell is this? And, you know, then someone else would leave a review and like call out something very specific. Or someone would send a book recommendation and mail a person a handwritten note to David in the Office. It was like, very quick responses on Twitter and email and in person. At the time, we were working in Boston in the Copley Mall, which is like a big mall downtown where there's a lot of shopping and offices. And David and I would often walk around the mall and go get coffee or something. And we were going down the escalator one day and. And a group of people went seeking wisdom. And we were like. Like, this is the. This is. This is unbelievable. And so there was just lots of little examples like that. And they kept building. And then it would be like a sales rep, you know, was, hey, I. I did a demo today with Okta and the, like, head of marketing at Okta, like, love seeking wisdom. And we're like, whoa. And so I think that was also the reason why it worked, right? It was like, not. It was a podcast with two people who worked at a B2B SaaS company who sold marketing software and would occasionally talk about the business. But people would hear about what Drift was doing. Not because we were, like, promoting products, but we were like, so in the past year, we've grown from 20 to 100 people. Like, like, let's talk about what that's been like, David. Like, you know, and blah, blah, blah, blah, blah. And then there we'd also. Then we'd also like, talk about music or talk about a book that we read or some other lesson. And so it was like reality TV marketing, I guess, in. In some way.

Awesome. Awesome. So I'll. I'll start kind of wrapping it up with two final questions, and I'll leave these intentionally vague. They are vague for a reason, so you can take it anyway that you want to go highlight something we already talked about or something that you feel strongly about. First question is, what is one tactic or strategy that founders or revenue leaders believe to be true that you think is BS or no longer relevant?

I think that some people obsess with measuring every. Measuring everything in marketing. And I think it's great that we've gotten so data driven, but I do think a lot of it is. There is a big science part of it, but I think there's a lot of art to it also. And I think it's very easy, especially now with budget cuts and people playing more defense. It's very easy to kind of shrink into this, like, defensive mode and just do. Just do paid and just do SEO and just do, you know, X thing. That's very easily measured where, like, coming up, especially through Drift, like, I was pushed by David and. And Elias and David, specifically on the marketing stuff to, like, not do things like everybody else, think outside the box. Not that that's a cliche thing. And so I think, and, and I credit so much of what we did to, like, there wasn't this pressure of, like, well, to what we just talked about with seeking wisdom. Like, we need seeking wisdom to generate six new sales meetings a month for us to keep it going. So, and so I think you got to be able to. To do things that don't have that direct, direct response measurement.

It, I, I like it. It. It doesn't allow much room for experiments or creativity if you're just following the numbers. Numbers don't. Don't get too creative.

But it's hard. It's also, I also understand that it's like, there's two sides of the coin, which is like, if you're never hitting your numbers and you're always behind and things aren't going well, it's tougher to then go and, like, get the freedom to go and do some, like, crazy, you know, unmeasurable campaign. And so, like, I've been lucky to be at companies where, like, things were going pretty well. And so it was like, sure, we want to go take a swing at this. Like, you, you can. So I do have empathy for marketers who are like, things are not going well. Yeah, it's not going to be the best time to go try some crazy strategy, you know.

All right, final question, brother. It's that one kind of flipped on its head. What is one tactic or strategy that has been working for you, has been working for people in the community that you think founders can implement, you know, tomorrow, and it will start, you know, moving the needle in the right direction.

I think a very under. It's not so much of a tactic, but I'm just constantly reminded of the power of a narrative and your positioning and your story. And so I think it's very easy to get lost and try to do 15 different things from a content standpoint. But I think the closer you can narrow down, like, what. How specific can you be to a specific group of customers? Not to double up on specific there, but, like, the more you can niche down and say, like, we. We are focused on this industry and these types of customers, and here's what we're going to do to go after them is. Is very, very underrated. And any mistake that I've made at a company is when we've tried to get too broad. And so, like, when I think of, like, in my company right now, in Growing Exit five. It was very, it would have been very easy for me to try to build like the biggest and be the marketing community and be B2C and oh, there's cool stuff happening in B2C. But so much of our growth has been because we made the conscious decision to basically specifically focus on B2B SaaS marketers and that has helped attract the right audience. It dictates what type of content we, we should create. I think you got to get back to basics and really figure out like that that you know who you're serving and why you can help them specifically is so underrated and it makes the rest of the tactics stuff easier. If I can give just like another half answer on this is from a tactic standpoint, stop trying to do 15 different things in marketing. It's going to be one or two very specific channels that make the biggest impact at your company. And I love to use the example from like Gong. I had Devin Reid on my podcast recently. But like the reason their content works so well is because they didn't try to do YouTube and tick tock and Instagram and a podcast and a newsletter. They were like, we're just gonna focus entirely on LinkedIn and we're going to develop content specifically for that platform and then we're going to drive people back to our site and get their email addresses and that was the recipe. And they focus on creating two long form, good research, original data type stuff a month. That works really well. I'm not saying that's the only way to be successful, but I would much rather see you have a very like opinionated and specific approach to marketing like that then trying to do, which is a mistake I've made a bunch of times is like we're going to do 15 things and we're going to be everywhere.

Yeah. And I think those two kind of go hand in hand. It's like niche down on a specific narrative, positioning, story Persona and then marry that with a simplified strategy, one to two channels. Again, simplify, simplify. I think that's, that's fantastic advice, particularly at the early stage. And we get a lot of early stage founders. Like if you spread yourself too thin, you know, that's the, that's the kiss of death. Beautiful. Well, dg, I appreciate you spending the time with the GTM community. Love what you're doing at exit 5. Appreciate you as a friend and a human. And if folks you know, want to follow along, pretty simple LinkedIn, Twitter, join Exit 5. Anything else you got?

Yeah, join Exit 5. That's it. Exit 5. Exit. Exit5.com.

Beautiful. Beautiful. All right. And to all those listeners that joined us, you know, I always say, listening's one thing, executing's a whole other beast. So apply some of these tips, strategies, lessons to your company, and we'll see you next week.