Scaling SMB to $30M, Investing in RevOps Early, and Stage-appropriate Sales Hiring with Kyle Norton

You have to make bold bets even when things are going well or else at some point growth slows. And I intend on growth being faster in 2025 than it was in 2024. 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's possible. If I could really run the table, then where do we end up?

Foreign. Hi everyone. Welcome to the Bravado podcast. Our goal here with the Bravado podcast is to find the CROs, VPs of sales, 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. And joining me today is the legendary CRO of owner.com, kyle Norton, previously led sales at Shopify. Kyle, welcome to the Bravado pod, man. So excited to have you.

Yeah, thanks for having me. I'm excited for this one.

Yeah, 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. I'd be super interested to hear.

Yeah, so when I was 17, I think like many sort of the early days of the U.S. uFC just was in enthralled with that as a sport. And especially, you know, watching hoist Gracie, who was a Brazilian jiu jitsu guy, 160 pounds, tapping out like massive behemoth 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. And 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 the only thing I cared about for the better part of eight years. 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 a obsession of mine. And I give it, I give martial arts a lot of credit for who I became as a business Leader just because you learn like in 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.

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 SaaS sales?

Like most people, I just fell into it out of college. There was a, 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. 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 meritocracy of sales spoke to me. So I just, you know, like randomly stumbled into it and then I was with a was there for four or five years boiler room type environment, you know, like cold calling 150, $200 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 I cold called my way into my first tech job actually. Cold called Mark Bergen who was the EVP sales at Vision Critical and then ran revenue at Shopify later. 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. And through the cold call and a conversation then broke my way into tech where I ran a global BDR team for a little while there.

You want to talk a little bit about. You're. One of the things you and I have talked about is, you know, a lot of times as a salesperson 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% as hard, you can still get much more in terms of results and quota and whatnot. And then the magic intersection of great product meets great work ethic and ability is where the really amazing stuff happens. We'd 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 and the right product versus just getting a role in.

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. And so you really had to learn how to sell around that and spin and you know, we probably took it too far to be honest. Like where you could sell anything, you could say anything to get a deal done. 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. And so I think in 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 awesome. So while I didn't have a good product, I had a great learning environment and I had great leaders to learn from. 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 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 in a poor performing product. I say 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. It's like my first VP of sales job. And then you look at the founders and you look at the product and you look at the, the market and investors, you're like, this is doa. Yeah, you got your first VP of sales, 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, you're really just a glorified manager. You're. You're managing four 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 director 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.

There's so much goodness to that. But the one, the one thing I want to call out is upfront, 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 to, you know, Google and then now join a series A company. 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 an exaggerated grind. We had 1,000 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. I'm not joking. Like, this company crazy. This company was basically selling the shittiest product on the planet. And, and, and, and now they've made a lot more investments. The company's much better. But like back in 2008, 2009, like, this company was a disaster. And it was the same thing where you, I mean, you couldn't rely on in. There was zero inbound. There was the most common response you got when you talked 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. We had insane product market fit.

So fun.

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 at Meltwater. That I knew how to make something from nothing, 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 getting stopped. 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 them.

Yeah. 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. 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, they couldn't possibly be good in a startup. 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 core foundation of, 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. Hey, how you doing? People were like, excited to hear from us and it was like the weirdest thing. I like it, like, couldn't under like it just like Baffled me as somebody who had never sold a great product before in till shop. And what you're looking for is, is the DNA of, of. Do they understand the science of persuasion? Do they have grit and resilience even though 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, 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 like, you know, I was a leader at Shopify, a big company on paper, but I had my hands in everything. Like we were rerenting our global sales positioning, so I'm like, hey, let me be the revenue sponsor on that. And the. 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. There was other people in my similar seat that like weren't going to go take on those like gnarly, complex things. And so 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, 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.

We're on the topic pretty deeply now of what should a founder look for when they're looking to bring an early stage leader on. 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, et cetera, and roughly what stage you're at now obviously don't need specifics, but just roughly, you know, about revenue, about sales, team size, et cetera, 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 Norton. So maybe just give us some context first and then we'll, and then we'll dig in.

I joined owner in June 2022. They were 2 and change million ARR 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 actually crushing now. We're right around 30 million ARR. The sales team as of like Monday is going to be about 60 people and I, I have the onboarding function as well. Rev ops, enablement partnerships in BD and whatever else is sort of like related. Yeah, so that's the journey.

Okay, so let's go back to 1 like frontline manager, 2 to 4 reps, 2 million in ARR and change. So that's a pretty unproven product and a pretty early. As far as early goes, that's pretty early. So what?

It's so early that I said I would never go back to a company this early before I took this job.

Okay, I want to dig into that in just a second. But before we do that, let me ask the product 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?

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. And there's lots of people who stay for a long time, but the caliber of the co founders determines basically everything after that. 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. And then product quality. And so like at that stage you're grading on a curve. But is this a good, good product and is it getting better fast? And those three Things were very much there in, in owner. I, I, so I'm a part of g, I'm an LP in GTM fund. They invested in owner. I was a part of the process to get GTM fund into that deal. Basically like Scott, who you and I both know well, Scott Barker was like, hey you, we got this deal. It's shithot. We, we like absolutely want into it. So I need you to get 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. 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. Convince this founder that taking our money is great because he'll get access to people like you. So I hopped on 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? So do they have like a will in a like an unnatural will and drive and resilience. Resilience and can. And do you 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? And I remember on my first or second call with Adam, I rec. I recommended this book. I'm like, oh yeah, 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 texted 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. 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 opportunity should have the right to win in this market? And Adam basically started this business for his mom and was high, 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. 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, they're C suite and they just sort of drive the thing into the wall. 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 like 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. Like I'm a, I'm a massive fan. Uh, but I just could not, not take this opportunity cause I thought I might regret it for basically the rest of my career. Just watching them rip on LinkedIn and, and knowing I could have been a part of the journey.

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 criteria. Uh, 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's, that's great but like at that stage most products aren't that great. And so like how do you think about that and your idea around founder market fit I really enjoy and 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 for sure.

You know when I was considering Glassdoor I had two other offers and both of the offers were. It's funny, you're somebody. 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 at two shitty companies. I didn't know they were shitty because I was 24 years old, which I didn't know anything. But I had the opportunity to be the number one at two, you know, like less well established companies or to be the number two at Glassdoor. And I was leaning towards. I actually initially said no to Glassdoor's offer because I wanted the VP of Sales title. I wanted the, you know, three fourths, the three Quarter point equity that came with it. Glassdoor 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. He basically, he and I were email. So 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 of sales title or whatnot. But he basically broke down for me how I should be thinking about evaluating a startup. And for context, Bob was, you know, 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, look, benchmark backed Glassdoor like Benchmark does eight deals a year. They are one of the like most premier, yeah VCs. And Rich Barton is on our board. He's like one of the top 10 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 three fourths of a point of nothing is still nothing, you know, but here I think they had offered me, if I remember correctly, it was like.02% of the company is what it was. So I was basically getting like 1:34 or whatever of the offer that I was getting from. These are 137.5 of the offer that I was getting from this other. He was like, is, is. Is going to, it could be worth a lot more. 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 salesperson that he had ever interviewed who negotiated purely on equity. 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 it would matter. And I Ended up actually taking a lower base, lower kind of smaller commission plan, obviously uncapped, 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 stuff and then, and then have the opportunity to found, to found 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 as, as it has for you, I'm sure. And it's just really, really meaningful.

Absolutely. I think like the caliber of investors is important and like Jason Lemkin is on the board here who I followed since like the earliest days of my tech sales career and have a tremendous amount of 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 similar to like, don't just, don't just look at the resume. Like, try to get to what's underneath. 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 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 $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. 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 nrr 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? What are your top close, last 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 CEO 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. 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, 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? They write a handful a year. You write one of you make one of these decisions every like two to four to 10 years. So, so arguably your diligence, your company diligence should be quadruple what an, what a venture capital investor does, what, who, what revenue leaders are doing, that level of diligence. Like almost none.

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, there's, there's no, there's no second there's, there's no take backs on that.

You can only make a couple wrong choices before people start questioning your resume. If you have, if you have two 9 month stints to 9 month VP of 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, I need people with business acumen or they're bad at their job. So you have to be really choiceful about it.

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 a head of sales, a VP of sales in order to take this thing from 2 to 20. What are the heuristics what are the criteria? What are the things that you would want to spend some, some time evaluating, understanding both on a resume for initial screening, in conversations that you think leads to the best possible chance of success?

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 this is the framework that I give them. So they need to be really considerate about like what are the specific jobs to be done of this, this role? And you can't, 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. They need to be like the super duper rep and they're going to play that role for quite a long time. Like at 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. 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 Hu talks a lot about is just like the importance of scorecarding, the importance of sitting down and thinking very considerately, like what are the jobs to be done? What are the competencies I need to screen for? And then what are the experiences, 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, 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 incongruency like it, no matter what you do, it won't work. If you were a top down authoritarian and this person is like a bottoms up and like empowerment, engagement leader, like it's not going to be, it's not going to be a good fit. 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 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. Well, 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 procurement sign off on stuff like that. 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 are you really carefully assessing that, that it's their in the candidate then like the real skills and the skills need to be applicable to your market. 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, 10 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. I can pull people, people down.

Yeah. But if you're, but if you're looking for someone, if you're at like 2 or 1 or 3 or something like.

That, 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 sales leaders. But I think we should be honest about both sides of this equation. Most of the time. 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. 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 keep Being your VP of 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. 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 VP 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. And I think, you know, again, this comes back to sort of like vanity and ego. Many and Lemkin talked about this on my podcast with him and he's talks about this a bunch externally. Like how you react to getting layered is, is like very, is very telling. But a founder should just be honest. It's like hey look, success here looks. Success here looks like you getting us through the next 24 months and 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 relevant, is like stage relevant, has dealt with your type of deal. Doesn't need to be only marketing. Like if you're Martech, you have to hire from Martech. No, but if you're Martech, you can hire somebody that's sold to like a similar profile with similar deal mechanics. Don't hire a deep tech salesperson at that point or like somebody who sells sold only to DevOps. But then success is great if like you're the VP of 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.

And specific to SMB, are there parts that you would orient a founder? Because again if your deal sizes are 100k, 200k, 500k, you're selling to Microsoft, you're selling to these big conglomerates. The type of sales leader you need at a couple million ARR, I think is markedly different than what you're dealing with. Where you know the ASP. I don't know exactly what owners ASP is, but I guess it's probably somewhere in 10, 20K range.

Yeah, exactly.

Yeah. So somewhere in that range like that's a, you know, for you to get to 20 million ARR in a couple years at a 20k ASP is if I can just do some quick math, a fuckload of deals. And so like, and, and so like the capacity planning, the cac, the quota, 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. Maybe you can get a little bit into that piece and then we can transition 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.

So that is the jobs to be done part of the framework that founders need to get really considerate about and really understanding what the jobs to be done of that individual are. Because if you're selling a half a million dollar solution, you only need five or 10 reps to get to like 10 or $20 million. ARR. So we're not talking about somebody that needs to operate with a ton of scale and systems and whatever. 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 S and B 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 a like a love for and a depth in coaching and leadership. 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 gonna happily chug on. They're, they are very financially motivated oftentimes later in their career. They don't need all the like hoopla and, and engagement strategies. 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 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 a, out of an SMB leader. 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 couple million bucks but then you will have brute forced 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 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 system that can do it. And we, you know, 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. 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.

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, 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 S and P. And we're going to focus on SMB. Okay. One of the things 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 at, you know, when we get to 15 or 20 million, when we in someone to do enablement, when we have like 20 reps, you know, and obviously that's going to 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 revops person? When did you bring in enablement? How did you think about the ramp program, the onboarding program? Like would love to understand how you built the system there.

Yeah. 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 revops 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. You're like that your CAC just changed materially. But if you are pretty confident that your 6 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? 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, I even started that way with owner. Both, both my revops and enablement leaders started on contract because I just couldn't afford their, their full time salaries spread across like a small corridor reps. 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 it. Early start, start with people on contract. That's a great place to go. You gotta vet very carefully your contractors here because there's a lot of like not great people in this space. A lot of out of work rev ops leaders that are like I'm a, 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 ARR probably and then they were full time in the business by four or five.

Wow.

For sure.

That's early.

Yeah. It's funny, it doesn't feel, I'm like I wish I had done it earlier.

Really?

Yeah, like because it's easy in high it's easy with hindsight to, to then see. It's like okay, well we, we went from, we went from five to 12 in 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. But we have a Good product and good market. So like we, 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 RevOps, 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. We're rebuilding like all of our product training, onboarding got a facelift. We're like doing a bunch of positioning stuff. There's so. Because my mindset now is like, what is a $75 million error 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. It's, it's crazy how this time bleeds by.

So I love that and that's, 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. 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.

I want to touch 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 Marco Bears 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. 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 repeatability and you can onboard three reps, two of them get to quota on a, on like a projected basis and maybe one sort of gets there, 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, I'm now into like grow this thing. And so when I had six to eight reps we were, we were very much in this like we're prototyping. 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 CAC 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 CAC number. I'm going to be at this productivity number 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. So I would say like when you have that go to market fit based on Robert's definition, that's a good point to, that's a good place to say like make these infrastructure investments pretty, pretty, pretty swiftly.

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 and one rep can, a small number of reps can get to a big revenue target because each deal is worth so much. Obviously that's just not true in, in your world. I'm curious, I'm curious how you think about the profile of rep, maybe the first five or ten reps that you bring on, how that changes once the systems are built. 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 to 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?

Yeah, as, as Jason Lemkin 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 in error, everything's broken, 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. You can't hire, you know, a public company enterprise rep to come be your rep at 2 million ARR. Because they're used to having their decks built for them and they've got the positioning statements all tied up and a BDR 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 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. That's who you're looking for there. I opted so, so switching to SMB at owner, I opted to go higher, a more established rep and pay 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, and so the, the thing you have to be careful of is like those people still need to be adaptable. You need to, you need to hire for curiosity and coachability 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, pay at the top of the SMB market and entice people 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 now. I'm really trying to hire earlier career folks and groom people from the start and we are really trying to promote from within as much as we possibly can and that is going to have a very like different cost profile.

What are some of the questions you would ask? 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 two, three, whatever questions that you would ask in order to assess if they are the. This renaissance rep that you are mentioning?

So I really just get into the how, like, hey, you've hit quota bunch of times. You've closed like a $1.2 million last year. Like, walk me through how, like, how did you get to that number? And 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. So I like went and 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. 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? 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.

What role, if any, do you, 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. 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 owner to owner. 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. 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 set you, you stand on that.

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? And especially if you're early stage, 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. So if you can't visit our website and our YouTube page and listen to me drone on 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 a couple million dollars ARR, 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. 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? And they're like demoing it just like you, 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. Like, what, what could you do? How could you possibly go get answers to these questions to do a great job at this? And so for early stage companies, absolutely. Like, you want them, want them pitching your company, you want to see how they did it. And after they demo, I asked them specifically, hey, so like Sahil, like, walk me through how you prepared today. And they're like, oh, well, I like, did some research and da, da, da. I'm like, okay, what type of research? And I'm like, I really want to know, like walk me through the details of how you got ready. And then they start unpacking and they're like, I did this and I did this. And then I was like, I, I filled out a demo request with a fake restaurant but nobody got back to me. So then I used a real restaurant. But then like, you know, I, I'm, 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. And so I'm like definitely in favor of doing demos and unpacking their prep process. For sure.

I love that. Can we talk a little bit about the team side of it that's on the individual rep on the team side of it. One of the things that's un vogue to discuss these days on LinkedIn is remote versus in person teams. And I think there's a feeling. So maybe start with is owner in person remote? How are you? How are you guys structured?

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 BDRs and SDRs locally that will have a five day a week in office expectation.

Why did you decide to do that?

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, oh, it's gotta 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. 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 a B 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. 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, I'm like, pretty Unequivocal that reps ramped faster. And I've got like pages of notes, but some people had a 20% faster ramp. Some people had like people ramping in 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 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. 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 banging out calls and having a good time and, and you know, you can get help at arm's reach. 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 com. The sense of community is really important and all of the engagement research shows that how important community is and it obviously it's much, much harder to build community in a remote environment. So we're moving everybody back in. We're not. We're not. This is not returned to office. Our current remote team can stay remote as long as they want. They're free to come into the office. But moving forward, everybody's going to get hired in, in the office.

When you say everybody, just to be clear, that's SDRs and BDRs or is.

That also AES, SDRs and BDRs and inbound AES. Inbound. Inbound AES will almost exclusively be promoted from within, from that BDR group. But then I don't have 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. 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 they're, you know, in their late 20s and maybe have a partner and are thinking about leaving the city. 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 we will graduate people out to hybrid and remote eventually.

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 in you said you joined owner in June of, of 22. We're now in January of 25. So we are, you know, what is that, 20 for 30 months in and in 30 months you've increased ARR by roughly 30 million. 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 how 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. But has productivity of your junior team been a problem for you historically?

So it's getting better every month, in fact every quarter. Productivity on a.

So then why, so then if it ain't broke, why fix it?

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 bdrs this year. 15 to 20 bdrs.

Yeah.

And we likely need to hire 35 to 45 next year. Yeah, 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 have everybody manufactured from ground up like getting tons of SDRs in, graduating them through BDR Senior, BDR AE and so forth. I think like complacency is the biggest, is the number one enemy of success. 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. 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.

And Facebook with Facebook with changing to Meta and investing everything in Metaverse. Yeah, anyway. Yes, go on.

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 two or three 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. At some point, something will go off the rails. It'll be like some competitive reaction. It'll 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, there's something to go wrong so that we're mentally prepared that when it does go wrong, it's like, okay, cool, 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.

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, potentially. And so in order to.