How to scale GTM from 
$2M – $20M ARR in 2 years: CRO Kyle Norton

Scaling SMB Vertical SaaS Owner from $2M to $30M with an Ever Evolving Playbook that Adapts Sales Strategy at Each Milestone: CRO Kyle Norton 

The secret to the best Sales Playbook for scaling is that it changes at each stage. Kyle Norton took his company from $2M to $30M ARR in just a few years by pivoting the GTM strategy to the challenge at hand. Kyle offers actionable advice for Sales Leaders and Founders in early stages on: 

• The right criteria for hiring early growers vs hiring at scale  
• Assessing a company’s growth potential before joining  
• Early investments in RevOps to scale faster 
• Preparing for setbacks before they happen 

You’ll hear everything a Founder needs to know to find the right Sales Leader to take them to $30M — from a Sales Leader who has done it. With guest Kyle Norton and Bravado CEO Sahil Mansuri.

Time-coded show notes:

4:35 — Doing hard things helped me be better at Sales

5:45 — Finding a winning company 

17:30 — What to look for in a founding team 

35:00 — Your first VP of Sales is a bridge 

49:40 — You need Pirates and Romantics 

59:00 — In office vs remote 

1:10:00 — Shoot above your number 

1:13:30 — Quick fire round

Full transcript:

00:00:00:00 - 00:00:20:22
Kyle Norton: You have to make bold bets even when things are going well, or else at some point growth slows and and I intend on growth being faster in 2025 than it was in 2020. For your finance team or the board, like, make your own determination of what's possible and don't go shoot for the number. Go shoot for what? What's possible.

00:00:20:22 - 00:00:25:12
Kyle Norton: If I could really, like, run the table. Like then where? Where do we end up?

00:00:30:18 - 00:00:56:19
Sahil Mansuri: Hi everyone. Welcome to the Bravado Podcast. Our goal here with the Bravado Podcast is to find the crow's feet, the sail sales leaders who are building legendary companies and sales teams and pick their brain, go super deep with them. In terms of the people, the process, the tools, so that you yourself can adopt a lot of their learnings and take your company from where you are today to where you're trying to go.

00:00:56:21 - 00:01:11:02
Sahil Mansuri: And joining me today is the legendary crew of owner recon Kyle Norton Previously led, sales at Shopify. Kyle, welcome to the Bravado Pod, man. So excited to have you.

00:01:11:04 - 00:01:13:05
Kyle Norton: Yeah, thanks for having me. I'm excited for this one. Yeah.

00:01:13:05 - 00:01:25:01
Sahil Mansuri: This is going to be a lot of fun. I want to start off with, a quick thing, which is that I saw that you had a background in martial arts. Maybe you could share a little bit about that and be super interested to hear.

00:01:25:03 - 00:01:56:07
Kyle Norton: Yeah. So when I was 17, I think like many sort of the early days of the US, UFC just was in enthralled with that as a sport and especially, you know, watching Royce Gracie, who was a Brazilian jiu jitsu guy. 160 pounds, tapping out like massive behemoths, dudes and boxers and wrestlers and all this stuff and, sort of tiptoed my way into like, oh, maybe I'll learn a little bit about this Brazilian jiu jitsu thing.

00:01:56:07 - 00:02:14:06
Kyle Norton: And I signed up for like a two day a week pass. Then like two weeks in, I'm like, hey, I actually want to do four days a week. And then the next week I was adding boxing and wrestling. And by the end of that summer, I was training like three hours a day, six days a week. And it became like the only thing I cared about for the better part of eight years.

00:02:14:08 - 00:02:37:06
Kyle Norton: And so, like, I went down to train and compete in Brazil with our top team there. I competed a bunch locally. I, co-owned for a long time a mixed martial arts academy that I started with my coach at the time. So it was definitely like an obsession of mine. And I give it, I give martial arts a lot of credit for who I became as a business leader.

00:02:37:07 - 00:03:03:09
Kyle Norton: Just because you learn like an it pretty incredible resilience. And, you learn how to learn because it's so like tactical, like you learning and getting better faster means you don't get beat up. So much. So there's a very, very like tactical feedback loop then. So a lot of how I teach sales today is built in some of that learning methodology that I learned in martial arts.

00:03:03:10 - 00:03:24:13
Sahil Mansuri: They say that, you know, sales is all about getting punched in the face and getting back up. And, you know, it seems like you've got a, really strong perspective on doing that, literally. Yeah, that you're able to bring that figuratively to, to your, to your sales teams. How did you end up getting from martial arts into SAS?

00:03:24:15 - 00:03:43:03
Kyle Norton: Like most people, I just fell into it. At a college, there was an events company that hired out of our business program, and it was like one of the very few sales roles that were available. And, a woman who graduated a year ahead of me was at this company and made like a hundred grand in her first year and was getting promoted to manager.

00:03:43:03 - 00:04:07:16
Kyle Norton: I was like, that's what I want, I just wanted I wanted a job where my, accomplishments and success would determine my trajectory. And, you know, most of my schoolmates who went into consulting and banking and, CPG marketing, like, you know, that was a very fixed roadmap of how fast you could progress. And just the the meritocracy of sales spoke to me.

00:04:07:18 - 00:04:40:17
Kyle Norton: So I just, you know, like randomly stumbled into it. And then I was with I was there for 4 or 5 years. Boiler room type environment. You know, like cold calling 150, 200 miles a day type of thing and learned a lot of the like really, really core skills of persuasion. It was awesome. And then eventually graduated into other stuff, like a cold called my way into my first tech job, actually cold called Mark Bergen, who was, the EVP, Sales and Vision Critical and then ran revenue at Shopify later, bro.

00:04:40:19 - 00:05:04:06
Kyle Norton: So I tagged along with him there. And cold called him for that job because my resume wasn't super compelling. Like, I was a second line leader at this, like, shitty events company. But I knew how to sell. I just needed to prove that to somebody in in through the cold call in a conversation, then, broke my way into tech, where I ran a global BTR team for a little while there.

00:05:04:10 - 00:05:32:00
Sahil Mansuri: You want to talk a little bit about, your. One of the things you and I have talked about is, you know, a lot of times, as a sales person, you can spend so much effort and energy selling a really shitty product at a shitty company and getting nowhere, and that if you join a really great company with a really great product and maybe even only work 75% or 80% is hard, you can still get much more in terms of results and quota and whatnot.

00:05:32:06 - 00:05:57:15
Sahil Mansuri: And then the the magic intersection of great product meets a great work ethic and ability is where the really amazing stuff happens. I would love to hear your perspective on like, selling a shitty events product and then moving into selling Shopify. And now owner and what you've learned and what you might advise someone who is starting out in terms of how important is it to pick the right company in the right product versus just getting a role in.

00:05:57:15 - 00:06:15:03
Kyle Norton: It's interesting because I think a lot of the success I've had in my career is because I started with a pretty crappy product, you know, like when you were calling, customers who had come to our events previously like, no, no, that wasn't very good. Like, don't call me again. Like, that was the quality of the product we were selling.

00:06:15:05 - 00:06:44:05
Kyle Norton: And so you really had to learn how to, sell around that and spin and, and, you know, we probably took it too far, to be honest, like, well, you could sell anything or you could say anything to, to get a deal. Then, but doing the hard thing was actually really formative for me. And, and yet, you know, like, I couldn't have I wouldn't have had the career trajectory that I've had now if I had kept in this sort of market.

00:06:44:07 - 00:07:07:09
Kyle Norton: And so I think in an early career, you just want to optimize for leadership, like there was a lot of really great salespeople at that company. And I learned the craft from awesome sales, salespeople like the managers and directors there were were awesome. So while I didn't have a good product, I had a great learning environment and I had great, great leaders to learn from.

00:07:07:09 - 00:07:36:22
Kyle Norton: And so I would say, like, that's the thing to optimize for early in a career. But then, yeah, at some point you want to hit your wagon to a winner. And in especially if you're in leadership like it's way more important in your first manager or second line leadership position. If you're not in a great company, you're cooked like, no, no amount of sales heroics can get you around, out of control churn and a poor performing product.

00:07:37:00 - 00:07:58:08
Kyle Norton: I see this a lot to folks. Like, you're way better off being the number two person at a number one company versus being the number one person at, like, a number seven company. And you see people make this mistake, like over and over and over a cycle, my first VP sales job. And then you look at the founders and you look at the product and you look at the the market.

00:07:58:08 - 00:08:26:09
Kyle Norton: And investors are like, this is DOA. And now you got your first VP sales or first VP sales job, but you're probably going to be out in nine months or 14 months, and it might actually look like a sort of a poor mark on your resume. And so you're better off to go hitch your wagon to like, somebody awesome, who's a great leader with a winning product and be the number two, because, you know, you're the VP of sales at some crappy company.

00:08:26:15 - 00:08:49:10
Kyle Norton: You're really just a glorified manager. You're you're managing for reps versus you're the number two for a great CRO. You might have four managers under you and 40 reps like who's more senior direct to at the good company or VP at the crappy company. You know, it's it's easy to let vanity, make you make the wrong decisions there.

00:08:49:12 - 00:09:16:07
Sahil Mansuri: There's so much goodness to that. But the one, the one thing I, I want to call out is up front, which I think is lost on a lot of founders when they're looking to hire a sales leader, is how critical it is that that person has sold a shitty product before. I see so many sales leaders who, like, got their first job at Salesforce and then went to stripe and then went, you know, Google and then now join a series, A company.

00:09:16:09 - 00:09:42:21
Sahil Mansuri: And when that happens, it they really struggle. Because if you've never, you know, my first sales job at meltwater, this is this is not just great. We had 1000 people at the company when I joined. 960 were in sales. So we had 40 people for everything else. Like, I don't even know who built the product. I'm not sure that we had more than five engineers in the company.

00:09:42:21 - 00:10:04:20
Sahil Mansuri: I'm not joking. Like, this goes crazy. This company was basically selling the shittiest product on the planet and, and and now they've made a lot more investments. The company is much better. But like back in 2008, 2009, I this company was a disaster. And it was the same thing where you I mean, you couldn't rely on there was zero inbound.

00:10:04:20 - 00:10:29:21
Sahil Mansuri: There was the most common response you got when you talk to somebody who had heard of meltwater. Is this product's a piece of shit. I would never buy it. So you had to, like, be really, really, really resourceful in order to try to get deals done and then after spending two and a half years there where, you know, I grew to be the number one rep in the company, I got to Glassdoor and when I got to Glassdoor, the product was amazing.

00:10:29:21 - 00:10:31:16
Sahil Mansuri: We had insane product market fit.

00:10:31:16 - 00:10:32:08
Kyle Norton: So fun.

00:10:32:08 - 00:10:53:01
Sahil Mansuri: And it was. And I was like, wait a minute, this is what sales is supposed to be like. And I very quickly became the number one rep at Glassdoor because it was just so much easier to sell. And I had so much experience in like the psychology of sales and tactics of sales, because nothing ever went our way about water, that I knew how to make something from nothing.

00:10:53:04 - 00:11:11:12
Sahil Mansuri: That when you gave me a huge advantage, I was able to capitalize on it really quickly. And I and I think that the inverse of that, which is that if you only know how to take something that's great and sell it, and then you walk into an early stage company where many things go wrong, all the time, you get stopped a lot, we call it, you know, getting stopped.

00:11:11:13 - 00:11:27:21
Sahil Mansuri: How quickly do you get stopped as a as a leader, as a rep. And I think it's just such a it's such an important point that if you've never faced real adversity with the quality of the product that you sold, that you don't actually really know what it takes in order to sell at an early stage. I feel very strongly about that.

00:11:28:01 - 00:11:28:12
Sahil Mansuri: Yeah.

00:11:28:12 - 00:11:49:20
Kyle Norton: And and these are good guidelines. And I think especially for the founders listening, that doesn't mean that no one from good companies will be good because there's, you know, plenty of examples of people that have been at Salesforce for a decade that do have success when they go into a startup. But, you need to dig into the DNA.

00:11:49:21 - 00:12:10:07
Kyle Norton: I think all too often in hiring, we revert to superficial indicators. And this could be the reverse. It could be like, oh, they were at Salesforce, they must be awesome. And so you hire them and they're not awesome. Or it could be the opposite. Hey, you know, this person's only sold great products so they can't they couldn't possibly be good in a startup.

00:12:10:09 - 00:12:32:21
Kyle Norton: Well, that's not true either. But they are indicators of what to dig into in an interview process. And really, what you're trying to get to is like the horror foundation of all of the competencies you need in that role. And so, you know, the challenge hiring somebody from Shopify, because when my people cold call to Shopify, hey, it's Kyle from Shopify.

00:12:33:01 - 00:12:55:09
Kyle Norton: Hey, how are you doing? People like excited to hear from us. And what's slick the weirdest thing I like I like couldn't like it. Just like baffled me as somebody who had never sold a great product before, until shop and, what you're looking for is, is the DNA of of do they understand the science of persuasion?

00:12:55:09 - 00:13:19:06
Kyle Norton: Do they have grit and resilience? You know, they've had a good product to sell with name recognition. Have they demonstrated the, the, the things that underlie sort of that superficial, layer at the top? And I think that's where founders go wrong is, is they, they on both sides of this coin, they're like, oh, they went to Stanford and they were at this fancy company.

00:13:19:06 - 00:13:41:02
Kyle Norton: They must be awesome. But they've never had to solve problems on their own from first principles, because they were a second line leader at a massive company, and they never took the initiative to go take on a big project. And and like, you know, I was a leader at Shopify, a big company, on paper. But I had my hands in everything.

00:13:41:02 - 00:13:56:11
Kyle Norton: Like you, we were rerunning our global sales positioning. So I'm like, hey, let me be the revenue sponsor on that. And, and then we were looking at comp. And so I was like deep into all of this comp stuff. And so even though I was at a big company, I was still like deeply problem solving. But you didn't need to.

00:13:56:11 - 00:14:18:05
Kyle Norton: There was other people in my similar seat that, like, weren't going to go take on those like gnarly, complex things. And so that my advice to founders is like dig, like dig under the surface to get to what you really think is important in your job, and know what you're like, what is your jobs to be done framework?

00:14:18:05 - 00:14:28:05
Kyle Norton: What are the competencies you're hiring for? What are the specific skills, and then what are the characteristics like what are the values. How do you how do you intend on running the company and like get to that?

00:14:28:05 - 00:14:54:13
Sahil Mansuri: We're on the topic pretty deeply now of what should a founder look for when they're looking to bring in early stage leader? I just I know this is well known, kind of, you know, in many circles, but just for the, you know, couple people that have been living under a rock, maybe you could just describe, you know, at what stage you joined owner like roughly in terms of revenue, size of, sales team, you know, people, etc., and roughly what stage you're at now.

00:14:54:14 - 00:15:17:06
Sahil Mansuri: I honestly don't need specifics, but just roughly, you know, about revenue, about sales, team size, etc., so that we can get some context around that. And then I want to go really deep for a few minutes on what founders who are at that first stage of where owner was when you joined, which are many companies, obviously, what they should be looking for in hiring their own Kyle Naughton.

00:15:17:06 - 00:15:20:06
Sahil Mansuri: So maybe just give us some context first and then we'll and then we'll dig in.

00:15:20:06 - 00:15:56:16
Kyle Norton: I joined owner in June 2022. They were two and Change millionaire at the time. And I inherited a manager and four reps. Two of the reps weren't a fit. We parted ways pretty quickly and then we sort of rebuilt from there. All three of those, the manager and the two reps that, I kept are still with the company today and and actually crushing, now we're right around 30 million RR the sales team as of, like, Monday is going to be about 60 people.

00:15:56:18 - 00:16:12:07
Kyle Norton: And I have the onboarding function as well. Rep ops enablement partnerships and BD, and whatever else is sort of like related. Yeah. So that's the journey.

00:16:12:08 - 00:16:31:10
Sahil Mansuri: Okay. So let's go back to one like frontline manager, 2 to 4 reps 2 million and RR and change. So that's a pretty unproven product. And a pretty early as far as early goes. That's pretty early. It's it's early.

00:16:31:12 - 00:16:36:00
Kyle Norton: It's so early that I said I would never go back to a company this early before I took this job.

00:16:36:02 - 00:16:52:09
Sahil Mansuri: Okay. I want to dig into that in just a second. But before we do that, let's let me ask the primary question, which is, so what made you join owner and what, you know, what was owner CEO looking for at the time, and how did you guys find a match there?

00:16:52:09 - 00:17:20:23
Kyle Norton: I look at joining a company the same way that a venture capital investor looks at making an investment. It's team product market, and it's sort of the allocation of importance to those three things that basically separate most VCs I am in the camp of. It's like 70% team. And really when I say team, that's just founders, like almost everybody else is going to come and go, you know, as hard as that is sometimes to admit.

00:17:20:23 - 00:17:51:18
Kyle Norton: And there's lots of people who stay for a long time, but the the caliber of the co-founders determines basically everything after that, the, the quality of people they can attract, their ability to fundraise, the culture that set the sort of environment. And then, yeah, you want to opt for a big market or a company that's in a market that could become a big market, you know, like when Shopify was founded, e-commerce was a tiny market, but obviously has become something very different.

00:17:51:20 - 00:18:17:06
Kyle Norton: And then product quality. And so like at that stage you're creating on a curve. But is this a good product and is it getting better fast? And those three things were very much there in, in owner I. So I'm a part of I'm an in GTM fund. They invested in owner. I was a part of the process to get GTM fund into that deal.

00:18:17:08 - 00:18:34:11
Kyle Norton: Basically like Scott who you and I both know well, Scott Barker was like, hey, you know, we got this deal. It's shit hot. We like absolutely want into it. So I need you to get I got on the call with the founder. He's like, this is not a diligence call. He's like, I don't need diligence because it's sort of owners like Shopify for restaurants.

00:18:34:11 - 00:19:00:10
Kyle Norton: And I was at Shopify. He's like, I don't need you to tell me if you like it or not. Like just you're in full sell mode. Convinced this founder that taking our money is great because he'll get access to people like you. So I, I've done with Adam, and I was just, like, insanely impressed. And the the my model for founders, when I think about taking on advisory or or cutting checks is basically like, are they a force of nature?

00:19:00:15 - 00:19:17:06
Kyle Norton: So do they have like, will in a, like an unnatural will and drive and resist the resilience and can and do like when you're on a call with them, do you leave, do you leave with like, a sense of awe? So that's like number one force of nature. Number two is are they a learning machine?

00:19:17:08 - 00:19:52:16
Kyle Norton: And I remember on my first or second call, Adam, I, I recommended this book. I'm like, oh yeah, I actually like this I like this book on positioning. It's called Made to Stick. And he's like, oh, cool, I'll pick that up. And then 18 hours later he texts me. He's like, hey, I read that book you mentioned. And, he had like all these questions, not clarifying questions or help me understand, like, really nuanced, like detailed questions that require a level of sort of understanding and insight that, that I totally didn't expect from, like an early stage founder that doesn't have a sales background.

00:19:52:18 - 00:20:22:07
Kyle Norton: So Learning Machine is is the second piece. The third piece is founder Market fit. Like, is there some reason why this founder has the upper should have the right to win in this market? And Adam basically started this business for his mom and was deeply passionate about it. And then the fourth thing which is often missing is do they have enough humility not to blow up, blow it all up, because there's a lot of founders who are incredibly smart super learners, and they're a force of nature.

00:20:22:09 - 00:20:41:04
Kyle Norton: The Venn diagram of that person also having an overlay with the humility, circle is like pretty rare. But then you find those people hit a wall at some point because they won't listen to their investors, they won't listen to advisors, they won't listen to their their C-suite, and they just sort of drive the thing into the wall.

00:20:41:06 - 00:21:00:00
Kyle Norton: And so that is what I saw in the two co-founders, Adam and Dean. And I was super happy with Shopify, and the timing couldn't have been worse for me to leave. I just had my second kid. Like, things are good. I love Shopify as a company, like I still am. Like the big I haven't sold a share.

00:21:00:02 - 00:21:14:12
Kyle Norton: Like I'm a I'm a massive fan. But I just could not not take this opportunity because I thought I might regret it for basically the rest of my career. Just watching them rip on LinkedIn and knowing I could have been a part of the journey.

00:21:14:12 - 00:21:39:10
Sahil Mansuri: Okay, that was that was amazing. And we're going to take a lot of what you just said and turn it into like a little infographic of like, Criteo. I love the Venn diagram. I love your description. Not just the categories, but your description of how to assess for those things, because I think it's pretty well known that, like, you know, you want to join an awesome founder, but like, what makes for an awesome founder and you want to join a product that's that that's great.

00:21:39:10 - 00:21:57:11
Sahil Mansuri: But like at that stage, most products aren't that great. And so like, how do you think about that? Your idea around founder Market fit? I really enjoy it. Like as well. The only thing I'd add to it is the quality of investor that's backed. The company I think also makes a really big difference. It can. It's a sure a you know, when I was considering Glassdoor, I had two other offers.

00:21:57:16 - 00:22:22:07
Sahil Mansuri: And both of the offers were it's funny. Yeah. So some of our we've we've, we've lived parallel lives in some in some way. So I had the opportunity to go be the number one, to shitty companies. I didn't know they were shitty because I was 24 years old. I didn't know anything, but, I had the opportunity to be the number one, to, you know, like, less well-established companies or to be the number two, Glassdoor.

00:22:22:09 - 00:22:52:20
Sahil Mansuri: And I was leading towards I actually initially said no to Gloucester's offer because I wanted the VP sales title. I wanted the, you know, three. It's the three quarter point equity that came with it. Gloucester was offering me a very, very small fraction of that. And so I said no. And the CEO, Bob Homan, who really liked me in the interview and thought that I had some potential but was obviously like confused as all heck as to how to make this decision, wrote me this legendary email on like Sunday night.

00:22:52:20 - 00:23:08:09
Sahil Mansuri: He basically, he and I were you. I rejected his offer. And then he wrote me back to try to get me to reconsider and come in. And I said, no, I'd already made my decision that I wanted a VP title or whatnot, but he basically broke down for me how I should be thinking about evaluating a startup.

00:23:08:13 - 00:23:31:18
Sahil Mansuri: And for context, Bob was, you know, an early employee at Microsoft had built a really successful business with Rich Barton around Zillow and had had built, it just I mean, he was he was, you know, he was a very, very successful CEO before joining or founding Glassdoor. And he basically broke down. He's like got benchmark backed Glassdoor, like benchmark does eight deals a year.

00:23:31:18 - 00:23:54:02
Sahil Mansuri: They are one of the like most Premier. Yeah yeah VCs. And Rich Barton is on our board. He's like one of the top ten most respected venture capitalists. Like these things matter in terms of future access to capital and trajectory of the company and whatever. And he and he was like, you're not. He goes a three fourths of a point of nothing is still nothing, you know?

00:23:54:02 - 00:24:16:03
Sahil Mansuri: But here I think they had offered me. I if I remember correctly, it was like .02 percent of the company is what it was. So I was basically getting like the 1/34 or whatever of the offer that I was getting from. These are 130 7.5 of the offer that I was getting from these other, he was like, is, is is going to it could be worth a lot more.

00:24:16:03 - 00:24:36:20
Sahil Mansuri: And he tried to help me understand and assess it, which the fact that he took the time to do that, you know, given the fact that I was, you know, not that special of a of an employee was spoke a lot about it as well. But I ended up meeting him back in person, talking about it. And then I was he told me I was the only sales person that he had ever interviewed who negotiated purely on equity.

00:24:36:20 - 00:25:14:03
Sahil Mansuri: I didn't care about the base. I didn't care about the commission. I only cared about the equity, because I had figured out somewhere along the line that the only thing that mattered was getting a big enough portion of the pie of the equity of the company, that if the thing worked out, that that it would matter. And I ended up actually taking a lower base, lower kind of smaller commission plan, obviously uncapped, but but but lower percentage in order to get a much larger equity stake in Glassdoor, which when Glassdoor got acquired for $1.2 billion, meant that I had the opportunity to pay off my parents, like, you know, help my parents with their, their

00:25:14:03 - 00:25:38:15
Sahil Mansuri: stuff and then and then have the opportunity to found to find bravado. So I wouldn't have ever had the opportunity to even start this company, because I wasn't in the financial position where I could take risks like that without that exit from Glassdoor and so it's a very long winded way of getting to a simple point, which is like assessing the right company and picking the right winner can change the trajectory of your career, of your life.

00:25:38:17 - 00:25:42:20
Sahil Mansuri: As a as it has for you, I'm sure, and it's just really, really meaningful.

00:25:43:01 - 00:26:15:10
Kyle Norton: Absolutely. I think like the caliber of investors is important. And like, Jason Lumpkin is on the board here, who I've followed since, like, the earliest days of my tech sales career and have a tremendous amount respect. And it's redpoint and it's Jack Altman, like really, really savvy folks that, I respected. I the one thing I caution is to like, be careful of reasoning by analogy, because I see this all the time and in similar to like don't just don't just look at the resume like try to get to what's underneath.

00:26:15:12 - 00:26:47:16
Kyle Norton: The investors are really important, but you want to do your own diligence to understand, okay, they have seen these three things, team product market. But like, do your own diligence on that to make sure that what they saw is still there, because potentially you have another 12 months of data that didn't exist. Like maybe Andreessen did the seed, maybe Redpoint did the A, but now you're 12 months in and there's much more data to make that decision off of.

00:26:47:18 - 00:27:12:12
Kyle Norton: And you can know whether or not the market is, like, really viable. You can know whether or not the product has the traction that you, that you originally thought. Because when you're joining a two or a $4 million company, like, there is still tremendous risk there. And so you want to be careful of of not only reasoning by analogy and using those as indicators, as important indicators, but then doing your own diligence to dig, dig in.

00:27:12:12 - 00:27:33:03
Kyle Norton: And so when I say team product market, you know, I talked about my founder model, but then on product like ask the questions about viability. What's the churn rate? What is the what is the Nar like? Is is revenue with your customer base growing or contracting? Who are you losing deals to? What are your top? What are your top churn reasons?

00:27:33:03 - 00:27:50:04
Kyle Norton: What are your top close loss reasons? Like, there's a lot of ways to get product fidelity and nobody does that. And when I was interviewing with owner, I sat down with the CFO and he pulled up the spreadsheet of, like the entire growth model, historical numbers and projections. And we we went through it like line by line. Okay.

00:27:50:04 - 00:28:13:12
Kyle Norton: Tell me about this. What about this assumption? You have this going from X to Y. Like how do you what's the plan to get there. And that that is like a very important trust or, confidence building exercise for a potential revenue leader to do because you're this is more important than an investment. This is more important. You know, like benchmark who doesn't write a lot of checks.

00:28:13:12 - 00:28:34:15
Kyle Norton: They write a handful a year. You write one of you make one of these decisions every like two to 4 to 10 years. So so arguably your diligence, your company diligence should be quadruple what an an what a venture capital investor does what who what revenue leaders are doing that level of diligence like, almost none.

00:28:34:17 - 00:28:54:19
Sahil Mansuri: Yeah. Very very very few. And I love your point around the basket approach that a VC takes versus you only get one career and you're investing something far, far more important than, than than money, which is your time. And you know, you there's there's no there's no second, there's, there's no take backs on that. And you can only.

00:28:54:19 - 00:29:15:18
Kyle Norton: Make a couple wrong choices before people start questioning your resume. If you have if you have two nine month stints, two nine month VP sales stints, I would I will personally judge that. I'll be like, I don't know, like either they have no business acumen because they don't know how to pick companies. And that's a concern I need.

00:29:15:18 - 00:29:22:21
Kyle Norton: I need people with business acumen or they're bad at their job. So, you have to be really joyful about it.

00:29:22:23 - 00:29:51:11
Sahil Mansuri: I couldn't agree more. What about the other side, Kyle? So now let's talk about the. You know, what Adam was looking for. Or maybe. Maybe I'll ask the question this way, which is, you know, if you were advising, which I'm sure you do, founders of companies that are between the 1 to 3 million have a couple sales reps kind of stage, and now they're thinking, okay, I want to bring in, head of sales, a VP of sales, in order to take this thing from 2 to 20.

00:29:51:17 - 00:30:08:16
Sahil Mansuri: What are the heuristics? What are the criteria? What are the things that you would want to spend some, some time evaluating, understand doing both on a resume for initial screening, in conversations that you think leads to, the best possible chance of success.

00:30:08:16 - 00:30:26:17
Kyle Norton: So I definitely spend a bunch of time on this. You and I both advise the company who I've helped place a head of sales at who's doing amazing. And so that this is the framework that I give them. So they need to be really considered about like, what are the specific jobs to be done of this, this role.

00:30:26:18 - 00:30:45:18
Kyle Norton: And you can't be generic, can't be like acquire customers and like grow revenue. No, no. Like what are the specific things that this individual needs to do? Because in an enterprise environment, those jobs to be done are going to be quite different than in an SMB environment. In enterprise, they have to be on the road every week with their reps closing deals.

00:30:45:18 - 00:31:03:03
Kyle Norton: They need to be like the super duper rep, and, they're going to play that role for quite a long time. Look at that league. I played that role for three straight years. I was in all of the biggest deals. I was on the road constantly because we were selling enterprise versus the jobs to be done for. My role at owner were quite different.

00:31:03:05 - 00:31:36:22
Kyle Norton: I was never on the road. We sell completely digitally and it's all about infrastructure and systems, building and building stuff. That's repeatable and scalable. And so you and every, every founder should read the book. Who? I've stolen a lot of how I think about, hiring from from this book. And one of the things that who talks a lot about is just like the importance of scorecard, the importance of, sitting down and thinking very considerately, like, what are the jobs to be done?

00:31:36:22 - 00:32:02:11
Kyle Norton: What are the competencies I need to screen for? And then what are the experiences that that I'm I'm looking for that indicate they can do that. And so it's this is the model. It's, jobs to be done one competencies and skills. Number two. So what are the specific things that you're looking for. Evidence. Evidence of values in DNA is is three.

00:32:02:11 - 00:32:24:21
Kyle Norton: So they have to want to run their team in a way that's congruent with how you want to run a team. And when there's incongruent see like it. No matter what you do, it won't work. If you are a top down authoritarian and this person is like a bottoms up and in like empowerment, engagement leader, like it's it's not going to be it's not going to be a good fit.

00:32:24:23 - 00:32:49:12
Kyle Norton: And then the final thing is you just have to consistently validate, test for performance, like you want to find a history of excellence, like, is this person great at what they do? And so, the common pitfalls is again, like reasoning by analogy, it's, it's saying like, oh, I want a sales leader. So I'm going to go hire somebody who is a senior person at like at a big company that's similar to mine.

00:32:49:16 - 00:33:11:17
Kyle Norton: Well, the, the jobs to be done there as a second or third line leader at Oracle or some mega company are like very, very different than the jobs to be done at a small company, at a big company, one of your main jobs as a senior leader is just like internal politics and fighting for what your team needs and getting deals approved and having, procurements sign off on stuff like that.

00:33:11:18 - 00:33:33:12
Kyle Norton: That is the reality of that job. It's very challenging and it's a different set of skills. And I had to learn very different things to be successful at Shopify than I apply as a startup leader. But like, so what are the jobs to be done? And you really carefully assessing that that it's there in the candidate then like the real skills and the skills needs to be applicable to your market.

00:33:33:14 - 00:34:16:02
Kyle Norton: So they need to be stage appropriate, customer appropriate and deal size appropriate. So you can take somebody from a stage or two away from your current company. So if you're at 5 million, if there's like a stage of 1 to 10, so there's 0 to 1, 1 to 10, ten to like 25, 25, maybe to 75. And then there's like real scale at 75 plus, like you can if you're at the $10 million mark, you can go, you can go grab somebody who's who's done it at like a $75 million company that you're still in the range because they probably saw they were probably there when it was only like 17 or 20 million.

00:34:16:04 - 00:34:18:16
Kyle Norton: I can pull people people down. Yeah.

00:34:18:19 - 00:34:24:05
Sahil Mansuri: But if you're but if you're looking for some way, if you're at like two or 1 or 3 or something like that.

00:34:24:07 - 00:34:54:08
Kyle Norton: You're really looking for, a bridge. And so this is the hard thing to understand for sales leaders. And I think, this is the advice I give to founders. And, it feels like I'm doing a disservice to, to sales leaders, but I think we should be honest about both sides of the equation. Most of the for most companies, the sales leaders you hire at like 1 to 3 million, you're really just trying to get a person to get you through the next 24 months.

00:34:54:10 - 00:35:13:09
Kyle Norton: And either that person scales in a way and learns and grows in a way that is pretty remarkable and rare and then they can be keeping your VP, sales or CRO, or you're going to layer that person with somebody who's seen the next parts of their journey. And both founder and revenue leader should see that as a success.

00:35:13:11 - 00:35:33:18
Kyle Norton: Should should see that as like a a massive win. And you're going to keep your equity. You're still going to have the equity of an early stage of sales, which will be quite meaningful. And you're going to get to now learn from somebody who's been there and done that and can help you become the person that then can be that person the next time.

00:35:33:18 - 00:35:54:15
Kyle Norton: And I think, you know, again, this comes back to sort of like vanity and ego. Many in Lemkin talked about this on, on my podcast with him, and he talks about this a bunch externally. Like how are you react to getting layered is, is like very is very telling. But a founder should just be honest.

00:35:54:15 - 00:36:16:12
Kyle Norton: It's like, hey, look, success here looks success. You're it looks like you're getting us through the next 24 months in us, then bringing in. So you're going to hire a VP of sales. Don't hire a true CRO at 2 million. Hire a VP of sales. Somebody who's like, maybe got second line leadership experience has stage realities like stage relevant, has dealt with your type of deal.

00:36:16:14 - 00:36:47:17
Kyle Norton: Doesn't need to be only marketing. Like if you're martech, you have to hire from martech know. But if you're martech, you can hire somebody that's sold to like a similar profile or similar deal mechanics. Don't hire a deep tech salesperson at that point, or like somebody to sell, sold, or only to DevOps. But then success is great if like you're the VP sales and you get layered by a CRO and that person is like the one who helps this whole thing grow to the next couple of stages, I think that's the honesty that oftentimes is lacking.

00:36:47:17 - 00:37:14:08
Sahil Mansuri: And specific to SMB or there. Are there parts that that you would or a founder because again, if your deal sizes are 100 K, 200 K, 500 K, you're selling to Microsoft, you're selling to, you know, these big conglomerates. Yeah. The type of sales leader you need at a couple million RR, I think is markedly different than what you're dealing with where you know, the ASP.

00:37:14:08 - 00:37:18:11
Sahil Mansuri: I don't know exactly what owners ASP is, but I guess it's probably somewhere in 1020 K range.

00:37:18:11 - 00:37:19:14
Kyle Norton: Yeah. Exactly.

00:37:19:16 - 00:37:49:09
Sahil Mansuri: Yeah. So somewhere in that range like that's you know, for you to get to 20 million RR, in a couple years at a 20 Casp is if I can just do some quick math, a fuckload of deals and so like and and so like the capacity planning the tac, the quote, the velocity, the training, the culture, how much you can afford to pay a single rep, like all of those mechanics are just are specific to SMB.

00:37:49:11 - 00:37:59:06
Sahil Mansuri: Maybe you can get a little bit into that piece and then we can transition you. So touch on that from the leader perspective. And then we'll just transition right into the rep perspective of that and the team perspective of that.

00:37:59:06 - 00:38:22:20
Kyle Norton: So that is the jobs to be done. Part of the framework that founders need to get really considerate about and and really understanding what the job should be done of that individual are, because if you're selling a half $1 million solution, you only need 5 or 10 reps to get to like 10 or $20 million a year. So we're not talking about somebody that needs to operate with a ton of skill and systems and whatever.

00:38:22:22 - 00:38:51:21
Kyle Norton: My company, you know, we've got 60 reps at 30 million. Like there's just a different there's a very different skill set that you need to be able to to do that and grow at this velocity. And so for the SMB founders, I would say you absolutely need somebody who's like very systems oriented, very data, very data centric. They need to be they need to have, like a love for and a depth in coaching and leadership.

00:38:51:23 - 00:39:14:21
Kyle Norton: You know, enterprise reps don't need a lot of leadership, like pay them a bunch of money, make sure they can hit their quota, give them a good product, and like their their, going to happily chug on their, their are, very financially motivated. Oftentimes later in their career. They don't need all the like hoopla and and engagement strategies.

00:39:14:21 - 00:39:38:13
Kyle Norton: But you know, I'm hiring like 40 or 50 people this year in sales who are all going to be in the first couple of years of their career, like the I need to have a love for coaching and a love for enablement and, learning and development and so like, that's that's the key craft you're looking for out of, out of an SMB leader.

00:39:38:15 - 00:40:17:02
Kyle Norton: And then all the systems building, they have to know how to work a spreadsheet. They have to understand how to do a bunch of stuff in Salesforce. They have to be able to think in systems and really have that systems engineering mindset or else, like, maybe they can get you to like a couple million bucks, but then you will have brute force your way there and, grown on vibes and then everything starts falling apart because you don't have the systems and it takes so long to build the systems that then you see a bunch of these companies having like, this really bad stall out as, as the sales leader gets more than an arm's

00:40:17:02 - 00:40:44:00
Kyle Norton: length away from every rep, things start falling apart because that leader was making things happen on his own. He, he or she were pulling the strings themselves as opposed to building a system that can do it. And we you all in our business, we've been hired very early for rev ops leaders and enablement leaders, and we've been very systems oriented, which means like we've been able to plow in reps who come in, hit quota right away.

00:40:44:00 - 00:40:54:14
Kyle Norton: They set new records for first and second month, deal volume like every cohort. Because just the system gets better. And that's what you need for SMB leadership, I think.

00:40:54:15 - 00:41:16:15
Sahil Mansuri: Okay, let's talk about that because that's that's a really meaty topic. And it's one that, I think is often very misunderstood by founders, by a, by those who are at the 1 to 2 to $3 million range as they're trying to get to 20. You know, one of the things that, in the SMB and we're going to focus on SMB, okay.

00:41:16:17 - 00:41:53:16
Sahil Mansuri: One of the things that that we see all the time, I hear all the time, I'm sure you do, is a feeling of like, yeah, we just need like, a leader and some reps and we'll just make it happen. And, and this idea that, you know, things like rev ops, things like sales enablement, things like a tech stack, investment into building the foundation and the infrastructure are needed in advance of getting to the, the, you know, maybe when when they thought, you know, they're like, oh, we'll bring in someone to do rev ops that, you know, when we get to 15 or 20 million, we'll be in someone to do enablement when

00:41:53:16 - 00:42:11:15
Sahil Mansuri: we have like 20 reps, you know, and, and obviously that's going could be too late. So maybe talk me through your journey at owner in terms of again. So let's let's pick the thread up at one manager and two reps. Today you're at 60. Talk me through the hiring plan. When did you bring in the first rev ops person?

00:42:11:15 - 00:42:19:17
Sahil Mansuri: When did you bring in enablement? How did you think about the Ramp program? The onboarding program? I would love to understand how you built the system there. Yeah.

00:42:19:22 - 00:42:47:13
Kyle Norton: And so one sort of note of context, I think it's a chicken and egg problem because you you need to hire you need to have rev ops and enablement in order to grow at a certain scale. But you don't want to spend that money. And unless you're confident, you can get that scale because it's expensive, like you have a, you have a $200,000 a year, leadership level individual spread across six sales reps.

00:42:47:13 - 00:43:08:00
Kyle Norton: You're like, your cash just changed materially. But, if you are pretty confident that your six reps are going to be 18 reps within 12 to 18 months, then then you have to make that investment or else you're going to feel the pain later. And so I think founders need to be honest with themselves about like what's the trajectory we're really on here?

00:43:08:02 - 00:43:42:03
Kyle Norton: Like, do I have the the evidence that I'm actually going to grow at this trajectory and I should make these investments now or like, do I not quite have the product traction that I want. And churn is a bit of an issue. And I should take a more like moderate approach because you can find that capacity through contractors and so I even started that way, with owner, both, both my relapse and enablement leader started on contract because I just couldn't afford their their full time salaries spread across like a small quarter reps.

00:43:42:07 - 00:44:05:00
Kyle Norton: We were close to a fundraise. We had to be cash management, conscious. Like every startup. And so, I would say like pull the trigger on an early start, start with people on contract. That's a great place to go. You got to vet very carefully your contractors here because there's a lot of like, not great people in this, space.

00:44:05:02 - 00:44:31:07
Kyle Norton: A lot of out of work rev ops leaders that are like, I'm, I'm a consultant now, and they don't know what they're doing. But vet them out, and, as soon as you have the evidence of trajectory, then, like, bring that person in-house because you'll go, like, lots and lots faster. So I had those people working on stuff by like 3 million RR, probably.

00:44:31:09 - 00:44:37:22
Kyle Norton: And then they were full time in the business by 4 or 5. Wow. For sure.

00:44:38:00 - 00:44:39:00
Sahil Mansuri: That's early. Yeah.

00:44:39:01 - 00:44:42:08
Kyle Norton: It's funny. Does it feel I'm like, I wish I had done it earlier.

00:44:42:10 - 00:44:43:12
Sahil Mansuri: Really?

00:44:43:14 - 00:45:16:14
Kyle Norton: Yeah. Like because it's easy and it's easy with hindsight to to then see it's like okay, well we we went from, we went from 5 to 12 and nine or more more than that in like 12 months. And that cost looks insignificant when you're comparing it to like a 15 million or a $20 million run rate. But at the time, it just feels like it's real dollars.

00:45:16:16 - 00:45:41:12
Kyle Norton: But we have a good product and good market, so, like, we could make that bet. And we have scaled up those teams, like, significantly over the last six months. So there's like four full time headcount under Rev ops. There's three full time headcount under the enablement leader. And like we don't have enough capacity because I'm building this revenue leadership academy.

00:45:41:12 - 00:45:59:19
Kyle Norton: We're rebuilding like all of our product training onboarding got a facelift. We're like doing a bunch of positioning stuff there. So because, my mindset now is like, what is a $75 million for our company look like? And how fast can I be that level of execution? Because we're going to be there sort of in the blink of an eye.

00:45:59:21 - 00:46:02:03
Kyle Norton: It's it's crazy. All this time bleeds by.

00:46:02:05 - 00:46:20:04
Sahil Mansuri: So I love that. And that's and and I and I really appreciate the gut check that you need to do with your leadership team and with the company around. Are we sure that we are ready to make this investment now? Because I do think that there are companies where the product isn't there yet. The market isn't there yet.

00:46:20:04 - 00:46:42:09
Sahil Mansuri: You know, they don't have the proof point. And so that can lead to challenges. But I think that also comes back to our initial discussion around vetting the company more thoroughly to ensure that, like, you're not wasting your time at a place that's going to kind of putter along, you need to go into a place where you're, you're flexing in in order to really help, step function, change the revenue growth of the business.

00:46:42:11 - 00:46:43:11
Sahil Mansuri: I want to touch.

00:46:43:11 - 00:47:04:06
Kyle Norton: Just one more thing, like to make it a little more concrete, because I think maybe I was opaque. There. What you're looking for is evidence of go to market fit. And there's an article that Mark Roberts wrote called The Science of Scaling. And he talks about thinking about go to market fit the same way we think about product market fit and understanding.

00:47:04:06 - 00:47:27:06
Kyle Norton: Like, do we have evidence that this thing is repeatable and we could take in leads and reps, mix them together and then have revenue come out the other side. And once you start to see that repeatable reality and you can onboard three reps, two of them get to quarter on a on like a projected basis, and maybe one sort of gets there.

00:47:27:06 - 00:47:53:16
Kyle Norton: But it's always hard to hire. Then you then you can say it's like, okay, I have go to market fit. Now I'm graduating out of I'm graduating out of like prototyping and like pilot team building. And I'm now into, like, grow this thing. And so when I had 6 to 8 reps, we were, we were very much in this, like, we're prototyping.

00:47:53:16 - 00:48:11:05
Kyle Norton: I'm trying to get the economics to where I want it to be. Doesn't have to be exactly, you know, 4 to 1 LTV calc, but you need to see the the chart improving and you're like, okay, like I can reasonably project out another quarter and I'm going to be at that LTV calc number, I'm going to be at this productivity number.

00:48:11:07 - 00:48:31:22
Kyle Norton: And then, you know, hit the gas on those roles and then think about like, you know, six months ahead of look out six months and and just like project out where you think you'll be and what type of team you'll need to be then and start trying to hire those people now, because it takes a long time for them to hire and ramp and then actually do stuff that helps.

00:48:32:00 - 00:48:43:20
Kyle Norton: So I would say, like when you have that go to market fit based on Robertson's definition, that's a good point to that's a good place to say, like make these infrastructure investments pretty, pretty pretty, swiftly.

00:48:43:20 - 00:49:09:04
Sahil Mansuri: Totally makes sense. Let's talk about the rep profile a little bit on the SMB side, because you you touched on this. You said, you know, at enterprise, I'm, I'm looking for, you know, you can kind of get away with more senior people, less need for leadership, less need for this training, onboarding, ramp structure. Instead, what I'm going to do is I'm going to turn around and, and, you know, kind of get high, high paid, high profile reps.

00:49:09:04 - 00:49:27:12
Sahil Mansuri: And one rep can, a small number of reps can get it to a big revenue target because each deal is worth so much. Obviously, that's just not true in your world. I'm curious. I'm curious how you think about the profile of Rep, maybe the first 5 or 10 reps that you bring on, how that changes once the systems are built.

00:49:27:14 - 00:49:44:03
Sahil Mansuri: So maybe let's start before the infrastructure, before the systems. What are the reps you're looking for for SMB? And then and what are you like willing to pay out? And how do you think about quota a comp and how do you think about like all of that, versus once the systems are built, what does it look like at that point?

00:49:44:04 - 00:50:08:21
Kyle Norton: Yeah, as as Jason Lumpkin says, you know, when you're in that startup phase, you're really looking for pirates and romantics. You need to hire people that that really do care about the mission. I know it can seem sort of like a platitude and, and, just something that, like people say, but when you're only when you're only $2 million an hour are everything's broken.

00:50:08:21 - 00:50:41:03
Kyle Norton: Everything sucks. Like, you know, it's it's just like constant chaos and fires. And so you need people who love that, stage of the journey and have been there before. Like, you can't hire, you know, a public company enterprise rep to come be your rep at 2 million RR because they're used to having their decks built for them, and they've got the positioning statements all, tied up and a BTR to do this and an onboarding person to join the or a solutions engineer to join the call and basically like, show the product for them.

00:50:41:03 - 00:51:08:09
Kyle Norton: And none of that really exists. Early stages. So, so you need stage appropriateness. You're looking for pirates and romantics, and you're looking for people that are like Renaissance reps, basically people that that could sit down and like make a deck, you know, if they're like, oh, I actually think the positioning should look more like this and this, and this will sit down on a Thursday night and like, remake the the demo deck because they've got some sort of, inspiration from a previous meeting.

00:51:08:11 - 00:51:40:04
Kyle Norton: That's who you're looking for there. I opted so, so switching to SMB at owner, I opted to go hire. A more established rep. And hey, more, in the early days to ensure we just had a caliber of people that could come in and, like, get the job done. And so the the thing you have to be careful of is, like, those people still need to be adaptable.

00:51:40:06 - 00:51:54:00
Kyle Norton: You need to you need to hire for curiosity and coach ability, because sometimes you hire established people and they just want to do it their way and they can't adapt. But, I opted to find proven performers.

00:51:54:00 - 00:51:54:23
Sahil Mansuri: Pay.

00:51:55:01 - 00:52:23:21
Kyle Norton: At the top of the SMB market and, entice people to to take the risks just because, like the comp was really great and, you know, it helps to have some brand profile and like be a company that people know of. But that was a lot of the strategy. Now that we are very well established onboarding, enablement, the coaching and development, the management team is like very, very well-run.

00:52:23:23 - 00:52:41:22
Kyle Norton: Now I'm really trying to hire earlier career folks and, groom people from the start. And we are really trying to promote, promote from within as much as we possibly can. And that is going to have a very, like different cost profile.

00:52:42:00 - 00:53:04:10
Sahil Mansuri: What are some of the questions you ask? Well, let's go back to the Pirates and Romantics. What are some of the interview questions that you would ask or signals that you would look for outside of, like they've done this in the stage appropriateness and stuff, but like when you're talking to them, what are like 2 or 3 whatever questions that you would ask in order to assess if they are the this reticence rep that you are mentioning.

00:53:04:10 - 00:53:25:01
Kyle Norton: So I really just get into the how like, hey, you've had a bunch a bunch of times, you close like a $1.2 million last year, like walk me through how like how did you get to that number in people that are enterprising and creative are going to have a bunch to say there. Well, you know, we were doing this, but the data wasn't good in Salesforce.

00:53:25:01 - 00:53:50:10
Kyle Norton: So like when had a buddy pull a list, of like these types of companies and then I, and then I, built my, like, prospecting sequence, like, completely different. And they're just going to have a bunch of stuff that they did that was off script. And that's what I'm looking for. I'm looking for those creative ways that they got to their number.

00:53:50:12 - 00:54:13:10
Kyle Norton: And I really just want to understand, like how, like just get into the nitty gritty of, like, how did you get to your number? Tell me about your gnarliest deal. What was the hardest deal, the deal you're most proud of because you're going to you're going to understand a bunch of their creativity. And then I'm trying to get an understanding of like, was it them or was were they around it?

00:54:13:12 - 00:54:33:23
Kyle Norton: Because sometimes you've got an awesome sales manager who's solving all their problems and doing all this innovation, and they were sort of just executing. But I really want to understand what role did they play in this, in this whole thing. And the how is really important.

00:54:33:23 - 00:54:53:21
Sahil Mansuri: Well, what role, if any, to do you use demo in the interview for. This is a topic that I love getting into because it's so controversial. There's some people who are like, I basically every one of the things I hear founder and let me, let me set the stage for this question a little better. Founders will say this to me.

00:54:53:21 - 00:55:16:07
Sahil Mansuri: They will say salespeople are good at selling themselves. So ultimately, like where the rubber meets the road is, I want to see them demo the product and they make the sales rep demo the product of the, their own product. Right. So like if you're if you're interviewing to be a rep at owner and you currently work at Shopify, they'll have you demo a demo owner to to odor.

00:55:16:09 - 00:55:32:11
Sahil Mansuri: There's some who will say, well, you don't know enough about the product. And like it's hard with a surface level to be able to get depth. And so I'd rather have if you're if you're currently a Shopify rep applying for a job at owner, I'd rather have you demo Shopify for me so you can show me that that part.

00:55:32:16 - 00:55:41:15
Sahil Mansuri: And then there's a final group of people who will say demos aren't the right way to assess. So here's the third thing. I'm curious where you you stand on that.

00:55:41:16 - 00:56:03:23
Kyle Norton: Yeah, I definitely don't want them demoing their current product because there's such a massive asymmetry of information like, how do I know if they're doing that? Well, in especially if you're early stage or what? I'm what I'm trying to, what I'm trying to uncover is resourcefulness. Curiosity, learning aptitude because, you know, think of how fast startups change.

00:56:04:01 - 00:56:32:12
Kyle Norton: So if you can't visit our website and our YouTube page and listen to me drone on or on a bunch of podcasts and figure out how to position owner and do it on a demo, then you're not a fit. Earlier. Now I'm now we can be a little more flexible, especially because we're hiring earlier stage people. But at at a couple million dollars a year, they absolutely need to demo your product and they need to be able to figure that out because you're you're seeing their mental agility.

00:56:32:12 - 00:56:53:08
Kyle Norton: And that is like when you're talking about Renaissance reps, that is one of the most important things. Like do they have the creativity, agility, resourcefulness, scrappiness to be able to do that? Well? And sometimes people you know, like applicants will get a call with a rep and be like, hey, like, how do you position this? How do you position this?

00:56:53:08 - 00:57:14:07
Kyle Norton: And they're like demoing it, just like you teach your team because they sort of got the answer key. And some people are like, oh, like, I didn't really like that. That's not the point of the exercise. No, that is exactly the point of the exercise. Nick. What what could you do? How could you possibly go, get answers to these questions to do a great job at this.

00:57:14:07 - 00:57:35:18
Kyle Norton: And so for early stage companies, absolutely. Like you want them or want them pitching your company, you want to see, how they did it. And after they demo I asked them specifically, hey, so like so he'll like walk me through how you prepared today and then like, oh well I like did some research and then and I'm like, okay, what type of research and I'm like like I really want to know, like walk me through the details of how you got ready.

00:57:35:20 - 00:58:02:11
Kyle Norton: And then they start unpacking and they're like, I did this and I did this. And then I was like, I filled out a demo request with a fake restaurant, but nobody got back to me. So then I use a real restaurant. But then, like, you know, I'm trying to to understand how they problem solved, that I still love that in a more mature org, but it's not as much of a of a complete necessity.

00:58:02:13 - 00:58:08:14
Kyle Norton: And so I'm like definitely in favor of doing demos and, and unpacking their prep process for sure.

00:58:08:16 - 00:58:30:07
Sahil Mansuri: I love that. Can we talk a little bit about the team side of it? Like that's on the individual rep, on the team side of it? You know, one of the things that that's, in vogue to discuss, these days on like did is remote versus in-person teams. And I think there's this there's a feeling. So maybe start with is is owner, in-person remote.

00:58:30:07 - 00:58:32:11
Sahil Mansuri: How are you how are you guys structured?

00:58:32:13 - 00:58:53:00
Kyle Norton: So we have been remote since the jump. Our entire sales team is remote. But I just announced on Monday that we've opened up an office here in Toronto, a sales hub that opens up on January 27th. And we're now hiring all new builders and stars locally that will have a five day a week, in office expectation.

00:58:53:02 - 00:58:55:11
Sahil Mansuri: Why did you decide to do that?

00:58:55:13 - 00:59:15:07
Kyle Norton: So I spent a lot of time with a lot of sales leaders trying to figure out this question, because earlier last year I would ask this question and people like, well, it's got to be an office. Office is the best. But then I would like unpack it. And again, people are just reasoning by analogy and they're like, oh yeah, it's better because blah blah blah.

00:59:15:07 - 00:59:33:07
Kyle Norton: I'm like, well, what data? What like what? Like what what data do you have to support that decision? And nobody had anything. They weren't doing AB tests. They didn't have a good comparison. And largely I would talk to companies and they would say they just brought people back into office. And then I would ask them about their remote onboarding enablement.

00:59:33:07 - 01:00:03:16
Kyle Norton: And it's terrible. It's like, yeah, well, no wonder remote wasn't good for you guys because you were like brutal at it. And we do, I would say like a really good job at remote onboarding and enablement. But then I started to finally get to some companies that had done more proper AB tests and had done side by side experiments, and the data started to be like, like pretty unequivocal that reps ramped faster and, and I've got like pages and notes, but some people had a 20% faster ramp.

01:00:03:16 - 01:00:34:18
Kyle Norton: Some people had like people ramping, and half of the time productivity was better by like 30 to 60%. You shared some data on, on our podcast about, in-office versus remote, attainment for SMB reps. So I went deep. I was reading like academic research and, and and really trying to make an informed decision. And I think so the rationale is people will ramp faster if they're around a bunch of their peers, including their managers.

01:00:34:19 - 01:00:55:05
Kyle Norton: Productivity will be better because you're not just like sitting alone in your apartment trying to, like, muster up the courage and motivation to make calls. I think, like it's just way easier to do that when your office is a vibe and people are like being in L calls and having a good time, and, you know, you can, get help at arm's reach.

01:00:55:06 - 01:01:15:18
Kyle Norton: And I think retention will be better because, you know, young people especially like moving to a new big city. They don't know a ton of folks like their the sense of community is really important. And all of the engagement research shows that how important that community is. And obviously it's much, much harder to build community in a remote environment.

01:01:15:20 - 01:01:29:14
Kyle Norton: So we're moving everybody back in. We're not we're not, this is not return to office. Our current remote team can stay remote as long as they want their field filled. They're free to come into the office. But moving forward, everybody's going to get hired on in the office.

01:01:29:16 - 01:01:34:07
Sahil Mansuri: When you say everybody, just to be clear, that's STRs and BD. Or is that also EES.

01:01:34:09 - 01:02:05:12
Kyle Norton: SDR is and BD and inbound EES, inbound inbound EES will almost exclusively be promoted from within from that BTR group. But then I don't have the, the gates established right now. I want to learn a little bit more, but at some point, people will graduate from five days in office to hybrid to fully remote. Your data was really informative here, and I started asking this question more frequently.

01:02:05:13 - 01:02:39:13
Kyle Norton: And so at some point, a rep is tenured enough and understands your business well enough that they no longer, they no longer need or are, like, benefited by the office experience. Like they know how to manage themselves and, and run their calls and the, the work life integration of being remote becomes more important, as their, you know, in their late 20s and maybe have a partner and or thinking about leaving the city.

01:02:39:13 - 01:02:53:21
Kyle Norton: Like I think the, the attraction and retention advantage at some point outweighs the learning advantage. I don't know at what point that is. The data is going to tell me that, but it's, we will graduate people out to hybrid and remote eventually.

01:02:54:00 - 01:03:18:23
Sahil Mansuri: I didn't expect that answer. And I'm and I'm and I'm super interested in your in your thinking around it because from the outside Ed you said you joined owner in June of of 22. We're now in January of 25. And so we are you know what is that 2430 months in and in 30 months you've increased IRR by roughly 30 million.

01:03:19:01 - 01:03:50:10
Sahil Mansuri: So you know, you would think if it ain't broke, why are you trying to change something? Given the investment that you've made in enablement, in, you know, onboarding these people, it doesn't seem like there's a problem. Maybe there is, and I'm missing it. But I'm curious. You know, it's one thing to say, hey, other companies have found the data to suggest that, having a in person team leads to higher productivity.

01:03:50:12 - 01:03:56:12
Sahil Mansuri: But has productivity of your junior team been a problem for, you know, historically.

01:03:56:12 - 01:04:00:15
Kyle Norton: So it's getting better every month? In fact, every quarter productivity then why.

01:04:00:15 - 01:04:02:08
Sahil Mansuri: So then if it ain't broke, why fix it?

01:04:02:14 - 01:04:30:07
Kyle Norton: Because that is where companies, this is where companies get into problems. Is, is, they think that doing the same thing into perpetuity will get them to their eventual goal. But, so we probably hired, like, maybe 20 bidders this year or 15 to 20 bidders, and we likely need to hire 35 to 45 next year.

01:04:30:12 - 01:04:31:06
Sahil Mansuri: Yeah.

01:04:31:08 - 01:05:03:18
Kyle Norton: Those are just bigger numbers with, more volatility and variability. And so I think taking risk off the table is important by like having everybody co-located, especially as we really try to, to to have everybody manufactured from ground up, like getting tons of stars in graduating them through BTR senior, BTR 80 and and so forth. I think like complacency is the biggest is the number one enemy of success.

01:05:03:18 - 01:05:25:07
Kyle Norton: And I said this to my team today like, hey, by the way, you know, we had a super successful 2024. We had an awesome all hands on Monday where we like went through all the cool achievements and the data is wild. You're like, wow, we did that. That's awesome. Everybody patting themselves on the back and the message I shared with my team is like, look like every great company has a brush with death.

01:05:25:09 - 01:05:43:06
Kyle Norton: Tesla, SpaceX, Apple, Google, Facebook, like they all have. You know, they all have famous examples of of almost running themselves off the road. Facebook with mobile, Tesla with production. If you've read the Musk bio and in Facebook with.

01:05:43:09 - 01:05:50:14
Sahil Mansuri: Facebook, with changing to meta and investing everything in metaverse. Yeah, yeah. Anyway. Yes. Go on.

01:05:50:16 - 01:06:08:09
Kyle Norton: So like for us to think we're not going to have a brush with death is is naive. And things have been pretty awesome for the last like 2 or 3 years. And so I said to them I was like, look, and we're going to, we're going to have a probably pretty great next couple of quarters because everything's lined up nicely.

01:06:08:14 - 01:06:34:11
Kyle Norton: At some point, something will go off the rails. It'll be like some competitive reaction will be some black swan event. Something weird will happen to this business that's going to make us make it. Things way harder than it is today. And we need to be we need to be ready for that. And of the mentality that like we are expecting something bad, something to go wrong so that we're mentally prepared, that when it does go wrong, it's like, okay, cool.

01:06:34:11 - 01:06:46:03
Kyle Norton: Like I expected this, did we expect things to be perfect forever? No, that would be silly. So like go in with the preparation that things will go wrong. And when it does happen, then it's it's much easier to react to.

01:06:46:05 - 01:07:20:06
Sahil Mansuri: And so and so you feel like this is an area where you're de-risking something that you think it's working well today. But if I was to play the tape forward, I think that there's a possibility that we will see, volatility and reduction in performance on our like most junior employees, on the sales team and potentially and so in order to potentially de-risk that, we're going to we're going to co-locate and trade and invest in this group, in Toronto.

01:07:20:08 - 01:07:28:06
Sahil Mansuri: And and in doing so, we will set ourselves up potentially to avoid one of the pitfalls that I could see coming down the road is that is that kind of the assessment?

01:07:28:07 - 01:07:55:17
Kyle Norton: Yeah. Yeah. And and every year the bar goes up. You know, I have it I have the expectation that I can drive down cash by a materially amount. I have a I have the expectation that I can grow the company faster. And, you know, this is one of those big levers that, on a productivity ramp, output cost basis can, can really have an impact.

01:07:55:17 - 01:08:22:03
Kyle Norton: And so I've validated a lot of my assumptions pretty heavily with the market. You know, one of the companies I talked to, saw over a 60% difference in activity volume between hundreds of orders that, call it 100 bidders remotely versus their two in office experiments that have roughly like 30 to 40 bidders in it, a 60% activity difference.

01:08:22:03 - 01:08:48:14
Kyle Norton: And this is a company that's extremely well-run and has a great remote like, great understanding of how to do remote like best in class. And and yet those teams are just like smoking everybody. And so I, I think like you have to make bold bets even when things are going well or else at some point growth slows and and I intend on growth being faster in 2025 than it was in 2024.

01:08:48:16 - 01:09:14:13
Sahil Mansuri: That's such a amazing owner mentality as a as an executive, you know, to say, to say I demand more out of my team. Despite having overshot and overachieved last year, just raises my own bar of expectation and that I'm going to be a student of trying to figure out what are all of the, you say lever, I say lever, but, you know, there we are.

01:09:14:18 - 01:09:37:14
Sahil Mansuri: All of the all of the the levers, that you can pull in order to accelerate growth. I mean, I just I just feel like that's that is something that a lot of sales leaders are doing, you know, like, I'm in conversations that I have with a lot of sales leaders. There does seem to be this desire to say, hey, last year we grew revenue by 400%, but that was on a small base.

01:09:37:14 - 01:10:03:20
Sahil Mansuri: You know, next year, of course, it's going to slow down. And so I want to set quote unquote realistic targets. I want to sandbag a little bit on the business so that I can set myself up to be successful as opposed to what you're describing, which I think is the dream for every founder, which is to find somebody who says, last year was great, but I know we can do better, and I'm going to keep finding ways to do better because that's what my job entails.

01:10:03:23 - 01:10:13:09
Sahil Mansuri: You know, it's a really it speaks volumes to your mentality as a leader. And I think it's super, super cool. And I'm and I'm excited to see how it works out.

01:10:13:11 - 01:10:35:07
Kyle Norton: Yeah, I so the, the number I got from finance, I took that up a material amount. I was like, but this is my number. We have a joke internally. There's always a Kyle number. Like there's a every month. There's like the number from finance. And then there's like always a Kyle number, which is like 20% above it.

01:10:35:07 - 01:11:14:03
Kyle Norton: And it's it's not the that's not the roll up. That's not like, you know, any funny business. It's just like, yeah, okay, this is the number we've said this is going to get us to our target. But like let's go, let's go 15% above that. Like, I think we can do it if we do these things. And that drumbeat and that intensity from the top, I think as a crucial impact on how people operate because of the moment, like the moment you take your foot off the gas just a little bit, the moment you feel happy about where you are and complacent, and you want to give yourself a pat on the back, that's the

01:11:14:03 - 01:11:34:00
Kyle Norton: moment things start to like just crack at the seams ever so slightly. And that compounds over the course of like months and quarters and all of a sudden, like, growth has slowed and now you're like no longer that exciting to invest in. And then your round as in as good nick grounds, not as good. Then you don't attract the super top talent anymore.

01:11:34:01 - 01:12:00:00
Kyle Norton: Like success is so fickle in our business. And so like my message to revenue leaders is like, no matter the number you get, no matter the number that you get from your your finance team or the board, like make your own determination of what's possible and don't go shoot for the number. Go shoot for what? What's possible. If I could really, like, run the table.

01:12:00:00 - 01:12:16:14
Kyle Norton: Like then where? Where do we end up? Because you know that that's a company I want to run. That's the company I want to be a part of. I want to be a part of, like a insane success story. And, you know, we don't do this, you know, to this job to like, check a box you need. You needed something.

01:12:16:14 - 01:12:37:16
Sahil Mansuri: Different. Well, I mean, I honestly could do I feel like I'm Lex Friedman today and not in the quality of my podcasting, but in the length of podcasts that I could go for solely because I. I feel like I've just began to scratch the surface with you. And I have so many questions I want to ask you about product positioning.

01:12:37:16 - 01:12:58:20
Sahil Mansuri: I want to ask you about. Yeah, in differentiation. I want to talk to you all about, you know, the tech stack that you've built, in order to support and enable and get there. But I also want to be respectful of your time, and not keep you forever. Let's do another one, ASAP. I want to do a part two with you this, this quarter.

01:12:59:01 - 01:13:28:06
Sahil Mansuri: And this time I want to get all into, you know, the product positioning, differentiation and stuff because it does change, quite dramatically. But before I go, I want to leave you with a quick, hot fire. Round robin. And I've got two questions that I want here over one. The first question is, what is the best advice that someone gave you early in your sales career that you think that if today people were to give this advice, it might get canceled by by the, by the mob?

01:13:28:08 - 01:13:33:13
Sahil Mansuri: What's something that's considered controversial today that maybe you really took to heart early in your career.

01:13:33:15 - 01:13:57:19
Kyle Norton: But the vibe is shifted, so I like I would have previously said that like, you can expect, a successful career without tons and tons of hard work. Like, it feels like the last couple of years, hard work became taboo. And then, like, you weren't allowed to ask for hard work as a leader because you were triggering your employees or whatever crap language people use.

01:13:57:21 - 01:14:17:07
Kyle Norton: But I absolutely believe, like, you can't expect an extraordinary career with an extraordinary effort, and people want one without the other, and it's just not possible unless you are so much more talented. You are 1 in 1,000,000 in terms of like raw ability. Okay, maybe you don't have to work that hard to be super successful. That's not me.

01:14:17:09 - 01:14:38:12
Kyle Norton: And I that's not 99.99% of people. So just like hard work is, is essential if you want to get anywhere, and hard work is not 45 hours a week, hard work is like 50, 60, 70 hours a week. Like if you really want to have a remarkable career, like that's what we're talking about, like that real, like real hard work.

01:14:38:13 - 01:15:01:07
Sahil Mansuri: My wife got canceled by posting that the best thing she ever did was to work weekends early in her career, and the tweet went super viral. And like, literally like thousands of people are like, how dare you suggest that people spend their weekends working for the man and like, whatever. Like it was just insane to me because I never had a weekend off for the first five years of, like, Chris, Doug barely still take a weekend off.

01:15:01:07 - 01:15:08:22
Sahil Mansuri: Like the idea of not working for, you know, 48, 60 consecutive hours just doesn't make any sense to me. So it's it's crazy.

01:15:08:22 - 01:15:25:16
Kyle Norton: You can you can do the 40 hour workweek thing. That's cool. Like the no judgment, but just don't expect like, really remarkable career outcomes. Like because somebody, somebody with your equal talent is going to do 60 hours a week. That's right. And they're going to get the job. They're going to get the thing.

01:15:25:19 - 01:15:43:12
Sahil Mansuri: And then the last question I'll let you go is, what is one place that you have used your sales superpower outside of work where it has benefited you? You got a quick little story of how you use sales in order to help get you out of the situation or help get into you, you into a situation that you think is kind of fun to share.

01:15:43:14 - 01:16:06:01
Kyle Norton: Oh man. Everywhere. My wife hates it when I do this. She finds because she finds sales so uncomfortable. But like, I just love negotiating. So we renovated our house a couple of years ago and bought all new appliances for the kitchen, and I had like four different appliance distributors on the go. And I was like, hey, this company said this, can you get it for me for that?

01:16:06:05 - 01:16:20:07
Kyle Norton: Like, oh, I don't know. Or I will like, you know, semi semi that the, the best you could do and I would screenshot the best that they could do and send it to the next person. My wife is like you're just having a time aren't you. You're a complete sicko. I'm like yeah for sure. Same thing when we bought a car.

01:16:20:09 - 01:16:47:19
Kyle Norton: So I probably saved 25% on the appliances and it's like, you know, I've put thousands and thousands of dollars to buy all new appliances. I probably save 25%. I got crazy deal on my car because I was doing the same thing. I called every dealership in Ontario and I was like pitting them all against one another and and, I love to negotiate because, like, you know, when you're in a position like ours, you got to be a good negotiator.

01:16:47:19 - 01:16:55:22
Kyle Norton: You have to end like, I know all the tricks. I've read all the books, and so I know how to play. Play the other side. That's probably the biggest place.

01:16:56:00 - 01:17:00:03
Sahil Mansuri: You, sir. Or what we would call a real sale. Savage. That's amazing.

01:17:00:05 - 01:17:01:22
Kyle Norton: Yeah, exactly.

01:17:02:00 - 01:17:10:07
Sahil Mansuri: All right, Kyle, I'll let you go. Brother. Thank you so much for being on the board, sharing your wisdom and insights. And, we're going to do round two this quarter. I'm going to hold you to that.

01:17:10:09 - 01:17:11:10
Kyle Norton: All right, let's do it, man.

01:17:11:11 - 01:17:12:18
Sahil Mansuri: Take it easy.