E47: Kyle Norton's Bets for GTM Domination (While Building a Generational Tech Company) - CRO @ Owner.com

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com. And every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

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Hey everyone, this podcast, as you know, is all about the cutting edge of go-to-market, and usually I bring that to you by interviewing CROs and other revenue leaders, and we go deep on frameworks and tactics that are driving success for them. But today the tables were turned. I was recently on the GTM Now podcast with Sophie Buonassisi, and we talked about our path to a billion-dollar valuation, to $50 million-plus ARR, a bunch of other fun milestones. And we covered a lot of ground and a good few topics that I haven't spoken a lot about on podcasts. So there's some new areas to explore. And I thought that might be valuable for this audience. One of the things I get feedback on is folks want to hear a little bit more from me. And so this is a way to bring that into our feed here and also to promote my good friends at GTM Fund. Sophie and the team do an awesome job on the content front. I love their podcast. I'm an LP. I'm wearing the sweater as we speak, actually. and so I thought you might find this interesting. So now for your enjoyment, my interview with GTM Now.

Owner is one of the fastest scaling SMB SaaS companies right now, going from $2 million to over $50 million in annual recurring revenue, over 10,000 customers, restaurants specifically, and now over a billion dollar valuation. Congratulations.

Thank you.

But that wasn't always the case. Like when you joined, churn was rampant. Sales wasn't really moving the way it should, the engine wasn't spinning. So what we're going to do right now is really break down the systems, the frameworks, some of the mindsets that you use to really take a company from $2 million to a unicorn status. Kyle, welcome to the podcast.

Thanks for having me.

Absolutely. Thanks for being here. Great to get together and chat in person. I always find episodes are extremely special when you're talking to somebody that also hosts a podcast.

Yeah.

Very different perspective.

Yeah, it's fun. I've loved doing mine, so it's always fun to be on the other side of it.

Yeah, definitely, definitely. I want to start at a very interesting decision that you made. 45 days into the role, you let go of half of the sales team. Pretty bold decision, and it essentially dictated the rest of the outcome for Owner, which is clearly a very, very positive growth trajectory. Why did you make that bold decision?

Any time you're trying to build a company that you want to take somewhere big, you have to make difficult decisions up front and lay the right foundations. And the first 10 people in your sales team, that becomes a lot of the fingerprint of what you build on in terms of their— their dedication, their drive, their intensity, the craft, the acumen. If your first 10 sales hires aren't at that, like, upper tier and bringing a level of intensity and drive, then it's really hard to build an organization that has that into the future. And so it was pretty apparent that there was some good sales talent on the team. 3, the manager and the 2 reps that remained after that are still in the business today and thriving and doing awesome. But, you know, we needed to raise the talent bar, and I got to work on bringing in folks who I thought were the right foundation to build something special. It was always my intention, I would've never left Shop if I, had I not believed this, but it was always my intention to try to build a generational company, to build something huge. That's what I saw in Adam and Dean at the time. GTM Fund invested, which is how I got introduced. And so from the very beginning, whether it was investing in systems, building out leadership teams maybe earlier than you otherwise would have, or making calls like that, it's always been about playing for a really big outcome and trying to make early decisions that gave us the best chance to do it. And that was one of them that certainly played an impactful role.

Definitely. And what were the other core decisions that you felt like were those pivotal ones?

Yeah, so having a really high talent bar, everybody that we hired in those first few quarters, and this is still the case today, but much more difficult back then, they were all President's Club performers, the number 1 or number 2 rep in the company that they came from. They were all 1 degree of separation away from me. They were people that I could, like, very easily backchannel and personally validate. And we didn't accept anything but the best. And so we've had an extremely high hit rate with sales hiring, especially on the account executive side. Very, very few people have not worked out, like less than 10% in the sort of 3-year history of hiring account executives. Our hit rate's been really good. So, high bar for talent and bringing in people that I could really easily validate. So, like, our first BDR was the cousin of a BDR that worked for me, like, 3 companies before that. And then there was, like, multiple people that came from the same company because they were all referred in, and I obviously had a, a strong back channel, or it was leaders that worked for CRO friends of mine in the past. So talent density, really high bar, and people that were— that I could really go validate were excellent and lived our values was number one. An early investment in systems and infrastructure. We spent a lot of money on tech and infrastructure much earlier than you would at like a $5 million ARR stage or a $10 million ARR stage. Again, because we were playing for this really big outcome, and I was trying to avoid the situation that many companies get themselves into where it's like, man, our Salesforce is a mess and we want to do this, but we have to completely change how we use the tooling or reimplement Salesforce. You see people go through. So we invested in tech very early, and I invested in people that were non-quota-carrying individuals to support quota-carrying individuals also very early. So I brought in my former rev ops leader on a contract basis in my, like, 4th month or something. We were like $3 or $4 million in ARR at the time. And I was like, hey, can you start doing some consulting for us? We want to build the right things. And I hired Steve full-time, I don't know, maybe I was like 6 months into the company, and he's like a senior, like, world-class RevOps practitioner. And that would have been way earlier than you would otherwise think prudent. You're like, oh, that's expensive, and that's a really senior person. Same thing with enablement, same thing with building the enablement team and the RevOps team. The data team was another big area of investment. In most companies, you'd look at that and go, like, there's so much CAC going into non-quota-carrying people. But that's what gave us the ability to scale at the pace that we scaled at, and it's why— a big reason why we're so efficient as a go-to-market org. So I'd say those are the three things.

One of the big lessons that we hear consistently, I wish I had done this earlier, is RevOps and investing in RevOps earlier and earlier. We're starting to see startups do that earlier and earlier, which is great.

It's advice I give to CROs and founders all the time. If you have legit product market traction, product market fit and traction, and you think that you have sort of figured out GTM, bring in RevOps. The way the world is going and the power of the tooling out there today, it makes so much sense to bring those hires in early. But people are really, I don't know, gun-shy about doing it. Big cost. We had like 6 reps and like a VP-caliber rev ops leader. In many traditional views, that is way too early. But man, it's paid off crazy dividends for us. But you have to be confident, and you have to be pretty honest with yourself that it's like, OK, our PMF is really good. We're really figuring out GTM. I think there's a path to a lot of repeatability, and I can scale. If you're growing 60% year over year and you've got like 4 or 5 reps, it's not the same decision-making, but if you think you've got the opportunity to go for it, then bring those people in earlier because we are all playing the power law game. Like, as venture investors, as founders or early executives of these companies, we're all playing this power law game where like a modest PE outcome doesn't do anything for me as a CRO, really, because you're going to get squashed under a pref stack, and the liquidity is going to go to everybody but the employees. That's just the nature of the game. And so you should be trying to go for the big win.

What's so interesting about what you just said, too, is the mindset you always had about trying to build a multigenerational company. Because essentially every startup wants to build an enduring company.

Yeah.

So every startup should really implement the principles that you just shared to build an enduring company and approach it with that lens.

Yeah.

Which is really, really interesting.

Not every company has the market size or the traction or the team to try to play for that type of outcome. And they really shouldn't be venture-backed. I think there's a lot of— a lot of the market's starting to— come to terms with that. You're seeing now people go this like seed scaling or seed strapping route where they raise a seed round and then don't raise again. And you keep a bunch of liquidity, you keep a lot of optionality as, as founders. But yeah, like venture capital is investing for those types of outcomes. And so if you have it and you have the seeds there of being able to do it, then you have to place really aggressively in my mind. The downside is if you spend aggressively and you didn't have the PMF, you don't have the market size, then you sort of spend yourself into the wall and you end up laying a whole bunch of people off. And it is really painful. So you have to be honest with yourself and know what game you're playing and decide what game you're playing and have a congruent strategy from your fundraising strategy to your product strategy to your go-to-market strategy. I think, like, CROs oftentimes don't understand those dynamics well enough, and they're not conversant enough in understanding the pressures of venture capital and how it works. And so you see early-stage revenue leaders complaining on LinkedIn. They're like, oh, the complaints like, oh, I was forced to do this thing, and it wasn't the right approach, and the founders are dumb, and the VCs are meanies.

Yeah, the fingers pointing.

It's like, that's the game we're playing. If you don't want to play that game, go do something else. Venture capital is investing in these businesses so that a very small percentage of them become extraordinarily valuable. And you need to understand that that's what you're signing up for, or just like go do something else, like work for a bootstrap founder or play a different game. But I think like strategic congruence is something that is sometimes missing.

Super, super interesting. And so You talked about sales and the reps you hired and how you hired them based on proximity. Churn was another area that you tackled early. How did that play out in terms of your go-to-market strategy?

So Adam and I started spending a bunch of time together after GTM Fund invested. Owner is Shopify for restaurants, basically. I was at Shopify. I had some early-stage experience. And so as part of being an LP, I was going to spend time with Adam to help figure things out. And very quickly, he understood it, I understood the challenge is that a bunch of inefficiency in go-to-market was because they were closing questionably fit customers and the handoff wasn't good. So the early churn was much higher than the company wanted. And it didn't make sense to pour a bunch of money into GTM into a bit of a leaky bucket. And so one of the first things that I tried to tackle was getting early churn into a better spot. And that meant narrowing the aperture of the customers that we chose to work with, and which actually meant month over month we sold fewer deals in my first month, fewer deals in my second month than my first month. But the metrics would show you that the quality was much higher. If you looked at high-quality revenue that we were closing, was actually growing month over month, but we were getting rid of a bunch of fluff. And luckily I had Adam's support. I have the sort of background and stature to do that and maintain confidence because that would probably be harder if you were a first-time VP of sales that doesn't have the background. But those were the right steps to take. And we got way more clear about expectation setting, which means some deals chose not to work with us. And we said no to a lot of customers. Like 30% of the customers that we could have closed previously, we were saying no to now. And it just cleaned everything up. And now we could go out and add marketing dollars and add sales headcount and add onboarding capacity into a system that had a lot less sand in the gears. Because many sales leaders don't like to admit it, but a lot of churn's our fault. At Shopify, I owned onboarding and CS at the end of my time there. I picked up the onboarding function in my first year at Owner. And so I've had to manage that side of the business, which I think is a very productive thing for revenue leaders to do. It's a good empathy-building exercise, and I think it's good from a decision-making standpoint. And we were able to get to a place where the sales-driven churn dropped dramatically, and then we could go tackle everything else.

Incredible.

Incredible.

No, that makes sense. And I mean, that's fantastic that you and Adam had that alignment and that trust built up. You're actually a perfect example of one of the points that you made around it's the people. It really matters who you're hiring. You were using the context of sales rep, but it applies to everyone. It applies to you. It applies to all of your leadership hires. How do you think about hiring? Because I've heard you say that you don't really buy into the traditional method. And I saw you comment on the Shopify Chief Data Officer's post that you do a don't hire with us video and things like that. I'm curious about your methods of hiring because every startup is trying to hire the best talent and you were able to do that early before Owner obviously grew to be the company and brand it is now.

Yeah, brand matters a lot. Like if being able to hire the right people means that you need a really compelling story and I've had the advantage of building an audience on LinkedIn over a bunch of years, which certainly helps. And I had a track record. So I encourage people to do that and like really be sharp about the narrative they're telling and how to get people excited. But the thing I think that's a little bit less consensus in our approach is two major things. Like one, and this is a big credit to Farhan Tawar from Shopify. So he was the engineering leader that I worked with in the point of sale team, who's now the head of engineering at Shopify. And he shared a bunch of data and like really interesting insight about how little a hiring process actually allows you to predict in-role performance. Like behavioral interviews and case studies and all of this stuff, a little bit of it is like theater. It makes us feel a lot better about the hiring decisions we're making. But when you actually look at the data, it doesn't actually improve outcomes all that much. But you have to be really data-oriented with hiring, or else you never learn that lesson. One is appreciating, like, what does interviewing actually tell you and what doesn't it tell you? And the other big principle that I lean into a lot is hiring is about fit. There's no, like, best rep. There's no rep that will be successful in every single scenario. You need to find reps who want to work the way that you want to work and reps that want to do the type of work you do. We sell to restaurant owners. They're like gritty, blue-collar folks who want to shoot straight and can be like pretty gruff at times and won't just like hop onto a Google Meet. Like you have to call them and help them get onto it. And some people get really frustrated by that experience. They're like, why can't people just like show up for the Google Meet? If you've sold to white-collar your whole life, then that might just be like a frustration for you. But the reps who are successful and something that I really enjoy is like selling to salt of the earth people and just being able to shoot straight and not like dress up our language in a bunch of tech jargon. And so for us, it's about finding people who can fit that environment and fit my style of leadership because we are quite opinionated about how we want to go to market and the style of sales that we teach is very specific and And the style of organization we run is like not for everybody, but some people it's like the best thing that'll ever happen to them in their careers because they're going to learn awesome skills that they can be successful with later. But, but it is not for everybody. And so the video that you're referring to is something that I do for especially leadership hires. There's like an explainer video where I talk about the situation of the company and what the role is meant to do and the state of the team. And then there's like probably 5 minutes at the end of the video where I'm like, okay, and, you know, Oner is an exciting place. And on the outside, everybody, most people would be thrilled to work at a company that's winning in the market and has all these accolades. But I was like, but Oner's not for everybody, and here's why. And I explain it's really intense. We're performance-based. It's not a great work-life balance culture. Like, that's not what we're optimizing for. And I explain the reasons somebody might not be a good fit. And I do that before their first meeting with me because the video is helpful too, because now in an interview I don't have to waste a bunch of time like explaining the basics. They come in knowing that and they can just get into much more interesting questions. But in the video I explain why Onur is like not a fit for people, and I have folks drop out of the interview process semi-regular basis. And I've actually had examples of people responding to that, responding to the video saying, hey, like, I really appreciate that you were so honest and transparent. It doesn't feel like the environment that's right for me, but like it's It's great that we could just figure that out now and—

Saves everybody time.

Everybody time. It's a good candidate experience. And it is— what you don't want is to hire somebody who doesn't know any of the bad things, the trade-offs, because it's not necessarily bad, but somebody who comes in not understanding any of the trade-offs. And then they're at the company for 3 or 4 months. They're not working at their best because they're like, man, like everybody works here so late. And like, I don't know, I don't— that's not really what I want to do. And they're stressed because they feel like they have to answer Slack after 5 o'clock, which is like not their shtick. And then they end up resigning like 4 or 6 months in, and you just wasted a colossal amount of time and energy, and you haven't progressed, you know, those strategic priorities that person would have owned, and you're just back at square one hiring that role again. And it happens all the time. We try to do that at the very top of the funnel, and then also like If we hire somebody and we can tell that they're struggling or it's not a fit, we'll often have a conversation, like an open, transparent conversation with them pretty early on and be like, look, Sophie, if this— I get the sense that this is— you're not having a great time. And if that's the case, that's totally fine. And we should just be like, let's have an honest conversation and solve it or figure out if this is just not a right match. And so when we have lost sales reps, most of the time it's very early. It's at the— we had one that was like less than 30 days. Somebody had 75 days because they've just realized it's not what they want to do. And that's a way better scenario than it dragging on and on and on.

Definitely, definitely better to find out earlier.

Yeah. The other thing we can talk about is going back to the first point about interviews being a poor predictor is—

let's unpack it.

Yeah. The exercise we just ran where we did a big hiring retro This is another area that is oftentimes missed in hiring is we hire and we hire and we hire and we never go back to that hiring process and analyze whether or not it's good or bad and like what we could possibly do better. And in product management, you do retros. In sales, you do MBRs or QBRs. But the most important thing in your business is being great at hiring. And we never go back with a critical eye to like understand it. And so what we did a couple of months ago was go back to every single person we've hired in 2024 and 2025, and we pulled in all of their interview scores by the hiring manager. And so we looked at a few different and compared it to in-role performance. And so there's a few things that we learn. So we use a 1 to 4 scoring framework and there's 4 people that score that candidate across the interview process. So they get a score out of 16. And what we noticed is there was not a lot of correlation between in-role performance and whether or not they were a 13, 14, or 16. Not a lot of— there were a couple of 13s and So there wasn't a lot of correlation. We're like, okay, so like something— it means like we're not scoring very well. And then you could go manager by manager and unpack. It's like, well, I was a 4 and the director was a 4, but this person was a 2 and this person ended up being awesome. Like, what happened there? And so you have to go give feedback to that hiring manager because clearly they're seeing something different. And to coach them up. But the most interesting insight, going back to this like concept that hiring can be a little bit of like performative theater, is the case study scores had like no correlation, actually were inversely correlated with success in role.

Really?

So the people who crush their case studies didn't really do any better in the role versus the people who we hired that didn't do well in the case studies. And if you think about it, like if somebody did poorly in the case study, but we hired them anyways, there must have been a bunch of other stuff we really liked to get over it, which in our case was their like raw DNA. And we're looking for super competitive, driven people. You have to be really organized to do what we do because there's a lot of— you're managing a lot of deals. The velocity is very high. And so if you're disorganized, it's hard to be successful at Owner, which is like not a common thing to screen for in sales hiring. And so we started to tweak how we thought about the case study, and we've really now weighted DNA and mindset more highly, even in our SDR cohorts, especially in our SDR cohorts, because none of them are going to come in with that much skill or craft. It's really just all about DNA. So we haven't done it yet, We haven't been brave enough, but there's part of me that makes me want to like scrap the case study altogether because it's so unpredictable. But unless you're doing the work to analyze your results and to take a critical eye and do that retro, it's hard to calibrate on hiring.

I can imagine, especially at the velocity that you guys are hiring.

Yeah, yeah, yeah. It's helpful that we hire like we'll hire 100 people in go-to-market this year-ish. And so we have a cohort to analyze, but you could probably still do it with less.

Yeah, yeah, definitely. And what about leadership? Does it differ, or are you still thinking about it from a very DNA perspective?

Slightly different, but DNA still matters a lot. I think the biggest lesson that we've learned on the leadership hiring front is the importance of philosophical alignment and congruence. And so there are so many different ways to lead people. You know, like we have a very servant leadership-oriented approach. We are very systems engineering-centric. We're trying to build like high repeatability. And if somebody comes into the business that has like a slightly different perspective, on your core tenets, then it can be very, very difficult for the organization, especially if you're bringing in somebody senior. And so what we've seen with the most successful leadership hires is that they're people that have a very similar mentality and set of principles, and also people that are very adaptive. I think this is the other thing that I like underweighted historically in leadership hiring is, and this might be because like, again, I am very opinionated about many things go-to-market. And so, but which means I require people who want to learn my system. And so the leaders on my team are so productive because they use the same language, they refer to the same books, they talk with this common vernacular. So when I'm talking to the reps about something, in a recorded training or a town hall, it's the same language they're hearing from their director, from their frontline manager, from their peers. And it seems like semantic and a little bit silly, but just getting to common language is so critical. And so you need leaders that are willing to adapt and to operate within your system. I find maybe that's like a little unique to me because I'm so particular or so opinionated about it. But, but like, that's something I need to understand about myself and the system the organization we're building, and know I need to go higher for that.

Kind of makes me think organization, organism. You think about different blood types, like you're hiring all type A bloods.

Yeah.

Or type B plus or what have you, right? Somebody that's got that congruency baked in.

Yeah. And it's a careful balance because you don't want to just try to replicate yourself. You need some diversity of thought and background in You don't want too much of a monoculture. And we try to operate by the principle of opinionated but open. So I want people to be opinionated and think critically from first principles and not to just accept things because that's the way we've always done them. I want people to disagree with me, but I want people that are also open-minded. And I try to be open-minded about new ways of doing it. And so you have to find the balance here between that congruence. And a good example is, you know, with my VP of RevOps and I, like, he's the guy that will disagree with me the most directly and be the most brave about it. We've worked together for almost a decade now across 3 companies, and it works so well because we can just like have the argument. We can try to like look at the data together, disagree, and sometimes we like can't get to the same answer. Like we just have slightly different opinions. And ultimately I'll be like, you know what, This is your call. It's in your wheelhouse. I trust you. Like, let's go for it. Or he'll do the same with me. There's a lot of nuance there, and you have to find the balance between like avoiding, avoiding an echo chamber, but also having like having congruence on the really important things. Like servant leadership is a non— it's a non-negotiable. Like you have to operate with the mentality that you work for the people that work for you. The managers work for the reps. I work for the reps and I work for my leaders and the reps work for the customer. That's a non-negotiable for me. But there's other things we can be like more fungible about.

So you're hiring 100 go-to-market reps this year alone. So you're growing a ton. And you've been really successful with your AI transformation. Love to hear a little bit more about your playbook for implementing that transformation and what you're doing.

Yeah, and so we were really early to try to steer into this in a big way. So some of it was like just getting lucky and following our intuition because there wasn't a lot of places to go learn from. And luckily, like, I have this podcast, I talk a lot about GTM AI, and I get to talk to a bunch of smart people who are doing things. So having a network and using your network is definitely important. But we've like meandered our way into or intuited our way into a bunch of good decisions. And now that I've had some distance from it, I've started to like put some principles behind it that I think are fairly reasonable. But again, this is so new that like I reserve the right to change my opinion over time. But one of the things that I think the most important thing that we, that we did right and a principle that now I push people on is we spent most of our GTM AI energy on data. So the very first thing that we did, and this was led by our head of Biz Ops, he gets all the credit, was figure out prospect data. And so we used AI to scrape and crawl websites and pull information into Snowflake and transform it and score it and figure out who the very best people are that we should be approaching. So getting really great third-party data was step one. And so now when I give this advice to other founders and revenue leaders, I'm really pushing them before anything else, Get really great third-party data, and this could be like Clay plus a Claygency to help you like answer a bunch of these questions or an internal data science resource, but like some spend the money, get good data on the market, your accounts, people, and then enrich with like information that can help you with the right play for that, for that account or prospect. And so like now we use Datalane for a whole bunch of this stuff because it's restaurant specific and they've built better things that we built internally. But the big— the first investment we made here was getting good third-party data. And I— in that we were not— I didn't at the time go like, I want to be on this transformation journey with AI. But like, I think the third-party data is the first thing we sort of intuited our way there. But now I feel good about that as a principle. The other thing is great first-party data. And so this is where Momentum comes in. This was like our second really big AI application where, you know, there's all of this information in call transcripts and in emails and like all across the customer journey that, yeah, you can go access, you can pull open Gong and like read a transcript or search a transcript, but like it's not all that helpful programmatically. Unless that data is structured. And so for Momentum, it used to be on top of Gong, and then we replaced Gong, and now we use Momentum as the call recorder, which has been great. That will take all of this information and put it into a structured format so that we can actually now power a bunch of analysis off of it. So it can answer specific questions. Did the rep say this or that? Like yes or no box. Is the customer using this list of 10 competitors or something else? Or open text fields. What were the challenges that the customer is like most interested in solving, like ranked 1 to 3? So you start to bring structure to all this unstructured information. And now that I have good first-party and third-party data, I really have a very different understanding of the business. And you can make such— you can make much, much better decisions. And how we do it in SMB is a little bit different than how you might do it in in enterprise. Ours is like a data science-led motion because the TAM is massive and there's so many data inputs in an enterprise environment. I'm using AI more to deeply enrich accounts with specific information, but you're writing those prompts thoughtfully. And so I would say the biggest thing that we've done is start with the data foundations, And now when we layer on a use case, it's so much more effective because AI is just a pattern recognition machine. And but if you have good patterns for it to learn from, now we've got— we use OneMind as this AI SDR education avatar. So you can talk to an AI version of our founder about anything related to restaurant marketing, and it can explain what you should be doing better based on your specific website because we've got this AI website grader. But that all works because we've got this corpus of information to work from. So I would say that's probably the single most important thing that we've done. Start with the data foundations.

It kind of sounds like how you built the go-to-market engine. You started with rev ops, you started with the data foundation, and then you built on top of it too.

Yeah.

Same thing coming back to the data first.

Yeah. And even if you go one level of abstraction out, it's like we just start with the boring stuff. And I think the— That's one of the places that people go wrong with AI is like they want to chase the shiny things first. And this is a Jordan Crawford thing. He's like, people need to eat their damn vegetables. Like, you have to do the hard work on the data foundations. You do have to do the hard work to really thoughtfully decide who is your ICP? What are the key segments? What is the digital footprint of those specific high-fit segments? What is our positioning? What are the specific things we want to say so that you can feed that into these models so that when you are producing either cold outbound messaging, that it is sharp and on point and not like AI slop? Or when you see so many startups trying to do this, like, oh, we're like a sales copilot. We'll tell you what play you should run. We'll give you all this account information. But So many of these tools go wrong because it's just like generative layer over generative layer of probabilistic reasoning. And you've never inserted deterministic constraints onto this model. And so you're just stacking, like in AI it's called lossiness. So you're just stacking layer and layer of lossiness on top of each other. And so your tool is like, oh, enter in your company website URL or company URL and we'll give you sales messaging. You're like, wonder why the sales messaging sucks? Because the model had to view your website and take a guess at what your positioning is and take a guess at what your ICP is and then take a guess about the challenges and who you want to talk to and this and this and this. And every one of those guesses is probably going to be like pretty good. But if you stack on these 10 guesses, it's like broken telephone as a kid. You just end up with something that's like, like, It's, yeah, like it sort of is what we do, but like it's not good enough to send to a customer really. People still send it to customers, but that's one of the problems. It's like people aren't inserting enough constraints on, it's like, no, like I will tell you what our positioning is. I will tell you what the ICP is and the digital footprint of that ICP and then The AI can use all of the wonderful generative capabilities to go find all of the people and all of the evidence that supports the specific criteria of your ICP. Like filling in a smaller set of blanks, we found to be very, very helpful rather than just like letting AI answer every question and make every determination in a system.

It sounds like the lesson for founders and operators would be don't replace your, your actual foundational work around the company, your positioning, messaging with AI at all. Do the work and then use AI to scale.

Yeah. Or use AI to help you get to that answer. But there needs to be a deterministic layer because, you know, like even for me writing, like I use AI a lot as a writing copilot, but I'm I'm always editing and changing and tweaking, and I'm like, no, that's like obvious or silly. And so there's always a process of me being human in the loop and like making thoughtful decisions rather than like we really avoid AI making like many sets of decisions on top of each other. And this is a reason I like Momentum as well, because we can write the prompts that fill out the specific fields. And so we get the power of AI, but within this constraint. So it's like, tell me, like, tell me what the next step was that was discussed and then maybe suggest based on other interactions what next steps could be. But then a rep has to go in and like adjust that before it just goes off and starts executing workflows.

Got it. So it's not autonomous, essentially. It's doing the hard work and then prompting the rep to give it some instruction and then go off.

Yeah, that could, that could be the architecture. The important principle I think for people is, is being thoughtful about combining deterministic decision-making and workflows with the generative side of things. Like that's where we've seen the most success, even like our AI website grader. You know, we are thoughtful about the things that we're, we're telling the grader to go think about and analyze. It's not just like an AI free, freeform, like, tell me whatever you want about these websites and you make the decision about what drives good conversion rates versus bad. Like there is a lot of AI-driven decision-making in it, but, but there's also a constraint, which is where, which is where which is why that output is so powerful.

Mm-hmm.

I just see this pattern all the time. Like, you just need the deterministic constraint somewhere. It could be a human in the loop. It could be you, like, setting the rules within the agentic workflow. You just can't let AI layer 7 AI steps on top of itself, or else you start to meander and get to slop territory.

That's great advice because I think that's what a lot of people are trying to do is trying to automate as much as possible and create more of a waterfall effect from it. But it sounds like you're saying, you know, be really intentional with how you're actually putting the inputs in along the journey.

If it feels way too easy, it's probably— if it feels too good to be true, it probably is. Like even, you know, being really mindful about the prompt engineering and spending the time to build the evals and run, change the prompt and run the eval, run the eval, run the eval, like going and doing the work to really like test and iterate and tweak the context engineering that is involved in, in these workflows. Like you can't— the out of the magic box answers of like, oh, just enter in your website and we'll tell you everything. I have— I've yet to seen those tools work all that well. Versus something that, like, you know, why I chose Momentum over a bunch of the other tools is because I could go write the prompt and I could go set it up with that specific field and then we could run it. We would run it. I would look at the end of the day and look at the fields that it filled out. I'm like, okay, well, it's actually, it's like giving away too much. And it's like one of the things that I'm like, we use a call recording tool that's for interviews that I won't name because I'm about to trash them. But like, The transcript summary is like, "The interviewer asked the candidate about whatever. The candidate responded, yada, yada, yada." I'm like, "This is a completely unhelpful transcript 'cause it's so long and it tells me about stuff that is obvious." It's like, no, just give me the answers to their questions based on the lever, our ATS, the Lever feedback form. But because it's just, there's no constraints, we haven't like, we're not able to do the prompt engineering in that tool versus like we can do the prompt engineering in Momentum. So the results are way better. And so it's funny to see these two things side by side. One that my RevOps team spends a bunch of time tweaking and testing, one which is just like hiring AI black box that gives me like unusable junk, basically. Mm-hmm.

Mm-hmm. Super interesting. And I mean, we're seeing a lot more founders, leaders use AI to write content and publish it online. And I've heard you say how monumental or impactful it was to actually build a brand for your recruiting early. You talked about that. What are your thoughts on actual content creation for founders and early-stage operators? Should everyone be building their own personal brand?

Not everyone, because not everybody has like a ton to say that's all that interesting. And it probably won't— you'll put a bunch of effort into it and you won't get the result you necessarily want. Like, I think people who are successful creating content have something unique to say and they're able to bring new ideas to the table. And you have to like it, like you have to enjoy writing and enjoy putting your ideas together and spending time looking at a page and being like, oh, the taxonomy of how these things fit together, it's not right. I want to do this. I want to do that. And so, because it's a huge commitment. I generally like writing and I write, I wrote a lot internally. And so, I just started open sourcing stuff that I was writing for my teams or training docs in little bite-sized components, and so it was enjoyable for me, and so it wasn't like a taxing job. Some people don't want to do it, and it's going to be a chore, and you'll never be that successful at it, I don't think, if it is a chore. But I think today, like, you know, it is— the market's very competitive, especially competing for the top talent is very, very difficult, and having a brand is meaningful there's other ways to solve that problem on talent attraction. You could just be like a hardcore outbound sourcer. So earlier in my career, that's the game I had to play. And I sharpened my messaging, and I did a bunch of outreach. And so I think for the right person, it makes a ton of sense. And it was because of Naval and Seth Godin that I really started to be like, I got to build an audience. I have to build a brand because it's a compounding asset. It's something that I'll take with me for the rest of my life. And I'm like, so bad at monetizing it. Like, I basically don't bother. It's really just about hiring. And I have friends who, like, make a bunch of money doing content stuff and influencer stuff. And I'm like, it's just not— it's like, yeah, I should. But at some point I will be able to.

Right. You're busy. You're busy hiring people.

Owner's the only thing that matters. And all the other stuff, like podcasts and content and speaking stuff, like that's all to build my brand as a hiring leader and Owner's brand as a destination. Like the number of eyeballs that Owner gets just because I'm out there doing a bunch of stuff is awesome. And it's gonna help us in a bunch of different ways. But you can build this compounding asset that you can monetize in a whole bunch of different ways. So if you like it and you want to spend the time, I think it's worth it. But just know, like, you're signing up for, like, years of nothing, basically.

Right.

And maybe I could have been more thoughtful about it earlier and grown faster, but, like, there's just a cold start problem where it takes a while to get it going and you have to be so consistent because if you miss a week, then LinkedIn crushes you for it. And so you're signing up for like a long haul thing, but it is a compounding asset. So over time, like now I just gain followers like by doing nothing and it's— and it grows very quickly. But, you know, I've been at it for like 6 or whatever, 6 or 7 years.

I don't know. Yeah. Yeah. Yeah. Now you're on the hockey stick momentum and trajectory. Okay. So you said you bring that with you everywhere. So, so do connections, connectivity between people. You bring a lot of your relationships with you over time. And I know you implemented BDRs being in office 5 days a week, which is a common point of contention. And I have a lot of opinions too, because we're actually in the office 5 days a week.

Yeah.

But you've had a lot of growth and success on the revenue side. So does that settle the debate on in-office versus remote?

No, the debate will never be settled and it's very nuanced. And I had the CRO of Oyster on the podcast, Geraldine, and they're obviously— they're, they're like an EOR company. They're very pro-remote. A bunch of the content their founder puts out is like super remote's the only thing and it's— it lacks nuance. But the conversation we had was, was like very nuanced and productive because remote makes sense for some companies. In-person makes sense for some companies in some roles. But again, going back to this theme of like congruence, like what is the thing that you're building and what serves you best in terms of a strategy? Because if you are remote, but you're like not great at documentation and you are like not taking advantage of hiring internationally, then you're sort of just sacrificing the connection, the speed, the engagement that by not having people in person without getting all of the outcomes. And so, for example, most of our sales team is still remote. Our outbound sales, our AE team is almost entirely remote other than the brand new AEs we've hired very recently. But the SDR team is 5 days a week in office. That's the requirement. And yeah, absolutely. The performance between remote hired SDRs and BDRs versus in-person has been drastic. Like we pulled the numbers and it was like grain of salt because it was a small sample size, but it was like the ramping performance. So in that first 90-day window was like 3x for in-person than it was for remote. And, you know, the system's more mature now. We, we've revamped onboarding, so you can't chalk it all up to onboarding, but those roles do benefit so much from being around their peers and being around their manager. Like when I'm in the office, the managers are always sitting like hip to hip with one rep going through workflows, really inspecting things. You know, my VP of RevOps was in the office 2 or 4 weeks ago sitting there beside the SDRs watching them dial. And we realized a bunch of stuff. We're like, oh my God, we thought they were doing this and like The system is designed this, but we didn't enable them properly. And so there's like this big hole that we found. And you can, you just like, there's some big advantages, but the strategy moving forward, and we haven't nailed all the pieces, but generally we're going to have like BDRs and SDRs in the office 5 days a week. There's, because you just, it's so input-driven and it's so hard to do that job if you're sitting at home in your tiny little apartment with with all those distractions. So they'll be 5 days a week. We'll graduate people into associate account executive. Their first, you know, 3 to 6 months is probably also 5 days a week in person. Once they start hitting quota, then we'll graduate people to 4 days. And then once they move to an outbound AE, now they've been an AE with us for 18 months, maybe 24, we'll make it 3 days a week. And then once people move to our highest segments, we'll say like, look, Come in as much as you want. We would love to have you. More is better, because then other people get to learn from them. But we'll basically tell them that they can be fully flexed, come in when they want, don't come in when they want. Because I don't— I'm not worried about them anymore. I'm not worried about a multi-lok— or in our highest segment, but our top segment reps lacking motivation, or not understanding the process, or needing the deep coaching that an earlier stage rep rep would, and they can operate great fully remote, and it's easier to— it is still way easier to hire people remote. Like, reps want remote. Like, there's no doubt. Sometimes they want it, and it's actually not the right thing for them, but it is an expectation in the market. And so we're trying to find the middle ground. But like, engineering's still all fully remote. I'm in person with the whole exec team here in San Francisco now. Same with like a bunch of product leadership. So that makes a lot of sense. But, you know, there's still tons of people that are remote at the company. So we're not hybrid. Like, I don't know what you would call Owner Now. Hybrid implies to me that like everybody is in the office sometimes. We have a bunch of people that are never in the office really, other than for offsites. We have some people that are fully 5 days a week in person. And so Some roles yes, some roles no. It matters by like the role type, the seniority, and just trying to find the right balance there. Even just as you get older, you have so many more life demands.

Yeah.

Like I got two young kids. Like I go in the office a lot because it's like productive and I like it. But yeah, some days I just, I have to be home because something is going to go on. And so try telling like a 35-year-old enterprise rep, then it's 5 days a week. You're not going to hire anybody good. So you just have to meet the market where it is and try to find the right things. But you have to really think critically and think from first principles about the decisions by role and not just be like, remote is— or like, in-person is bad. It's like, people make it this silly moralistic decision. And there's a bunch of people on LinkedIn that are like, oh, it's like— It's unkind or it's unconscionable to force somebody to go in, and you're like, grow up, man. And you just, like, if you believe that, then build a remote company. But like, that company—

Like what you said about venture, like, there's other places. Find those places that you agree with and that resonates with you.

Find the place and be honest with people about it, and it's all good. It doesn't need to be this, like, in-group versus out-group argument. And it might evolve. Like, you might be in-person as a startup when you need all 5 people shoulder to shoulder. And then when you need to hire 50 engineers in a year, good luck doing that if you founded your company in Dallas. Like, no, no, no, you're remote now.

Yeah, yeah, exactly. So, so much context.

Okay.

And you've got, I mean, a ton of leadership principles through —this even remote structure, but all the things that you've shared around the good market strategy, the hiring, what's a core leadership principle that you just take everywhere? So I have a bunch. Yeah, I'm sure.

Servant leadership is at the heart of it, which we've already talked about. This idea that it's all of our jobs to figure out how to enable the people doing the hard work, the people on the front lines with customers, to do their best. To do their best work so that they can be in service of the customer. Like, it's always about the customer. So servant leadership is number one. And I just actually recorded my podcast with my VP of RevOps because a bunch of people asked me to do it.

Oh, I can't wait to listen to that.

And one of the conversation, one of the design principles we talked about that's been so important for us is building RevOps infrastructure and business process in a way that helps do the right thing as the easy choice. And so like removing friction from the stuff we want them to do and just like being extremely rep-centric in how we make decisions and prioritize projects. And, you know, really he calls them quality of life improvements. We ship a lot of quality of life improvements for our IC team. So servant leadership is probably number one. The other one that's the most important for me is like growth is the thing that we should be optimizing for—personal growth, professional growth, company growth too. Because if you are growing as an individual, investing in yourself, trying to learn and get a little bit better every single day—this is Darren Hardy, Compound Effect—like, you can compound those little improvements over time to be exponential. And so the biggest investments we've made as leadership team, as an organization, as a GTM organization, is in our enablement function, onboarding and training and development. Our managers are psycho coaches. Like, I will— this is an open challenge for anybody listening to bring me a frontline management team that spends more time coaching than my team does. We are like so hardcore about it every single day, multiple hours a day. We do this thing called chop wood, carry water, which is like you're not allowed to have meetings in the first 3 hours of the day. The managers, all they're allowed to do is be hip to hip with their reps and be doing ride-alongs or practice or something to move, move the rep forward. The growth thing is the most important thing. It's what I'm really passionate about too. Like, you know, when I was growing up in high school, I taught preschool art and then I taught martial arts for years and years. And when I got into sales, like, I wanted to teach people right away and I became a manager very early and It's the thing that I get so much fulfillment out of. And so I think a lot about, and I study, and I read a lot about how to develop skill and train people. And, you know, I really want people to come out of their time with me feeling like they exploded in their career and they learned all of this stuff. And like the— The mantra that I have for myself is I want to give people the best years of their career. Like, that's the expectation that I set for myself and for my leaders, is that the 1, 2, 5, 10 years that any of these folks spend with us, those should be the best years of their career because they learned a lot, they felt like they made an impact on the world, they won, they felt supported, they could trust the organization. They made money, they got promoted. That's really what we're trying to do because I think if you can do that, and people really truly feel it and believe it, then you'll hold on to your top talent, you'll attract great people, you'll get the best out of them. And we want to help people find their internal drive and purpose and motivation as opposed to being this environment that's just shoving people forward, right? Because then they can take that, like, internal locus of control, that intrinsic motivation and drive to whatever they do next. That, that's like one of the most important things we try to kindle.

That is beautiful. And what about books? Any favorite books that have been really impactful for you in your career?

A ton. Yeah. So the book that I think everybody should read is Thinking Fast and Slow by Daniel Kahneman. It's— he's the him and Amos Tversky are the creators of the field of behavioral economics. It's like much more in our zeitgeist today than it was when I read it when it came out over a decade ago. But it's like how humans operate and why do we, how do we act, why do we act in these like very irrational ways sometimes. Predictably Irrational is another great book in that category. Nudge by Daniel Kahneman. Richard Thaler. I think there's a bunch of interesting things in the behavioral economics world that once you start to understand, you're like, oh yeah, that's why my reps do this. That's why these people operate this way. So those are all great books. The book Servant Leadership is a really good one. Messaging, I love Made to Stick. That's one that I recommend a lot. And then Atomic Habits is another one that I recommend to every rep that works with us, every one of my leaders. It's like something we steer into. The other one that's on my, like, leadership, like, mandatory list is The Obstacle Is the Way by Ryan Holiday. So those are some of the, like, starter— that's like the starter— starter pack. Kyle Norton leadership starter pack. Yeah. To get people going. And I got to update my reading. I published my, like, longer reading list a bunch of years ago. I have to do a big update and put it on LinkedIn, but I'll make that commitment. I'll do that in the next couple of weeks when this comes out.

There we go. There we go. We've got a commitment out of it. Yeah. And Adam co-founded and is the CEO. Yeah. Of Owner. He's a Thiel Fellow. I'm curious, what is it like to work for someone that is a Thiel Fellow?

So I don't know if it's because he's a Thiel Fellow per se, but Adam has really set the standard for like what I think the bar is to be a founder and build a generational company. I've worked— I've gotten the opportunity to work with really great founders. The founder at League was like a third-time founder, two super successful exits. Obviously Toby's like the GOAT. I have like, I still, any podcast he does, anything he writes, like I read and I have insane respect for him. But I never got to work with somebody in the early stages of their journey. Adam was like 23 when I started, when I started at Owner. And so I got to see like what the raw building blocks were of somebody that I think has the opportunity to build like a truly great company, which has been really informative And so, like, one, he was just a force of nature, like just this insane drive and presence and willpower and work ethic. Like, nobody— it's funny, like nobody had ever made me self-conscious about the amount I worked until Adam, 'cause I was always like the hardworking guy. I was always outworking everybody. And so it was like a weird— it was a weird thing to be like, whoa, like I'm not the hardworking guy anymore. This guy's sort of running circles around me because he's just like an absolute machine. And so, like, he's a force of nature and very charismatic. He's a great recruiter that I put into this. Since meeting Adam, this is like my new founder evaluation framework. Are they a force of nature? Are they a supercomputer? Do they just have like— not just are they really smart, but are they like freakishly smart? And do they learn at an obscene rate? And so the story I always tell about Adam is like I mentioned this book offhand, Made to Stick, that book about messaging. We were on a call and talking about messaging. I'm like, oh, there's a book Made to Stick that I really like. And then he texted me 18 hours later and was like, hey, I read that book and then had all of these questions. So it was impressive. He read a book in like literally less than a day. But then he was drilling me with these questions. I was like, man, these are questions that I should be getting from somebody who's like a deep product marketing expert who's got like years and years of building sales messaging. He had like really cut to the center of the first principles of that book and was asking me really hard questions that I'd never gotten about the book. And so that was like, okay, like supercomputer. Then founder-market fit was the other thing. Like, is there some reason this founder should win in this market? Yeah. Adam built Owner for his mom. Like, he's so deeply passionate about about helping small businesses, and he's still so close to the customer and has such a crazy customer intuition because he does care. And I think it's really hard to break through the $20, $30 million ARR mark unless you have that true founder market fit and that founder secret. And the last thing is, enough humility not to blow it all up, because I've seen a bunch of founders that have a lot of the other stuff in the Venn diagram of like force of nature, supercomputer, founder-market fit, and also humility like that. That sliver of the Venn diagram of humility overlapping is a very rare one. But they need to have enough intellectual curiosity and humility to when you hire senior leaders to actually give them the rope to go. The amount of CROs that I talk to that complain that their CEO is way deep in the weeds and making sort of weird decisions on stuff that they don't have a ton of context on is crazy because they don't trust and they don't have the humility to be like, OK, I wanted this person to make these decisions. And Adam has done— I'm very grateful for the rope he's given me to build this thing. And so you see it, the like, I don't know if it's an employee count number, it's like an ARR number, but like the $10 million ARR number, like 100 employees, whatever the number is, things just start to like fray and fall apart for those founders who can't touch anything every more, touch everything all the time now. And so like that humility piece I think is really important. And Adam's done an admirable job listening to feedback from the people in his network and being open-minded about the decisions we make internally. And he asks thoughtful questions and he will go founder mode on stuff he feels good about. And when he does the founder mode thing, I'm like, all right, like, because he doesn't do it all the time. And when he does it, he's like being right almost all the time. And so you just got to trust and be like, okay, he's got some insight, some intuition. I don't have the customer intuition of this specific thing like he does. That's why I chose to work for him. But there's enough of the humility there that it all works. And it's something around— I'm curious on people's opinion on this, so shoot me a note. But like, it's like 100 employees or something around there when you can't touch anything anymore, but the founder still is trying to hold on to everything, like with an iron fist, and it just all starts to fall apart. You can't keep great people, you can't attract good people. Now you're like being pulled in too many directions. But like, that's a pattern that I've only picked up on in the last like 3 to 5 years. But now I see it. All the time.

Interesting. Interesting. Yeah, that's incredible. And where can people find you if they want to follow along?

On LinkedIn is the best place. Or follow the podcast if you really want to go deep on revenue leadership stuff. It's me going usually super deep on one topic that, that, that person is an expert in. It's a lot of fun for me. I would probably do it if nobody listened to just 'cause I learn so much every week. And it's therevenueleadershippodcast.com. It's the newsletter, the podcasts are all there.

It'll be in the show notes for anyone who has not read or listened to it. Highly, highly recommend it. It is incredible.

Thank you very much. Appreciate that. And LinkedIn. And LinkedIn. And LinkedIn. Yeah. I have now moved to San Francisco and dealt with a whole bunch of stuff over the summer. So I will be back on the content. Generation Horse soon. It's funny, I have a widget on my phone, like a to-do list button, so I can jot down ideas as they come. So I was running today, and I was trail running, so I'm trying to scrape my phone out of my pocket to put this idea in. So I got a backlog of things that I want to talk about that I'll start to jot down. That's amazing.

We'll look out for them. We'll know. The purest kind of ideas have come from running.

If you can hear me panting through the newsletter, that was—

That was one of these.

Yeah, on a run or on a bike.

I love it. Well, thank you for joining us. This has been fantastic. It was a pleasure.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes and be sure to leave a 5-star review. Share it with your network. Work, and please join me next Wednesday for another great conversation.