For a while, I felt alone in our ecosystem. Most people I talked to were optimizing for an exit — an end to the journey. But, I wanted to do this forever. Was I naive?

Then I found The Founders Podcast. David Senra studies history's best entrepreneurs, and a few episodes in, something clicked. One founder was asked about his exit plan. His answer: death. I wasn’t alone!

Interestingly, David rarely dwells on strategic insights or tactical takeaways — those are too subjective to be broadly useful. Instead, he focuses on how these people thought and navigated pivotal moments. That's where the real learning lives.

So that's what I want to do with this Q&A series: sit down with the best  GTM leaders, dig into how they think, understand their mentality and share what surfaces.

First up: Kyle Norton, CRO of Owner.com. Kyle joined at $2.5M ARR; they're about to cross $100M now. That kind of scaling usually requires 2-4 people in his seat. When someone breaks a pattern, we should figure out why.

We barely talk about AI in this one — which is a feature, not a bug. Instead, you'll learn how his job has evolved, how he thinks about the bets that matter, and how he's equipped himself to scale. Enjoy!

Asad Zaman: When you joined Owner.com, they were around $2.5M in ARR, and next year you’ll be past $100M. How has your job changed from when you joined as SVP at $2.5M to being the CRO now heading past $100M? 

Kyle Norton: Yeah, it changes drastically and I think in the first two years it changes faster than in the following years. The team I inherited had four reps and a manager which I ended up converting to be an IC sales rep. He's still like one of my best reps. Essentially, I was a frontline manager when I started. I was back to coaching calls and writing scripts and managing a forecast and sort of like doing that job on my own. Then, eventually, I put in a first-line manager who could do more of that. Then I had multiple managers and so I was really operating like a director. Then I added directors and functional heads. Your job changes as you have people to replace those parts of the job that you were doing yourself before. 

Now I spend most of my time between the VP and CRO jobs…

Asad Zaman: How would you differentiate between VP and CRO in this context? 

Kyle Norton: The way that I've explained it in the past is your time horizon and level of abstraction go up as you as you get more and more senior and your team gets bigger.

For a VP its deliver the number no matter what happens. Deliver the number every single month, every single quarter, which takes forecasting, hiring, teaching and keeping the team accountable.

For a CRO it’s ensuring we are doing the things today that will enable us to hit the number a year, two or three down the line. I've spent a lot of 2025 thinking about 2026 and I'm already thinking about 2027 now. 2026 is pretty straightforward at this point because I've known what the plan was since the beginning of this year.

Generally, from a planning perspective we have three north stars and then two growth horizons. One of our growth horizons in 2025 was launching a point of sale. And so now this growth horizon is launched. We've got a team working on it. That's a core north star for 2026.  So we're always thinking about “these are the three main things and these are the two things that we're investing in for the future”. 

Asad Zaman: Is the POS business designed to give you more wallet share from customers in following years, so that you can maintain the growth you currently have in 2027, 2028, etc?

Kyle Norton: One of the northstars for next year is to double ARR in the core business. So we want to go from $65M to $135M and that's just the core business. And then we want to exit next year with hundreds of really happy point of sale customers. The financial goal is only $5M but I think I could build a $10M point of sale business next year. And then that $10 million point of sale business could be like a $50M point of sale business in 2027.

Asad Zaman: How much does seeing big numbers scare you? You’ve seen bigger numbers at Shopify before, hundreds of millions to billions. You have witnessed rapid growth back then as the market was hot. I assume you are less overwhelmed than people in a similar role like yours but without the experience. Do you agree?

Kyle Norton: I think your causality is inverted a little bit because I think they're scared because they don't have a plan or they're scared because they're not going in having built the foundations that they need. For example, it's November 17th and they get a financial plan from their CFO which says “you have to do X next year” and they freak out: “ I was just thinking about doing $3M this quarter and now I have to do $5.5M next quarter and $10M net new like in three quarters!” They haven't operated with those future years in mind. They're scared because they don't have a path. 

If people have a path, I don't think they're scared. I'm not scared because I'm like, "Oh, I just have to hire a bunch of reps and I have a CMO who's really good. He's going to scale some channels. We're building more redundancy in outbound and we're stretching to these mid-market customers. I just have a clear line of how to get to the number. Why would I be scared? It's just execution.

Asad Zaman: Do you think if you were a planner that’s never seen a big number, would that have ever been a factor? 

Kyle Norton: It definitely helps to have done this once before, but even then I only went $0 to $25M and now we're well more than double that. And I'm talking about a number that next year is like 7x or 8x that. So it's tough to say…maybe it’s  just my wiring that I'm overly optimistic and overly confident verging on arrogant.

Asad Zaman: That almost feels like a prerequisite for this type of role right? Did you always have this confidence as a revenue leader?

Kyle Norton: I don't think anybody would be like, "Oh, yeah. Kyle's the most humble guy." I genuinely went into this job being like, "I can build a company from early to IPO. I know I have what it takes. I just need the opportunity. I need the right product and the right team. I can do it." It's sort of an unhinged thing to say because there's only really been 5 or 10 people who have ever done it. When I say it, it seems ridiculous, but I absolutely believe it.

Asad Zaman: I think you're a good example of a person that definitely has an ego, but you're not a dick. People don't say you're a dick. No one ends up saying that. That’s the management of the ego. Your ego doesn't control you, but you have confidence. You have belief. You want to do things and you aren't afraid to say it and then go after it.

Kyle Norton: Because what's the alternative?

Asad Zaman: A mediocre life. The opposite is that you don't dream. You don't try. 

Kyle Norton: It’s the same thing like being an elite performer. You need optimism because if you're a pessimistic person, you're not going to take the bold bets you need. Just by virtue of me having the arrogance to think I can do it, means I'm going to place the bets that will do it. It doesn't mean it's going to happen. It could all blow up and I could hit the wall and they'll need to layer me or move me on. That's a reasonable outcome of this whole thing. But I'm still gonna operate like it's me and I'm gonna do it.

Asad Zaman: In all of our roles, I find that the most interesting thing is that as you are successful, there could come a time where you're no longer the right person. You have that at the back of your head. But then there's a little bit of like “well f*** that. I want to be the pattern breaker.”

I really like your framework of frontline manager, director, VP, CRO. As the company scales you basically get more and more time on the bottom two things (VP and CRO) and less time on the top two things (FLM and Director). How else is the job fundamentally different for you today? 

Kyle Norton: Time horizon is probably the number one thing and the size of the bets is number two. You need to operate with a degree of conviction that you're going to pivot a bunch of organizational resources into something that has a potentially significant payoff. There's a real material cost that comes with those things. When you're a VP of Sales managing eight reps directly, you're like “okay, we're going to go after this new type of customer” and you assign them a bunch of leads from this new sector. You can figure out in a couple weeks what the response rate is, so the stakes are very low. Over time, the stakes can get much much higher. 

One of the big bets for us this year was that I really put my neck on the line at the beginning of the year for a bunch of work and a bunch of money,  was the Toronto office project. My idea was: I'm going to bet that I can hire enough BDRs, SDRs and AEs in Toronto only. My whole recruiting strategy was I would post roles on LinkedIn and then we'd get 1600 applicants from everywhere. “Do I believe that there's enough positive impact from having BDRs in an office beside their manager to overcome the hiring difficulty and the cost of the office?” 

Asad Zaman: When you think of the bets getting bigger and the time horizons getting longer or further out, how does the communication between the stakeholders work?

Kyle Norton: You're definitely spending way more time in way more cross functional conversations. One of the biggest drains on my time right now is just cross functional alignment. Since things are so intertwined, the number of resources you need to do things is so much greater. There's a big tax on coordination. Sometimes these coordination efforts take more than 10% of my time. If I added up all the meetings that I have just doing alignment, I had seven meetings last week that had 20 people or more on it.

Asad Zaman: Do you think that having to work cross-functionally can be too steep a hurdle for people who haven’t experienced it before? They don't know how to make all these other people who are very different to the people they're used to dealing with feeling confident about them as the leader. The opinions of all these other people really matter at another scale, right? Do you think that plays out for people that get leveled up or get pushed in a negative way?

Kyle Norton: Yeah. Or they just don't spend the time and energy on it and, ultimately, that means they don't get things done and so they get criticized or looked down upon because they're not shipping things and they're just making excuses like missing a timeline because of product, enablement or rev ops. But I’d respond that it’s your job to get things done! Your job is to be able to align those resources and not consistently get surprised. I think that one of the hallmarks of somebody who's not going to scale is they are in reaction mode all the time and things are consistently surprising them and consistently seem unforeseen. You're always going to have unforeseen things but you should be trying to anticipate them.

Asad Zaman:  It almost feels like a constant state with some people. They never know how to get out of it.

Kyle Norton: And that's an okay state as a frontline manager, or maybe even somebody managing two managers because really you're just firefighting your way to the number every month and not a lot else matters. 

Asad Zaman: And some people I think are programmed to work really well under pressure. In school they write their assignment the night before. They study for the exam the night before. There are some people that I think are programmed like that. And so they do exceptionally well in these firefighting roles and then they move up because they're doing well and so they get more responsibility. But then when they get that next level of responsibility where they don't have the pressure today but  still have to think about this thing today, they have trouble with it. For you how much of it feels almost instinctive vs something you had to learn?

Kyle Norton: It's a really interesting question. I just try to learn as much as possible as fast as I can all the time. I'm just building the train tracks in front of myself as I'm going. And maybe I've built the train tracks 6 months ahead of myself. Maybe it's 18 months. Maybe it's 60 days. I don't know. I don't think you can know that definitively. All I know is that most of my career success I attribute to my learning motor. I just really like learning. You know I sent you my Spotify rap that one year. It was like 52,000 minutes of podcasts because I was trying to learn at that point something that was really podcast relevant and I was really into trying to absorb as much about the startup ecosystem as I could because I'd been out of it for three years. Recently, it was AI and I was just like binging everything AI on Twitter, YouTube, doing stuff with Jordan or just going to webinars. 

So I think that it's maybe not the right framing to say that I learnt these specific things to prepare for next year. I'm always just trying to learn as much as I can in general. Sometimes I'll have to go learn a specific skill set. It's like, "Oh s***, the world completely changed. Now I need to know about AI. AI is everything." And so I just did that. Now we're into this company building mode where it's a very different level of internal collaboration and coordination tax. And so I'm trying to learn from great people how they do this stuff. I've spent some time talking to Ashley Grech about this and we had this pavilion gold call where we talked about 2025 and 2026 planning. That's one venue for me…having people to text. One of the reasons I did the podcast was to build a crazy network of these people that I can text and call and talk shop with. Now I feel like I've got this insane network of people I can learn from.

Asad Zaman: You seem to be levelheaded and calm most of the time. You don't get rattled and overly anxious. How much does that matter to you? How much value do you give the routines and habits that you've developed to be able to manage your nervous system?

Kyle Norton: Massively. I don't think you can do any of these jobs if you're a nervous wreck. We all have some level of brokenness. I think everybody who does these jobs has some level of dysfunction. We have some hole within ourselves that we're trying to fill through performing well at this thing that we can be measured against, but you absolutely need to have the right engine for it. So sleeping and eating are important; I work out every day. The one point where I was sort of coming off the rails was early in my VP career and things were going sideways and my boss was a crazy nightmare. I was so stressed and had a hard time sleeping. So I worked with an exec coach and I did the “search inside yourself” course from Google. That really helped me build this foundation. That was 10 years ago now. I still take those skills with me every single day. 

You almost never want to be high adrenaline. When you look at neuroscience,  your cortisol and adrenaline are raised, your blood supply goes to your fight or flight system, i.e. your heart, lungs, legs and arms and the place the blood comes from is your brain. According to physiology research, your brain is at a -15% position when you are in a fight or flight state, which isn’t conducive for the work a CRO needs to do.

Asad Zaman: Another thing that enables or holds a CRO from scaling through stages is their team. Everything in business is downstream of the intelligence and capabilities of the people that we hire in the team, right? How do you think about this? 

Kyle Norton: Transparency and honesty are sort of the building blocks. The conversation that everybody avoids, that is the most important one, is “do you think this person is the right person to scale you from X  to X times 2”. The worst case scenario is you let that person go way too long. They have a miserable last six months in this role. You as the leader are spending a bunch of your time trying to do their job for them or with them. Everybody's miserable and you look like an idiot because you didn't make the hard decision which is “hey, somebody else is needed there”. 

The thing that I preach is having an open and honest conversation about it and thinking about your relationship in a longer time horizon than just in that company together. You might have somebody who was awesome to get you from $5M to $25M in ARR and that was successful for them and they vested most of their equity. Yet you don't think that they have what it takes to be a $25M to $50M person. You have to be able to say, "Hey, look, like I need to bring in somebody above you and then you're going to learn a bunch from them or I need to bring somebody else in. So, let's figure out where you do want to land. Let me help you land in that next place." That's a very different conversation. Then you can play an active role in that person's next career steps and ultimately you guys might come back together at some future point. I have a bunch of people on my team that have worked for me in the past in different places.

Asad Zaman: This has been great! Last question..what was some naivety that you had in the early part of your career that you think helped you get where you are today?

Kyle Norton: Just like believing I can do it for sure. Just being like, "Oh yeah, I can absolutely do that. I can be a VP of sales." When I got my first shot I was like “dude, I can be a VP of sales, no problem”.

Asad Zaman: Have you ever not had it? Has there been a point in your life where you were unsure about yourself or in a fight where you were thinking, what am I doing here? 

Kyle Norton: With the martial arts academy (Kyle competed in martial arts at a really high level, and owned a martial arts academy too), I noticed that this was not working and I don't want to fix it because the returns on the leverage are so bad. I was just like I'm not doing a good job right now and actually I think doing it really is not worth it.

Asad Zaman: Do you think this almost naive self-belief can be quite helpful.

Kyle Norton: I very much believe that. Michael Gervais said this on my podcast: I’ve never seen an elite performer that wasn’t inherently optimistic. You have to be optimistic about yourself.

Asad Zaman: And about the world a little bit.

Kyle Norton: And about the world, for sure.

One of the most common questions GTM executives ask me, especially sales leaders, is how to convince a skeptical CEO. The debate is usually about unrealistic growth targets. It often starts when a leader takes a class on unit economics or P&L fluency, runs the numbers on their 2026 plan, and realizes they have no chance in hell of hitting it.

The worst move is getting emotional. CEOs have very little patience for the sales leader who looks frustrated all the time. Instead, you need to do two things: use objective data and make the CEO feel like whatever you want them to believe was their idea. It’s called inception and it’s not just a movie starring Leo DiCaprio.

The cleanest way to convince a CEO is to present a clear set of objective business measurements, calculate the implied growth ratios together, then look at them calmly and ask, “What conclusion would you draw from this data?” It’s hard to change a CEO’s mind, but this is your safest bet.

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