Scaling B2B from inside the CRO seat — Kyle Norton (Owner.com, ex-Shopify Director)

So if you can have a good measurement rhythm, a lightweight planning rhythm—like a routine by which you pause and take stock and plan for the next period—and then an operating rhythm, if you can get that stuff in place, the engine will work pretty well.

Welcome back to another episode of the Revenue Reimagine Podcast. We have with us today a legend in his own right in the space: Kyle Nordon, who is the CRO of Owner.com, where he owns sales, partnerships, onboarding, success, support, revenue operations, and enablement. You have a little small job over there, Kyle. Kyle's also a limited partner at GTM Fund, Stage Two Capital advisor, angel investor. Spent a ton of time at Shopify, and he does a lot of work with SaaS-focused funds and startups where he shares insights and expertise on scaling, selling, and just as importantly, servicing SaaS products.

Kyle, thanks for joining, man.

Yeah, thanks for the invite. Looking forward to it. I'll try to live up to you.

You have a small little job at Owner.com. You run a department or two?

Yeah, yeah, exactly. How do you go from like a Shopify that you probably own a little bit of, to like Owner where you own a lot of it? And I think this will go into some of the conversations on frameworks and efficiencies. But you know, how do you make that jump?

I was pretty—it's funny, Adam and I were just talking about this before you jumped on—but I was historically a startup guy. I had never worked for a public company. My first company was maybe 250 people. Then I went into a true startup where I was Employee 26 for my first VP Sales gig. I did late-stage, late-stage private, and didn't think I could do a big public company. I was like, that's not for me. I don't want to work for a big company.

Then I was chatting with Jake Dunn and just getting his advice, and he's like, "Hey, we do this all the time as startup people. We say, 'Oh, no, startups are the only real thing. This is like the only career that matters.' And he's like, that's a silly way to think about it. You can learn a ton from seeing how a big scaled company operates."

So I went into those conversations with a much more open mind, and it was my boss from two jobs before that brought me into Shopify—made the introductions. And I loved it. I really like learning new things, and you learn a very different skill set. I learned how to operate in a very product-centric context. I learned how to partner better with product and speak that language, deal with a large matrix organization. So there was a ton of really interesting takeaways from that experience.

And now I'm back in a startup, but I feel very familiar with this. Even the job at Shopify was to build a new go-to-market engine within Shopify. My team was five people when I started, and then we grew it to like 80 people in 18 months. And then we reordered, and I went from this point-of-sale group to a regional mandate.

So yeah, I've bounced around. You've seen a little bit of change.

So we were talking before the show started, so fun fact for everyone: Kyle holds the job—the only job I've ever interviewed for and haven't gotten. And I was actually upset about it, having spent time at Toast. That's how much I believe in what you all are doing there.

But when you started, it was, I think, VP of Sales and Partnerships, right? It certainly wasn't CRO or VP Sales. We didn't have Partnerships yet.

Yeah, so you were just startup world leading a sales team—reps plus a manager—like a couple million bucks ARR?

Yeah, we were very small.

And you are what now? I don't know if you're willing to share the ARR, but how many reps? Like, how big is your team?

20-plus million. My team's about 100 now across sales and the other functions—partnerships, onboarding.

So that's a massive jump in a very short amount of time, right? What is different specifically about the growth that you have contributed to at Owner versus similar growth at Shopify? Like, big company in startup land versus like big company?

So five to 80 versus two to where you are now?

Yeah. Shopify was interesting because one of the really interesting philosophies that they have is to operate as a hundred-year company. We're here to build a hundred-year company, so they don't get caught up. Even for a public company, they don't get caught up in the quarter. You're indoctrinated in the onboarding: we don't pay attention to the stock price. We're here to drive value for the customer, and ultimately the market is a weighing machine—not a voting machine versus a weighing machine. And like, if you know that in the long term it's a weighing machine because the real value you're creating is what will be represented in the market cap.

And so the mandate I was given is like, "Hey, you've got like 80 headcount that's earmarked for you. Do what you want with it." I was like, "Oh, okay? Just I get that carte blanche. There's no gates. There's no 'this,' it's like 'Yeah.'"

We know that the point-of-sale product is good. We are confident that a sales motion is going to accelerate our growth based on some early learning. So go for it.

And so I could scale as fast as I thought we could go without things falling apart, and I could make upfront investments without needing to worry about the burn impact or, you know, overbuilding.

So I brought in enablement really early, revops really early. We grew those teams. I hired leaders that were like, you know, not really stage-appropriate. So like, one of my first managers was a former VP of Sales, and she would have never taken the role if I hadn't said, "Hey, look, the team is going to scale to this number in this period of time. The budget is committed. Come in to do the manager thing, and then I'll slot you into the second-line role." And then she became a VP of Sales for that group, and it happened in like an instant.

And I could just make so many forward-looking decisions because the budget was pre-committed.

At a startup, you know, we are still building with the future in mind and we're making investments ahead of time. You have to play a much finer balancing game of, you know, you don't want to overhire—make the mistake that so many companies have made over-hiring compared to your pipeline production or compared to the product maturity. And then you're doing like mini layoffs or RIFs, or you're in a tight burn situation. That's not a fun place to be.

So you're slightly more staged and gated in terms of those investments. But now, you know, like, we clearly have this extreme product-market fit. We know really closely the economics: we add this money to marketing, these people to sales, these BDRs here, and the output is so consistent over a 12-year time horizon. Now I can really—now we're hitting the gas, and we can do that with a predictability that gives us a lot of financial confidence.

Yeah, it's interesting. It's almost like every dollar you spend, you kind of know what that ROI is. So like, if I'm going to hire a new headcount, it's going to cost me $80,000. I know that return is going to be 240, 320 in revenue coming in the door. And I think that's where a lot of people—I've always had this thought: every person you hire should have an ROI number attached to them. But how do you get to that place is always a tricky place. It's just like going to the process, systems, and structure.

Yeah, you need systems and structure and infrastructure built so that you can build up a track record of, "Hey, I've got a 12-month history of: when we hire 10 BDRs, nine of them do really well. We promote a ton of them, and they produce a pretty consistent pipeline number."

Yeah. And where many businesses find themselves—where many startups find themselves—is you hire a handful of people, one person is ripping it right, two people are doing nothing, three... and then it's hard to pile a bunch of extra headcount into that system with a ton of confidence because you don't have repeatable playbooks in infrastructure.

And I think that's like a thing that we've tried to do well here.

What's been the hardest thing you've had to overcome in that scale? That scale is super quick. Like, the amount that you scaled in that time frame is a bit probably unnatural to many people that would be listening to this. So what was the most difficult thing that you overcame in that scale?

So one of the most important things to fix early on was onboarding. I inherited onboarding at some point, and it didn't have a lot of infrastructure. Yeah, it's great to be ripping in sales, but if a material portion of these people don't activate because we do month-to-month contracts, so they either don't activate or activate late or they're not set up properly, then this has a pretty significant impact on the business.

And I think what I try to do as a revenue leader is think really holistically about...

The business—and try to not get trapped into the sales number. I think this is a trap that many people fall into. You know, they feel like they're successful because the sales number is great, but the business isn't growing because churn is bad. Well, like half or more of churn is probably customer quality—certainly was for us—or how they were set up for success with the expectations that were set, or you know, the features that were demoed and where did we emphasize. So I think the biggest thing for me is to make sure that from top of funnel all the way through to customer value, we were running those parts of the business with the same intentional approach and proficiency. That was probably the biggest thing that I've spent the most time on the last little while.

So it's funny because I think we see this everywhere, and what you just described is perfect. It's what we see all the time—the sales leader or the CRO who only focuses on sales has no idea about marketing, has no idea about customer success. And it's like, "Oh, you know, we signed 100 deals in the past quarter, and that's great." Well, yeah, but 41 of them are still here. Like, that's not necessarily a good thing that you want to be proud of when you're scaling.

Kyle, when you're looking at stepping into that CRO role and owning the entire revenue number, like how do you determine where you're going to spend your time? And I want to piggyback that also with how do you direct your CEO's time? Because a lot of sales leaders that we speak with have no idea how to get the CEO to focus where they need to focus instead of what they think is important.

So there's two questions there. One is sort of the difference between an executive and a senior leader. So I think a sales leader thinks about their team first—they think about their team, the sales number, their compensation plan. It's relatively short-term oriented, and they are additive to the company. They're adding a lot, but an executive is a multiplier. So as opposed to thinking about their sales team, they think about the company first. Instead of thinking about their compensation plan, you're thinking about enterprise value. Instead of being short-term focused on the quarter and the pipeline you need, you're focused on long-term revenue quality. You have an understanding of the P&L, and that's what makes you a multiplier. That's what makes you a person that is able to create real enterprise value.

And this is the feedback that I get a lot from the board and my CEO—they appreciate the fact that I am not just thinking about the close-one number. And I think I get that feedback because it's not super common. They maybe don't see that all the time across the portfolio. So that's the distinction: Are you additive? Are you just bringing in the sales number? Or are you a multiplier? Are you a productive contributor to product conversations?

Who taught you? Who taught you to think that way? Because that's not normal, right? And you just said it—they don't see it all the time. Where did you have this epiphany? Or who taught you that? Like, man, it's not just about the closed deals. I'm not going to get where I want to go in my career that way.

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Yeah, there were two places. You know, when I became a first-time VP of Sales, I really tried to learn about building a SaaS business—what is this whole thing about? And like, not to be a total brown-noser, but I went so crazy deep on all things SaaS, and I learned so much from Lincoln before he was Founder. I was involved with them personally, but really trying to understand the broader picture. And Lincoln was one of the first guys that really talked about the importance of CS and how to think about that as a revenue engine. So I started to try to educate myself there because my first VP Sales job—I was not that well-rounded. I was really focused on the sales number, and I pushed product on whatever got me the sales number. I didn't have a churn-oriented view there.

So just general reading, and then I worked with a really good executive coach, Sky Pao, here in Toronto. And he pushed me to see the bigger picture. You know, like executive coaches do—it's like, "How do you think? What do you think that person thought about that? And how do you think they interpreted this?" And through this executive coaching work, I really came to understand: "Oh, yeah, you know, that probably isn't the right approach."

You know, as a salesperson, you're a competitor. Like, I'm a competitive psychopath, and that's why I was good at the job—because I want to win. But at the same time, you got to be able to turn that off when it comes to your teammates. I had to learn how to create win-win conversations as opposed to debates. When there was a strategic disagreement, I went into what Adam Grant would talk about as prosecutor and preacher mode. I would just hammer people with the data and my customer feedback, and try to beat them into submission. But you can't convince anybody of something in that scenario because now getting to the right answer—or what I perceive to be the right answer—means they have to lose the debate. And especially if you're a multi-time CEO or there's an age difference or there's just a power difference between VP Sales and CEO, you're very unlikely to win that battle because you've created a win-lose argument.

So I had to learn to get better at building a more constructive way to get to the right answer.

It's okay, Adam. We can get you to multiplier. We know you're additive right now. We can get you over to multiplier. It's all good. We'll train you up. We'll show you the way.

Yeah, listen, I'm good with it, Kyle. As the CRO in your evolution from being the VP Sales into the CRO and now seeing a cross go-to-market motion from marketing through CS and how product's running—what would you say are the top three things that new CROs should be looking at from a metrics perspective that would help drive their business?

Outside of the sales stuff, you mean? It could be anything through the go-to-market. Like, is it lead conversion? Is it deal velocity? Like, what are the metrics that you're really keen on right now?

There's not three. There's more like 30.

Okay, sure. So let me just highlight some of the things that I think people miss. You know, because I think we're all looking at our funnel and breaking it down by AQL to book, book to show, show to demo, hold, close rates. Like, I think we do a pretty good job of that. But I think where people could spend more time—if you want to position yourself to be like an executive, like, I'm a productive contributor, even if you're just the VP of Sales but want to be seen in that light—I think the thing is to go deep on churn and understand what part of churn is driven by sales—either expectation setting, handoff quality, customer quality. Like, are these the right people that have the right problem for us to solve? Because if you close a deal and it turns in 12 months, that's not good. It's better to not have had that revenue at all.

Yeah, it actually costs you money. The net gain is negative. What's the return? It's at least 18 months, right? If you're good.

Yeah, 18-month payback period. Lots of companies would love that. But it could be 24, 36 months. And so, let alone talking about—well, if 33—at Toast, Kyle, when I was there—but who's counting?

If they really calculate CAC properly—I mean, who's calculating CAC properly?

Yeah. And like, it works for Toast because you've got this other suite of products and you're expanding and all that stuff. But so, I think like revenue leaders—if you want to be taken super seriously by your CEO and have your opinion valued—you have to be able to speak about the business broader than just sales. So a super deep understanding of churn, and especially understanding what role sales plays in that churn, and then own it. Just be like, "Hey, I looked at a bunch of this stuff. This is on me. My team is closing some questionable deals, or we need to do better." And go spend the time shoring that stuff up.

Yeah. So a really deep understanding of churn would be...

# Transcript

**Number one: Efficiency.** I think this was a big difference between first-time VPs sales me versus now. I'm like, "Yeah, more reps. Let's hire more reps. Let's get more bodies in here." We collectively built a model that was way too optimistic, and we ended up having a layoff of like 25% of the sales team at some point because we just didn't have the pipeline to feed that team.

So being more efficiency-focused, understanding your unit economics, payback period, CAC, LTV, how do all these things play together? And can you understand it by channel? So is your inbound channel really efficient but your outbound channel is a mess? Okay, then how do you go improve efficiency there?

And the final thing would just be like holistic P&L—holistic understanding of the P&L or just forecasting in general, right? Not from the top-down but maybe more bottoms-up forecasting.

Yeah, yeah. And when I say P&L, I mean the profit and loss statement, the income statement. To really understand: all right, like how does this whole machine work and what are the levers that drive growth?

Because what oftentimes as revenue leaders we don't understand is like the changing churn has such an exponential impact on the business. And maybe that is where you should spend an entire quarter versus something else. Or maybe, you know, by understanding the P&L and really looking at like the cost of the events that you've been running—oh, we only generated this much revenue and this much revenue turned in this period. So the return on those things—I think just general financial and P&L fluency is another place that, if you want to make that true side jump, is important.

Yeah, I was typing notes. I don't do that a lot during our shows, but I'm literally typing notes. This is recorded. You can go back and listen to it. It won't hurt you. I understand, but it's easier for me to remember if I take the notes at the same time.

Kyle, what's your opinion on—and I totally agree with you—I don't think enough people understand churn as it relates to sales or even one more step up: marketing. Like, is it really the right ICP that we're selling into? Because that drip-down from marketing into sales, you get into a domino effect. If it's wrong at the top, then it's gonna be wrong in the middle and it's going to be really wrong at the end and cost you a lot of money. But what's your opinion on looking at NRR or NDR versus churn from like a metric to pin your hat on?

It's all important. Like, you got to look at gross and net. If you only look at one, you're going to miss some of the picture. Because your NRR could look good because you've got two or three customers that have expanded like crazy, but then from a logo count perspective you've bled 20% of your customers. And that will give you different signal.

It's all about triangulation. Like, it's hard because you don't want to look at every single metric and get lost in it. But at the same time, you want to figure out: what are your absolute must-move metrics?

My VP Sales, Brett, he talks about with his team: biggest needle movers this week, this month. What is your number one biggest needle mover? And so we're combing through in our monthly business review process everything we look at—like every piece of data across the team—and then go find the thing that we want to spend the most time on and then we go really deep on it.

So by going through net versus gross churn, NRR versus NDR versus GRR, you can start to pick up these patterns. And then you just pick that one thing and tackle it over some period of time. So you don't have to constantly juggle 100 metrics.

Yeah, but it's in some cadence. For us it's monthly because we're SMB high velocity, but for many businesses it's like once a quarter you really go through everything. And then let that direct you to the can't-miss metrics.

So like in my SLT—in my SLT meeting agenda—there's a section of it in Notion that stays there every week, which is like the can't-miss metrics. These are the things that we care about right now. So I don't care about close rate right now. We feel great, we feel good about close rate. We've moved close rate significantly a couple quarters ago. But like the one thing is whatever. And like we look at that thing every single week to track against it.

That's a good way to take this pretty overwhelming cloud of data and try to thin it down to something that drives more action.

Love it. If memory serves me right, you actually shared your business review template on LinkedIn like a week or two ago. I think you shared like a massive Notion document of like every metric that everyone looks at and that you have your teams report on?

Yeah, I think I shared like six different Notion templates on my Substack. I gave a talk at SaaSter which should be up—the recording should be up in a week or two—and I went through what I call my Revenue Operating System, or Revenue OS. Thanks to Brandon Gayle for that name. But I shared this whole Revenue OS which is a breakdown of like how I run the team, how I communicate the metrics. And then I made template versions of everything. So you can go to the Substack, the Revenue Leadership Podcast. I actually literally have it in a window on my screen.

Good. Nice. True story. And so everyone doesn't think that I'm lying. I'm writing a newsletter on this topic of the difference between executives and senior leaders. So now I got to figure out how to stop. All right, there we go.

So that's super cool. I love the giving back. It's something that's important to us as well. And the fact that you're willing to share that and make other people better, I think is huge.

Kyle, we work with and we talk to a lot of founders—maybe first-time, maybe second-time C-level—with the passion you have specifically for frameworks and infrastructure, when they're trying to build out for the very first time a real go-to-market motion. Where would you tell them are the top things? Like, you got to start here. You can't freaking go here unless you start here?

Yeah, so this is on my Substack, my Revenue Operating System. I wrote a whole massive page on this, and so you can get it in a lot more detail.

But it starts with the measurement cadence. Like, your ability to understand what's actually happening in the business—if you can't understand and you don't have the right infrastructure to capture what's happening on the front lines, then you can't do anything really.

So you need the right data collected in a lightweight, structured manner. You need a cadence to review that data. Then you need a planning rhythm—like a light planning rhythm. So each month, how do you synthesize what's happened and make sense of it and make decisions about what's going to happen in the next month? That's like the planning rhythm.

And then the final piece would be like your team rhythms. So how do you operate day-to-day? We do our weekly standup and we cover these things, and here's the template for our meeting. And then every week I want a written summary. And I use this thing called MAPLE: Metrics Advanced, Planned, Learnings, Emergencies.

So what did you do that week? Planned. What are you planning to do the next week? Learnings and Emergencies. Maple. And my senior leaders all fill out a MAPLE update that I review on Sunday nights, and it powers what we do in our one-on-ones and what we want to talk about in team conversations.

So if you can have a good measurement rhythm, a lightweight planning rhythm—like a routine by which you pause and take stock and plan for the next period—and then an operating rhythm, so how you want to engage as a team—a template for your one-on-ones (and there's a template linked in that page), a template for your team meetings, a template for your weekly update—if you can get that stuff in place, the engine will work pretty well.

What was the E in MAPLE? Emergencies?

It's like emergencies are just stuff that's important, but stuff that's important didn't make MAPLE. So E might be like a little alarmist, but yeah, it's like things. Sometimes alarmist is needed. Like, listen, everything can't be an emergency and everything can't be a fire. But there are things that, like, hey, it might not be in one of these categories, but dude, I got to discuss this with you before we get off this Zoom.

And I like MAPLE. I like these mnemonics and anagrams and silly things like MAPLE or like our can't-miss metrics or Kyle's top 10. I name all of these things so that they're memorable. And when I say, hey, like we got to do this or we got to do that, like everybody knows what it is and we can sort of teach people around it. It's like common language.

Yeah, yeah, yeah. Yeah, it could be OKRs and you...

# Cleaned Transcript

You can call it whatever you want, but just having a common language makes things run a little more smoothly, man. I wish we had 90 more minutes. There is so much I would like to plug you in for another 90 minutes. We are definitely going to have to find a time for a V2, but as we wrap it up, as we do with everyone, I'd love it if you're game to throw some rapid fire at you, man.

Let's do it.

All right, early bird and night owl. I was a night owl, now I'm an early bird. Is that because of kids?

Is that because of the hours in San Francisco?

Mostly because of kids. Yeah, that'll get you every time. Then you just become an early bird for the rest of your life.

Yeah, exactly.

If you weren't in tech, what other industry or something else would you be in?

Trade? I have no idea. Musician, sports person? I like what I do. I would love to say professional athlete, but I'm not that physically gifted, so that's a poor answer. I almost went to fine arts school. I went to business school, but I was a hair away from going into fine arts school, so maybe I'd be a sculptor. Sculpture was like my thing.

Okay, nice. Kyle, what's your favorite guilty pleasure snack, man?

Wings or salt and vinegar chips.

The wings, I'm with you on, man. Can't do the salt and vinegar.

Oh, the best.

What's the most used work emoji in Slack, text, etc.?

Probably the handshake.

Makes sense. All right, two more. Other than your iPhone—I hope you use an iPhone—but other than your phone, what's the one tech gadget you can't live without?

AirPods for sure. I listen to, according to my Spotify wrapped, 54,000 minutes of podcasts last year.

Wow, like two hours a day?

Yeah, I mean when I work out, when I wash dishes, when I'm doing chores, I got a podcast going or an audiobook. So you're a true lifelong learner then? Like it's all about learning constantly.

I'm addicted.

That's awesome, man. My wife likes to tease me. She's like, you love tidbits, just tidbits about stuff, anything and everything. I like to learn about, and that's why I started my own podcast because I'm like, I gotta—I think I can do something here. I listened to enough. I gotta—part of Top Line and Pavilion, right? Part of the pod.

I love that.

Last one as we wrap it up: dream vacation destination?

I like adventure vacations. Japan was the best vacation I've ever been on. I would say my wife and I did that right before having kids, but anything like wilderness adventure, far-flung places. Yeah, probably something like mountaineering in the Alps would be up there for me right now. I've never done that.

Love that. That's awesome. We—my dream is an African safari. So I'm with you with—that was our honeymoon and it was the second best trip we've ever done. It was amazing.

So jealous. Felt like you were in Jurassic Park. It was a crazy experience.

Kyle, thank you so much for joining, man. Go check Kyle out on LinkedIn if you are a small and medium restaurant owner. Check out Owner.com. The absolute best restaurant tech you can find. Kyle, thanks for joining the show, man.

Thanks for having me, appreciate it, man.