Kyle Norton has led sales teams at two unicorn companies — League and Shopify.
While leading sales at League, he grew revenue to $20 million and scaled their sales team to 40 reps.
3 years later, he joined Shopify as Head of Revenue for their retail division to help roll out their point-of-sale products.
In today's episode, Kyle joins Alex to discuss:
Alex Kracov: I'd love to start today's conversation with your time at League, a health insurance startup. You joined league as a VP of Sales, and the company had just raised a Series A. What made you join League?
Kyle Norton: So it was an unorthodox Series A because there was no SaaS revenue yet, and the company was going through a huge pivot. But they were able to raise $25 million basically on the back of the founder. It was a third-time founder. He had sold his first two companies for hundreds of millions of dollars. And in Canada, that was very much a rarity. And so that's largely what I was drawn towards. I've always had a passion for health, frustrations about our healthcare landscape. The opportunity to work with a proven multi-time founder was really attractive, because I have never been in a true startup before. So it was really about the learning opportunity.
Alex Kracov: What was the company like when you joined? You mentioned there's this transition from, I guess, a non-subscription revenue. What was the state of the sales team? Can you paint a picture?
Kyle Norton: Yeah, so there was no real sales team. There was a few people doing some selling and some CS but for our like Uber for massages-type motion. They were trying to sell to big employers to get them to basically book services through our app. But we were transitioning to being a full healthcare provider for employers, an insurtech. So I was building the sales motion from scratch.
Originally, we were going to have three motions field, an inside motion that I was building and then a partner motion. The other two motions didn't really take. And so, basically, what I had built as the inside motion became the only thing that we did. So it was just me. I hired a small handful of reps, a manager from my network. We were just going at it with this brand-new messaging, brand new product, that sort of know we didn't have any customers on. We're just trying to get the first real deals, which is a weird thing. Because you find that product-market fit when you're a five-person company on a pre-seed round. We were trying to do it as a 30-person company. And so the pacing wasn't pretty different.
Alex Kracov: Yeah, it gets way harder to move when you have a much bigger team. More people you got to explain things too. It can't be as nimble. I'd love to go a level deeper there. How did you go about evolving that sales pitch in the process, even though you're a little bit more of a mature company? Was there founder-led sales that you were sort of building off of? How did that kind of work?
Kyle Norton: Yeah, so there was a lot of friends of the founder. We called them FOMs - friends of Mike. The sales team was doing all the pitching. We had Mike in some of our really big deals. But for the most part, we were just out there trying to make it happen. He would do sort of board engagements, or he would go over the top to the other founder. Because we were focused on selling into mid-market technology companies at first because they would be more forward-thinking about health care.
And so the iteration was really rapid. We were recreating decks basically on a weekly basis ourselves. We had one AE who's awesome in Photoshop and PowerPoint at the time. So we were just on our own iterating like, oh, we said this. We tried it this way. That got not the right response, so then we would redraft slides every week and then try to go out the next week and say something a little different. It took us a while to get to the right messaging that unified what the buyer cared about and what we could actually do in our vision. But it was very much a challenge our model where we were trying to get people to do something really different. So finding the way that we could communicate that message, while also not scaring folks off, was the tricky balance.
Alex Kracov: Over the three years I think you're at League, you grew revenue to $20 million plus and scaled the sales team to, I think, around 40 reps. Was there a moment where it started to feel like things were working, or were you always just sort of pushing a ball up the hill, and it was hard? How did you sort of feel about it?
Kyle Norton: Yeah, I always joke with the folks that I worked with in that era like, no, I never felt like it was getting easier. One of the interesting things about raising that amount of money and having those expectations is, you just have to grow so fast to keep up with the expectation of that financing. That as we started to get a pretty decent fit in particular markets, okay, we've got some good mid-market references. We're starting to build a name for ourselves there. Then it was like, alright. The company target goes up 3x next year. So we couldn't possibly do enough of those deals. So now we have to do only enterprise.
It was the amount of money raised and the expectations ratcheting up so quickly that really drove us to need to chase up market. Ultimately, that wasn't really the right decision. It was a significant struggle for us to win deals in markets where we had no references. We're pitching at 5,000-person company, and our most referenceable customer is 400 people. It was really, really difficult, and every deal was brute force. Every deal, you were having executives go over the top and pulling levers at their board level. We were multithreading all over the place and every deal had to be run picture perfect throughout. So you are losing. It never really felt like it was getting easier. They've since evolved away from that employer product and sell a more insurance platform product. So we never really got product-market fit in a true sense.
Alex Kracov: It's so interesting, the relationship between financing and capital raise and your go-to-market strategy and the expectations there. It sounds like you're forced to just do a bunch of inorganic things away from product-market fit to go chase those big goals. And yeah, I don't know. It's a thing that I think about a lot as we build Dock, to keep our valuation in check so we have reasonable goals. Because I think companies grow at a really - there's a natural growth rate to a company into an expanding market. And if you try and force it too much, it doesn't always work. Sometimes, it works. But I don't know. It's a tricky balance.
Kyle Norton: Yeah, especially true in disruptive technologies where you're trying to convince the market to do something different. So we were really trying to get employers to think about how they delivered healthcare and insurance to their employees in a very different way. The market just needs to mature. People need a little bit of time. I think one of the product-market fit challenges was being early. And so this problem of raising too much money wasn't really a thing in 2016. That didn't happen. It happened in 2019, 2020 where, as a founder, sometimes you'd have to say, actually, we're going to raise a more reasonable round. That dynamic, I don't think existed pre-2018. But we found ourselves there. And it was a tremendous lesson for me to learn. I share this lesson a lot with founders who I advise. Because it can be painful for sure. It makes you make short-term decisions that are not productive long term.
Alex Kracov: And so after League, you joined Shopify as the Head of Revenue for Retail. What made you make this move, from a Series B startup to an established public company?
Kyle Norton: I never thought I would go to a big company. Like many of us thought, the only real company building is in startups. That's the real stuff. Big companies are slow, and it's easy. Why would you want to go do that? Actually, a friend of mine, Jake Dunlop, I reached out to him just for some advice on it. He gave me a little bit of a come-to-Jesus talk. He was like, hey. He's like, you and me, startup guys, we assume that that's the only thing that is out there. But going to a big company, you learn a completely different set of skills and pattern recognition and mental models. He's like, you should think about getting that type of exposure. It was a blend of both. I got to go to the biggest, most successful tech company in Canada, which was exciting. But also, I get to build a new thing, like a new go-to-market motion for the point-of-sale product. So it was the best of both worlds. I loved it. I loved my three years there. I learned a tremendous amount and very different things than I learned in a startup. So I strongly encourage people to think outside the box if you consider yourself a startup person.
Alex Kracov: And so you mentioned when you joined, Shopify was rolling out this point of sales product to retail vendors, and you were put in charge of selling that solution. So kind of like a startup within a big company, if you will. Can you talk about the point of sales product, and how you approached sales? I mean, were you competing against Square and things in people's actual offices?
Kyle Norton: Yeah, so Square, LightSpeed, Vend. Yeah, the product that you're checking out with when you're at a clothing store, for example. And so the product was fairly well-established downmarket. There was $70 million in revenue in this business, so it wasn't nothing. But we were really just piloting a farther upmarket, human-led go-to-market motion on top of the self-serve motion that already existed. And so we grew the team from 5 people to 70 and changed in 18 months. Really moved the needle on the growth rate for that business and had a blast. It was a really exciting opportunity. I largely joined that team because the guy who ran it, Ian Black, I thought I could learn a lot from. He's a former senior Uber guy, super smart dude and was clearly going to do something exciting with that business. The product was great, and it was the opportunity to go build. So I had no regrets about it. I loved my time there.
Alex Kracov: What did sales actually look like? Are you selling into just existing Shopify customers who already have a Shopify website? Do you knock on doors? Do you do cold calling? How do you sort of approach it?
Kyle Norton: Yeah, it was a lot of expanding into the current Shopify base. We had a bunch of data to give us a likelihood that that e-commerce customer had a brick-and-mortar location, using a bunch of the Google API data and other stuff to take a best guess. That was the first nine months. Then COVID hit. All of a sudden, every business in the country needed to have an online motion even if they weren't all ready. And so the business ended up shifting from probably 80% expanding current customers with point of sale to almost 50-50 current customers expanding to new customers wanting to get set up online and then us saying, hey, if you're a brick and mortar, your brick and mortar is going to be closed. Move the whole business over now, so you have one system of record, one platform. Then when you're ready to open up again, you have a better place to deliver an omnichannel experience to your customers and grow faster. The motion changed a lot in COVID. We had to rebuild all the messaging and retrain folks. That was a pretty wild time.
Alex Kracov: I want to get into COVID a little bit more in a second here. But staying on the pitch, why were customers buying this? I assume it's the tie in to the website and the Shopify platform. Is this omnichannel? Was that the pitch? How were you able to go against Square, for example, or whoever the competition was?
Kyle Norton: Yeah, you're right on it. The point of sale feature to feature was either behind or just at parity. But the fact that the point of sale was attached to this ecosystem, the best e-commerce product, all this other tooling, and you could unify both the operations of the business so it's easier to operate if you're running Shopify across the business versus having something integrated or unintegrated, that was a piece of it. Also, it unlocked so many multi-channel marketing opportunities. Being able to have one customer record so that you can understand buying patterns. You could market to people who buy online to drive them in store. You can remarket to people who come in store because now you're capturing their data at checkout, and then get them to buy online. And so a lot of the data showed that if you can have somebody purchase online and offline, their stickiness was tremendously elevated. And so that was the pitch. Make more money. Simplify your business, and also be future-proofed. Shopify had shipped features and developed it at such a pace above and beyond everything else that you're saying, like, look, you know that this market is changing. You know that the customer is changing. So pick the partner that is going to be ahead of the curve. That was another big part of the positioning.
Largely, to tie League and Shopify together, we would use what I call a point of view positioning. And so this helps you really quickly let a customer opt in or opt out and qualify them upfront, and then build a lot of trust by saying like, hey, look. We're not the perfect product if you care more about inventory management and analytics and reporting. Our reporting is not as good as Lightspeed. And so if that's the most important thing for you, it's probably not us. But if you believe that in order to win in the next couple of years, you need to be able to service people online and offline, and they need a great online experience, then Shopify is sort of your only choice. Then that would let customers really quickly say like, yes, that's what I believe. So I should evaluate it. We did the same thing at League. If you believe X and Y about healthcare and what's wrong with it, then we should talk. It's a great way to build massive trust upfront and also just get the wrong people out of your funnel fast.
Alex Kracov: I love that point of view positioning because you're trying to lead them into the future. It's like anybody who's innovative and thinking about the future feel like they have to say yes to that point of view, right? As a retailer, you'd be all thinking.
Kyle Norton: Yeah, you'd be surprise. We would joke at League. If we could run a LinkedIn search algorithm to just find all the people that were wearing tech fleece hoodies and disqualify anybody who's wearing a blouse or a tie in their LinkedIn profile, that's how we should prospect. It was a little bit of a joke, but there's a lot of truth to it. Because we would pitch to somebody who has a very old school view of HR. It's risk management. It's legal. It's sort of like parenting your employees versus a more forward-thinking HR leader who understands, hey, healthcare is important for people. And if we can deliver this type of experience, they can be better healthcare consumers. It'll drive down costs. Some people just couldn't compute what we wanted to do. That was okay. The key was how to qualify them out as fast as possible. Point of view positioning was a great tool to do that.
Alex Kracov: Yeah, as I was researching for this interview, I was even surprised that Shopify even has a sales team. Shopify has such an amazing self-serve product-led growth business. Can you explain a little bit how is sales organized at Shopify? Because I know after you did the point of solution stuff, you ended up leading go-to-market for Canada. What does the sales look like at Shopify more broadly?
Kyle Norton: You're opening up Pandora's box with that question because it's changed so many times. There was a plus sales team selling the upmarket product. To customers with a million in GMV and above, there was a more sophisticated product. And so they had a sales team. That organization was probably 4 to 600 people before I started, but we didn't crossover at any point on the org chart. We were totally separate product lines. I was building something separate.
Then after the end of 2021, no, the end of 2020, we brought all of those teams together, regionalized. Every region sold all products. It was basically a train wreck. Not the right org design, bunch of weird decisions made. And so we sort of floundered for 12 to 18 months and tried to unwind that reorg incrementally. Because we over regionalized. We had duplicates of roles everywhere, really poor collaboration. And so that was a big challenge. And so we unwound a lot of that. A new CRO just joined. This guy, Bobby Morrison, I think his name is, from Intuit, he's whipped the place into shape. So now there's a lot more central specialization, a services model. They've brought back the retail team. My team got disbanded, which crushed me at the time. It was really sad to see. Now it's back as a thing. So what's old is new again. It's ebbed and flowed a lot. But it seems like in the last couple quarters since Bobby has got his people in there and he's making decisions, it seems like it's on an exciting pace, which is exciting for me because I'm a big Shopify fan. I'm super, super excited to hear that it's really clipping now.
Alex Kracov: It's an amazing company. Toby is just such an incredible, aspirational leader I look up to so much. But yeah, it's so interesting to hear org redesigned, stuff. Yeah, I could totally see how there's a lot of duplicative roles and how the GM model probably sounds good in theory. But in practice, it's like, okay. Now I'm hiring two of everything, and no one has actually specialized at anything. Yeah, it's interesting balance.
Kyle Norton: It sounded cool and it sounded like - I actually never liked it on paper. I wrote an eight-page document arguing against it. That didn't go anywhere. On paper, I got what they were thinking. But then in reality, it didn't totally make sense. Then the guy who was behind it left the business four months after it happened, so we were all left doing cleanup duty. Lesson learned. Again, it's frustrating at the time. But lots of interesting lessons in terms of great organizational design and how you can build high-functioning businesses. Yeah, but it was wild.
Alex Kracov: I'm curious how does Shopify sales teams sort of play off of that strong product-led motion. Are there triggers that you have, or it's like, okay, time for the sales team to reach out to this customer? Or, are you reaching out to net new people who have never even built in Shopify before? What's the balance there?
Kyle Norton: For a company of that size, we were actually a lot less sophisticated than you would think in terms of the use of data for go-to-market. On the product side, very high sophistication. That growth organization is probably one of the best in the world. Luc Levesque, who runs it and really piloted it, he's a badass. But we never really got that same level of sophistication in go-to-market. And so you did a lot through the tools that you did have access to, but a lot of that happened at the team level. The advantage was, you had a lot of customers that were growing quickly on Shopify's core products, and we had great data on those customers to try to upgrade them. Then on the sales side, everybody knew the best targets in their market. They're on our competitors. They are the brands that people know about. And so the prospect data was a little messy. They've just relaunched their whole Salesforce instance. I think that's getting better, but that wasn't our forte. RevOps wasn't our forte until, I think, recently.
Alex Kracov: Yeah, I think companies with amazing product-market fit, a lot of the times, the internal operations, you can get away with it for a lot longer than you think. I know Stripe had a similar situation. I've talked to people there. But yeah, I mean, when you have a great product-market fit, it covers up a lot of stuff.
Kyle Norton: Yeah, and you just have so much inbound volume. There's so much inbound volume, and the outbound conversion rates are so strong. Because it's Shopify. People are like yeah, I'll take a meeting. Yeah, tell me what's going on. What are you guys building? There was a genuine curiosity from customers to hear our point of view and what's going on, especially product-wise. So, yeah, that definitely leads to not needing to be crazy buttoned up. But that was a tremendous opportunity. I think now that the company is building a lot of go-to-market strength and a lot of go-to-market sophistication, that business will accelerate in a significant way. Because there is so much opportunity, so much data, so as the brand and power is so great. Their product is just unequivocally better than basically anything else out there for most pure DSC use cases. So I'm bullish.
Alex Kracov: You mentioned Shopify was uniquely impacted by COVID. First, there was all the uncertainty around small businesses and shipping. But then, Shopify experienced insane growth during the pandemic years. What was that experience like for you on the ground there, and how did that change how you approach coaching reps?
Kyle Norton: Yeah, it was just a blur, especially because I was in this point-of-sale group nine months into my role when it all happened. The entire team was under four months of tenure. And so we were on the fly changing stuff almost every day. We thought our business was going to just be eviscerated. We'd said, everybody, we're going to guarantee your full comp. We're going to pause the variable compensation plan. We're just going to pay you your full OTE. You're well taken care of. That was a very Shopify approach to things - taking care of people and doing the right thing.
But then, a couple days later, a couple weeks later, all of a sudden, we got the most insane inbound volume as all of these people were trying to figure out how are they going to survive as a brick-and-mortar business. We were the default choice. So we had to quickly pivot into a mode of, how do we just deal with this volume of inbound? How do we now pitch this new customer type that wants to move their whole business over to us? We were changing messaging and checking in on people a lot because people were just so busy. The Zooms of the world just fielding mass volume.
I think the thing that we did well there as a leadership team is trying to make decisions from the viewpoint of the customer. It's like, what does the customer really need from us right now? How do we deliver that at scale even if resources are relatively limited? That was a very Shopify set of values. It's like, deliver massive customer value is priority number one. Make money by doing that. And never forget, don't confuse one and two. And so the customer centricity and how you're enabled at Shopify to actually make customer-centric decisions was, I think, the best thing that we could have done at that point. Every decision we made, it's like, okay, well, how does this affect customers? Does this let us serve more people? Does this let us get people, help people faster? And so every week, we were making changes and updates and changing qualification criteria to help more people. It was a good lesson in customer centricity. Massive numbers of those businesses are still in Shopify today and thriving.
Alex Kracov: Switching gears a little bit. Now you're working at a startup called Owner as the SVP of Sales and Partnerships. What made you leave Shopify? Maybe a better question is, what about Owner that made you want to go do another early-stage startup?
Kyle Norton: I said I would never go back to early stage after League. I was like, that's too crazy. I just had my second kid. I was really happy at Shopify. I had no intention of leaving. But one of the venture capital funds I'm involved in, GTM Fund, invested in Owner. And so, through that process, I met the founder, Adam. We ended up being on calls every week. There was just a magic there. I was doing some advisory stuff. At some point, Adam was like, hey, I know you're not really looking around but - he's like, would you consider exploring, joining us full time? I'm like, oh, I don't know. The time is not right. Maybe in September timeframe. As I started to learn more about the business and spent more time with Adam, I just came to the realization. I was like, my philosophy on investing is like it's all about the founder. Yeah, you want a big market. But Uber was black cars for rich people, and now it's just logistics. PayPal was payments for eBay, and now it's this massive fin tech platform. Okay. So market can change. If we think, market, product, team are the three variables. Market can change. Product can definitely change. Good products can catch up, and it can get better. Great products can lose a step. But really, what's the thing that determines success? It's just like, is that founder truly elite?
As I've learned more about early stage, it's not just about being a great founder. I think great maybe gets you to a Series B or something. But to really go do something special, you need to be truly different, truly world class. That's what I saw in Adam. It was sort of FOMO more than anything. I was like, I can fast forward this movie three or five years. I can see myself being on LinkedIn seeing some insane announcement from this company and being like, wow. I could have been there. I missed out even though I knew that this guy had some magic. Adam and Dean, the two co-founders, I was just I'm insanely impressed with. And so I just sort of felt like I had to do it. I couldn't miss this opportunity. Because they come around so infrequently. I have never met a guy like him, ever in all of my investing advisory or just being involved with startups. I have never really been around two co-founders that have the discipline and drive and learning motor. The two of them were just insane learning machines. So I jumped in. Even though the timing couldn't be worse. My son was three months old. Personally, it was a very challenging six months with two young kids. But I'm very glad I made that decision because it's been an awesome ride, and I'm very optimistic about where we're going.
Alex Kracov: Yeah, Adam Guild is super impressive. I mean, I had a 30-minute, an hour call with him talking about marketing. Everything you just said resonated with me. I was like, oh, wow. This guy is an amazing learning machine and just very unique. He is also very young, which is interesting. What is maybe his first real company he's ever worked at? What has it been like working with Adam to build out sales at Owner? What has that transition been like from founder-led sales to sales-led sales?
Kyle Norton: I'll separate those two questions. Yeah, the learning machine thing was what caught my attention. I remember it so clearly. We were talking on a call about messaging. I was like, oh, I really liked this book Made to Stick. It's got some good frameworks to just simplify things for customers to better understand. Then 18 hours later, he texts me. He's like, hey, I read that book. One, it was impressive that he just read this book I mentioned offhand in 18 hours. Then two, he just started asking me these questions. Not clarifying questions. They were questions I would expect to get from a seasoned go-to-market operator that's been doing this forever. It's like, Jesus Christ. He just read this book, and he has clearly synthesized this information so massively. And so I think that is his superpower.
Your other question was about, as a first-time founder, that ability to learn incredibly rapidly means that we don't need to learn as many of those painful for some founder lessons as you otherwise would. Because that super learning, combined with an intellectual humility, avoids a lot of those mistakes. He has a good network. He reads voraciously. And if it's go-to-market stuff, when I share my opinion, he's really open and interested in it and is genuinely inquisitive and curious. He's like, oh, how do you think about that? What about this? And even if we have a disagreement and we're talking it through, if my logic is sound, he's like, okay. Great. That sounds like the right decision. Let's do it that way. The humility and lack of ego to not need to be right every single time or not need to do it my way is way more rare than it should be. That allows him to operate way beyond any first-time founder that I've been around personally.
Alex Kracov: Can you explain a little bit about what is Owner and maybe how has the sales pitch evolved, if it has, from when you started to what it is today?
Kyle Norton: Yeah, so the core problem we solve - I'll answer this from the restaurant's perspective first. The core problem we solve is, over the last five to seven years, the guest has changed a lot. Now digital ordering is not just a trend but it's very much an expectation. Uber Eats, obviously, the third-party marketplaces, in general, were gaining a lot of prominence. Then COVID sent it from clear trend to basically an overnight absolute. My parents can use Uber Eats. And if my parents are using Uber Eats, it's a wrap. They're not exactly the world's best technologists.
That means, for restaurant owners, they need to be able to deliver not only good food and service but a great digital experience. They need to be able to be found online and have a good website. That's definitely not in the core competencies of 98% of restaurant owners. They got into that business because they love food. They didn't get into the restaurant business to be digital marketers. And so they oftentimes are trying to keep up with the customer by cobbling together a Wix website and use ChowNow for ordering. Then they'll use like a text provider and MailChimp for emails. They put it all together. They don't do an awesome job. Then they basically get nowhere. Their customers are still buying from Uber Eats, where they're paying a 30% commission. It just leaves them insanely frustrated and actually losing money.
And so, Owner, out of the box, solves that whole problem. And so we provide them a website, an online ordering experience, so people can actually order directly from them. We API back into delivery networks, so they can still get the delivery drivers even if they don't want to deliver in-house. Then email and text message marketing tools, loyalty program. We custom-branded app for every customer. It's all wired up with AI, so AI will assist them if they want to write a custom email or create campaigns. We've got a bunch of cool AI stuff that we're releasing over the next little while. The outcome is, they make way more money. Oftentimes, we're doubling our customer's direct delivery business in 90 days, which is super cool. They do way less of the stuff they don't want to do. They now let us do all of the heavy lifting on digital marketing, and their business is way more profitable. It's cool to support small business in this way. If you go read our G2 page, for example, everybody says the same story. It's like, "Man, I was stressed. I hated trying to do this on my own, and now I'm making all this money." That's super fulfilling.
Alex Kracov: Restaurants are a super tough market. I mean, I started my career selling sales at Yelp and cold called restaurants. I feel like they've been burned by so many vendors in the past. They've been thrown - I mean, you mentioned a few. Wix, ChowNow, and then you got DoorDash, Uber Eats. How were you able to stand out and build trust as you work with these restaurants? Because as you said, they're not amazing technologists. I feel like they're skeptical as you reach out. It's like, hey, we're going to solve all your problems, and we're going to save your money.
Kyle Norton: They've definitely heard all of that before, and they don't believe a word you're saying. Yeah, 100%. They have every right to be skeptical because they've gotten sold a bad bill of goods a lot. There's two things. One is the sales experience, and two is sort of how we contract and interact with the customer. I'll start with the contracting because it's a little straightforward. We don't do long-term contracts. So every customer signs up with us month to month. If they don't like it, they leave. We will give them all of their customer data that can one click export. We'll help them revert back to their old website. So we're really lowering the stakes of making a mistake for the customer, and showing them it's okay. We're going to put our money where our mouth is. If we don't give you a great result, we're going to make it super easy to walk away. And so you have to have some trust that we can deliver. Or else, we'd get crushed as a business if we made it easy to walk away. Even in the early days, we had a money back guarantee on top of that. We pulled that away because we don't need it. It reduced customer commitment. But we act with a lot of transparency and customer centricity. We make it easy to do business with an easy to walk away.
But then, on the positioning side, going back to that point of view positioning, I have a radically transparent sales style. And so I want my reps to tell customers what's good and what's not good about Owner. And so the tradeoff that we architect for a prospect was like, hey, look. No product is perfect. That doesn't exist. Every product has advantages and disadvantages. The disadvantage, the tradeoff of using Owner, is you're going to get a lot less choice and customization. Your website is going to be our core template. We're going to build the email journeys for you. You don't really get to choose the order and how those things look like. We're going to change the style and the comp copy. But you're going to have to fit into a box with Owner because we know that these are highly optimized templates and patterns that are going to work and deliver results, deliver revenue for you. But in exchange for giving up flexibility and choice, you're going to make way more money. You're going to do way less work, and your life is going to be better.
And so if you care more about design and aesthetic, and you've got a brand guide that you had some marketing partner do, and that's what you care about the most, don't use us. Choose BentoBox. It'll cost you way more, but you can make it look super pretty and all this stuff. But if you just want results, if you just want to make money, then we're the choice. That level of transparency, again, just lets the right people opt in and be like, "That's exactly what I want. I don't want to do any of this crap." Okay. Cool. Your trust goes way up, and your buyer can opt in faster and vice versa. The people, it's like, oh, wait. So I can't do my custom fonts? No, you absolutely can't do your custom fonts. Okay. Cool. Then it's not a fit. Great. Cool. No big deal.
Alex Kracov: It's such a compelling pitch to restaurant owners. Because probably, most of them don't have custom fonts or don't care about design. They just want to focus on making good food and making their customers happy. This is all sort of unnecessary evil. I also love how you integrate so smoothly with DoorDash and Uber Eats while also giving them the ability to have their own ordering system and can be profitable on that. Because I always thought how much those systems must eat into restaurants' margins.
Kyle Norton: Yeah, they basically make no money on those orders. Restaurants, takeout and delivery restaurants, in general, are making less money today than they were five years ago because they're giving a good chunk of that marginally to the apps.
Alex Kracov: I'm curious how you think about, I guess, the top of funnel at Owner. Are you doing cold calling? Are you going door-to-door reaching out to folks? Then maybe a second part of that question is like, does geography come into play? Do you think about launching cities or different networks of restaurants? Or, is it all just digital, so it doesn't matter?
Kyle Norton: We're all digital. Lots of our competitors have feet on the street, and they knock on doors. There's an advantage to that. We have invested tremendously in our data infrastructure. Our ability to understand the highest fit, highest revenue potential restaurants across the nation, is way more valuable than the potential conversion rate improvements you'd get by actually being face to face. We're a fully digital sales org. Yeah, sometimes we'll have reps go in-person. If somebody really wants to meet us, that's fine. But why we're able to win, on a per rep basis, my reps close probably 3x the revenue on a per rep basis than a bunch of our competitors. Because we've relentlessly reduced low value work, bad data, and really just rooted out inefficiency in our system. That can be better done remotely. You're not spending 20 minutes in a car driving to somewhere, and then they don't show up. That's obviously not a great experience. We've really leaned into the fully digital model and a fully optimized, automated go-to-market approach. Because, again, there's tradeoffs. You get better conversion rates in-person. But then, you don't have the advantages of all of this digital infrastructure. We've really made that work for us.
Alex Kracov: I'm curious how you thought about building out the sales team over time at Owner? What does the sales culture look like at Owner? Maybe a part of that, I would like to know, are you in-person? Are you remote? How do you sort of think about building the team?
Kyle Norton: Yeah, we're fully remote. And as many other companies are pulling back into the office, return to office three days a week, we're very committed to a remote environment. It gives us a lot of scale. I can hire talent anywhere. It gives our employees a lot more flexibility to integrate their personal lives and their work lives in a way that's meaningful for them, that I think is very attractive. I think as more and more companies pull people back into the office, we become an even more attractive destination because we're still remote. And so you have to be mindful that you're hiring people with a very high sense of drive and an internal sense of drive. We just want to hire people with great discipline, great drive, and passion so that they don't need an office to stay focused and work hard. That I think is really important and will be a differentiator for us in the future. And if that's you, hit me up, if you're listening.
In terms of culture, I have a lot of opinions on culture. So I'll try to stay succinct here. But I think culture is actually less important than values and employee experience. Culture is a thing that gets thrown around. It's like, is it fun? It's like it here. It's like a shorthand for like is it fun to be at that company? That's why people are like, oh, culture is better in-person. Yeah, because it is more fun probably to be in-person. You get to pal around. There's like ping pong tables, and you can catch up over lunch. That is more fun. But I think what is important for me is, what actually produces business results? Well, that is high engagement, productivity, high employee retention. What you need for those things is not actually a fun environment. Yeah, you sacrifice personal relationships being remote. It's harder to build friendships if you're just on a screen. I fully admit that. You'll never really be able to replace that remote versus in-person. But if you go back to the research I really liked, which is this Gallup research called the Q12, the things that are most highly tied to employee engagement, an engagement leading to productivity and high retention rates, are all things we can readily deliver in our own environment.
Do people trust their manager and the leadership in the business? Do they feel attached to the vision, and do they care about that mission? Are they equipped with the tools they need to succeed? Are they getting continuous growth and development? Do they feel like they have career opportunities? There's sort of a list of 12 things. Only one of them, one of the criteria, I have a best friend at work. Everything else, you can deliver just as well remotely as you can in-person. Other than best friend at work, I will readily give that one to the in-person crowd. And so we just go hard at all of those things. We try to deliver it in a world class manner - development roadmaps for every reps, tons of training and coaching, lots of internal promotions. We're really committed to promoting from within, so people have that career progression opportunity for them. I'm hyper transparent. The same monthly update that I write to my executive team as to my assessment of the business, I publish that entire thing to my sales team, to the whole company. Then I do an AMA where people can ask me any single question they want. I don't sugarcoat anything. Those are the types of things that build engagement, remote or in-person, that I think people don't do enough of.
Is that culture? Not really. I think it's more employee experience and values. And so we did an employee net promoter score recently. It was like 87 on my team. People will tell you that it's impossible. It's impossible in a remote, but it's not. You just have to do the work. It's hard work. It's hard work to deliver that stuff. You have to be disciplined and write tons of documentation. But it works for us, and I think it'll continue to be a competitive advantage.
Alex Kracov: I'd love to end today's conversation talking a little bit about your own personal journey. Being a sales leader at a startup is tough. You just have that constant weight of a number on your head. How do you think about when prioritizing your own mental health as the company grows? But also, you keep getting better. You keep scaling yourself and keeping up with that company growth curve. It's a really interesting balance. I deal it with a lot myself. I'm curious how you deal with it.
Kyle Norton: Yeah, it's a great question. It's something we talked about a lot. On the mental health side of things, it's just about being disciplined in doing the stuff that we all know we should do. Are you working out every day? Are you eating pretty healthy? Is your sleep hygiene good? Are you reading and engaging your mind in other things outside of work? Are you taking the time to check in with yourself and ask yourself what you need? It's like, hey, I'm not going to lift weights today because I'm really wrecked from the week. It's like, okay. I'm going to do something else. So I think it's just that commitment.
Being in an environment where that's commonplace, I think, is really important. Everybody through the leadership team has that same priority. We talked about it a lot. The health and fitness channel is one of the most popular ones at the company. We talked about it at all hands constantly. I talked about it constantly with my team. So I think it's just about doing the things that we know we should do. You know if you drink, you're going to feel like shit. But how many people have two drinks every single night? Then you stay up too late, and you got your phone in your face until midnight. Then you're tired the next day. It's just discipline to do what we know we should do. That for me is the way that I am able to keep this pace. Because it is definitely a very fast pace for sure.
Startups, in general, and then Owner is sort of even at another gear, I would say. Speed is one of our core values. In terms of tradeoffs when I interview people, I'm like, hey, look. There's all these great things about Owner. They're going to seem exciting, but this is a performance culture. It's not a real work-life balance culture. You got to be ready to commit to it. You got to be ready to put career first. And if that's not you, cool. No big deal. Owner is just not your destination. You won't like it. Again, transparency. Then your second question was on, how do I personally-
Alex Kracov: Yeah, how do you stay up with the company growth curve?
Kyle Norton: Yeah, it's a commitment to learning. I read every day. Podcasts are a big part of it. When you reached out, I started getting into your pod. I'm like, oh, there's great stuff here learning about company building and just hearing those stories. So whether it's yours or 20VC - I've spent a lot of time listening to Lenny's Podcast which is a product management pod. But for me, as a sales leader, trying to be more well-rounded as an executive has been probably my best investment over the last two years. In terms of being a more well-rounded leader, I read a lot about product management because it's so applicable to building sales teams - just the systems thinking and the problem solving of it, and being a great partner to product as well. Those are the things I do on the daily.
And yeah, Toby says this a lot at Shopify. He's like, if the company grows 100% year over year, just to qualify for the job you currently have, you need to be 100% better next year. It's like if you want to get promoted, you probably have to be 200% better. That really sets the stakes for how much you're investing yourself. Network helps a lot. Pavilion has been big for me in that way. Having like-minded people that I can talk to and go meet for dinner. So again, it's just discipline to be committed to it. I think most people know what they should do. But finding the discipline to do it is the hard thing. So go read Atomic Habits by James Clear. That'll give you most of the answer key that I've lived by.
Alex Kracov: Well, thank you so much for the conversation today, Kyle. If people want to go work at Owner, if people have questions for you, where is the best place for them to find you?
Kyle Norton: LinkedIn. Yeah, hit me up on LinkedIn. It's just Kyle Norton. I'll come right up. Shoot me a DM. Tell me you heard me here, and I'm open to talk.
Alex Kracov: Awesome. Thank you.
Kyle Norton joined League — a health insurance tech startup — as VP of Sales in 2016.
In 2019, he joined Shopify as Head of Revenue for their retail division before being promoted to Director of Revenue & Merchant Success for Canada.
Today, he’s the CRO at Owner — an all-in-one marketing platform for restaurants.
Kyle Norton has led sales teams at two unicorn companies — League and Shopify.
While leading sales at League, he grew revenue to $20 million and scaled their sales team to 40 reps.
3 years later, he joined Shopify as Head of Revenue for their retail division to help roll out their point-of-sale products.
In today's episode, Kyle joins Alex to discuss:
Alex Kracov: I'd love to start today's conversation with your time at League, a health insurance startup. You joined league as a VP of Sales, and the company had just raised a Series A. What made you join League?
Kyle Norton: So it was an unorthodox Series A because there was no SaaS revenue yet, and the company was going through a huge pivot. But they were able to raise $25 million basically on the back of the founder. It was a third-time founder. He had sold his first two companies for hundreds of millions of dollars. And in Canada, that was very much a rarity. And so that's largely what I was drawn towards. I've always had a passion for health, frustrations about our healthcare landscape. The opportunity to work with a proven multi-time founder was really attractive, because I have never been in a true startup before. So it was really about the learning opportunity.
Alex Kracov: What was the company like when you joined? You mentioned there's this transition from, I guess, a non-subscription revenue. What was the state of the sales team? Can you paint a picture?
Kyle Norton: Yeah, so there was no real sales team. There was a few people doing some selling and some CS but for our like Uber for massages-type motion. They were trying to sell to big employers to get them to basically book services through our app. But we were transitioning to being a full healthcare provider for employers, an insurtech. So I was building the sales motion from scratch.
Originally, we were going to have three motions field, an inside motion that I was building and then a partner motion. The other two motions didn't really take. And so, basically, what I had built as the inside motion became the only thing that we did. So it was just me. I hired a small handful of reps, a manager from my network. We were just going at it with this brand-new messaging, brand new product, that sort of know we didn't have any customers on. We're just trying to get the first real deals, which is a weird thing. Because you find that product-market fit when you're a five-person company on a pre-seed round. We were trying to do it as a 30-person company. And so the pacing wasn't pretty different.
Alex Kracov: Yeah, it gets way harder to move when you have a much bigger team. More people you got to explain things too. It can't be as nimble. I'd love to go a level deeper there. How did you go about evolving that sales pitch in the process, even though you're a little bit more of a mature company? Was there founder-led sales that you were sort of building off of? How did that kind of work?
Kyle Norton: Yeah, so there was a lot of friends of the founder. We called them FOMs - friends of Mike. The sales team was doing all the pitching. We had Mike in some of our really big deals. But for the most part, we were just out there trying to make it happen. He would do sort of board engagements, or he would go over the top to the other founder. Because we were focused on selling into mid-market technology companies at first because they would be more forward-thinking about health care.
And so the iteration was really rapid. We were recreating decks basically on a weekly basis ourselves. We had one AE who's awesome in Photoshop and PowerPoint at the time. So we were just on our own iterating like, oh, we said this. We tried it this way. That got not the right response, so then we would redraft slides every week and then try to go out the next week and say something a little different. It took us a while to get to the right messaging that unified what the buyer cared about and what we could actually do in our vision. But it was very much a challenge our model where we were trying to get people to do something really different. So finding the way that we could communicate that message, while also not scaring folks off, was the tricky balance.
Alex Kracov: Over the three years I think you're at League, you grew revenue to $20 million plus and scaled the sales team to, I think, around 40 reps. Was there a moment where it started to feel like things were working, or were you always just sort of pushing a ball up the hill, and it was hard? How did you sort of feel about it?
Kyle Norton: Yeah, I always joke with the folks that I worked with in that era like, no, I never felt like it was getting easier. One of the interesting things about raising that amount of money and having those expectations is, you just have to grow so fast to keep up with the expectation of that financing. That as we started to get a pretty decent fit in particular markets, okay, we've got some good mid-market references. We're starting to build a name for ourselves there. Then it was like, alright. The company target goes up 3x next year. So we couldn't possibly do enough of those deals. So now we have to do only enterprise.
It was the amount of money raised and the expectations ratcheting up so quickly that really drove us to need to chase up market. Ultimately, that wasn't really the right decision. It was a significant struggle for us to win deals in markets where we had no references. We're pitching at 5,000-person company, and our most referenceable customer is 400 people. It was really, really difficult, and every deal was brute force. Every deal, you were having executives go over the top and pulling levers at their board level. We were multithreading all over the place and every deal had to be run picture perfect throughout. So you are losing. It never really felt like it was getting easier. They've since evolved away from that employer product and sell a more insurance platform product. So we never really got product-market fit in a true sense.
Alex Kracov: It's so interesting, the relationship between financing and capital raise and your go-to-market strategy and the expectations there. It sounds like you're forced to just do a bunch of inorganic things away from product-market fit to go chase those big goals. And yeah, I don't know. It's a thing that I think about a lot as we build Dock, to keep our valuation in check so we have reasonable goals. Because I think companies grow at a really - there's a natural growth rate to a company into an expanding market. And if you try and force it too much, it doesn't always work. Sometimes, it works. But I don't know. It's a tricky balance.
Kyle Norton: Yeah, especially true in disruptive technologies where you're trying to convince the market to do something different. So we were really trying to get employers to think about how they delivered healthcare and insurance to their employees in a very different way. The market just needs to mature. People need a little bit of time. I think one of the product-market fit challenges was being early. And so this problem of raising too much money wasn't really a thing in 2016. That didn't happen. It happened in 2019, 2020 where, as a founder, sometimes you'd have to say, actually, we're going to raise a more reasonable round. That dynamic, I don't think existed pre-2018. But we found ourselves there. And it was a tremendous lesson for me to learn. I share this lesson a lot with founders who I advise. Because it can be painful for sure. It makes you make short-term decisions that are not productive long term.
Alex Kracov: And so after League, you joined Shopify as the Head of Revenue for Retail. What made you make this move, from a Series B startup to an established public company?
Kyle Norton: I never thought I would go to a big company. Like many of us thought, the only real company building is in startups. That's the real stuff. Big companies are slow, and it's easy. Why would you want to go do that? Actually, a friend of mine, Jake Dunlop, I reached out to him just for some advice on it. He gave me a little bit of a come-to-Jesus talk. He was like, hey. He's like, you and me, startup guys, we assume that that's the only thing that is out there. But going to a big company, you learn a completely different set of skills and pattern recognition and mental models. He's like, you should think about getting that type of exposure. It was a blend of both. I got to go to the biggest, most successful tech company in Canada, which was exciting. But also, I get to build a new thing, like a new go-to-market motion for the point-of-sale product. So it was the best of both worlds. I loved it. I loved my three years there. I learned a tremendous amount and very different things than I learned in a startup. So I strongly encourage people to think outside the box if you consider yourself a startup person.
Alex Kracov: And so you mentioned when you joined, Shopify was rolling out this point of sales product to retail vendors, and you were put in charge of selling that solution. So kind of like a startup within a big company, if you will. Can you talk about the point of sales product, and how you approached sales? I mean, were you competing against Square and things in people's actual offices?
Kyle Norton: Yeah, so Square, LightSpeed, Vend. Yeah, the product that you're checking out with when you're at a clothing store, for example. And so the product was fairly well-established downmarket. There was $70 million in revenue in this business, so it wasn't nothing. But we were really just piloting a farther upmarket, human-led go-to-market motion on top of the self-serve motion that already existed. And so we grew the team from 5 people to 70 and changed in 18 months. Really moved the needle on the growth rate for that business and had a blast. It was a really exciting opportunity. I largely joined that team because the guy who ran it, Ian Black, I thought I could learn a lot from. He's a former senior Uber guy, super smart dude and was clearly going to do something exciting with that business. The product was great, and it was the opportunity to go build. So I had no regrets about it. I loved my time there.
Alex Kracov: What did sales actually look like? Are you selling into just existing Shopify customers who already have a Shopify website? Do you knock on doors? Do you do cold calling? How do you sort of approach it?
Kyle Norton: Yeah, it was a lot of expanding into the current Shopify base. We had a bunch of data to give us a likelihood that that e-commerce customer had a brick-and-mortar location, using a bunch of the Google API data and other stuff to take a best guess. That was the first nine months. Then COVID hit. All of a sudden, every business in the country needed to have an online motion even if they weren't all ready. And so the business ended up shifting from probably 80% expanding current customers with point of sale to almost 50-50 current customers expanding to new customers wanting to get set up online and then us saying, hey, if you're a brick and mortar, your brick and mortar is going to be closed. Move the whole business over now, so you have one system of record, one platform. Then when you're ready to open up again, you have a better place to deliver an omnichannel experience to your customers and grow faster. The motion changed a lot in COVID. We had to rebuild all the messaging and retrain folks. That was a pretty wild time.
Alex Kracov: I want to get into COVID a little bit more in a second here. But staying on the pitch, why were customers buying this? I assume it's the tie in to the website and the Shopify platform. Is this omnichannel? Was that the pitch? How were you able to go against Square, for example, or whoever the competition was?
Kyle Norton: Yeah, you're right on it. The point of sale feature to feature was either behind or just at parity. But the fact that the point of sale was attached to this ecosystem, the best e-commerce product, all this other tooling, and you could unify both the operations of the business so it's easier to operate if you're running Shopify across the business versus having something integrated or unintegrated, that was a piece of it. Also, it unlocked so many multi-channel marketing opportunities. Being able to have one customer record so that you can understand buying patterns. You could market to people who buy online to drive them in store. You can remarket to people who come in store because now you're capturing their data at checkout, and then get them to buy online. And so a lot of the data showed that if you can have somebody purchase online and offline, their stickiness was tremendously elevated. And so that was the pitch. Make more money. Simplify your business, and also be future-proofed. Shopify had shipped features and developed it at such a pace above and beyond everything else that you're saying, like, look, you know that this market is changing. You know that the customer is changing. So pick the partner that is going to be ahead of the curve. That was another big part of the positioning.
Largely, to tie League and Shopify together, we would use what I call a point of view positioning. And so this helps you really quickly let a customer opt in or opt out and qualify them upfront, and then build a lot of trust by saying like, hey, look. We're not the perfect product if you care more about inventory management and analytics and reporting. Our reporting is not as good as Lightspeed. And so if that's the most important thing for you, it's probably not us. But if you believe that in order to win in the next couple of years, you need to be able to service people online and offline, and they need a great online experience, then Shopify is sort of your only choice. Then that would let customers really quickly say like, yes, that's what I believe. So I should evaluate it. We did the same thing at League. If you believe X and Y about healthcare and what's wrong with it, then we should talk. It's a great way to build massive trust upfront and also just get the wrong people out of your funnel fast.
Alex Kracov: I love that point of view positioning because you're trying to lead them into the future. It's like anybody who's innovative and thinking about the future feel like they have to say yes to that point of view, right? As a retailer, you'd be all thinking.
Kyle Norton: Yeah, you'd be surprise. We would joke at League. If we could run a LinkedIn search algorithm to just find all the people that were wearing tech fleece hoodies and disqualify anybody who's wearing a blouse or a tie in their LinkedIn profile, that's how we should prospect. It was a little bit of a joke, but there's a lot of truth to it. Because we would pitch to somebody who has a very old school view of HR. It's risk management. It's legal. It's sort of like parenting your employees versus a more forward-thinking HR leader who understands, hey, healthcare is important for people. And if we can deliver this type of experience, they can be better healthcare consumers. It'll drive down costs. Some people just couldn't compute what we wanted to do. That was okay. The key was how to qualify them out as fast as possible. Point of view positioning was a great tool to do that.
Alex Kracov: Yeah, as I was researching for this interview, I was even surprised that Shopify even has a sales team. Shopify has such an amazing self-serve product-led growth business. Can you explain a little bit how is sales organized at Shopify? Because I know after you did the point of solution stuff, you ended up leading go-to-market for Canada. What does the sales look like at Shopify more broadly?
Kyle Norton: You're opening up Pandora's box with that question because it's changed so many times. There was a plus sales team selling the upmarket product. To customers with a million in GMV and above, there was a more sophisticated product. And so they had a sales team. That organization was probably 4 to 600 people before I started, but we didn't crossover at any point on the org chart. We were totally separate product lines. I was building something separate.
Then after the end of 2021, no, the end of 2020, we brought all of those teams together, regionalized. Every region sold all products. It was basically a train wreck. Not the right org design, bunch of weird decisions made. And so we sort of floundered for 12 to 18 months and tried to unwind that reorg incrementally. Because we over regionalized. We had duplicates of roles everywhere, really poor collaboration. And so that was a big challenge. And so we unwound a lot of that. A new CRO just joined. This guy, Bobby Morrison, I think his name is, from Intuit, he's whipped the place into shape. So now there's a lot more central specialization, a services model. They've brought back the retail team. My team got disbanded, which crushed me at the time. It was really sad to see. Now it's back as a thing. So what's old is new again. It's ebbed and flowed a lot. But it seems like in the last couple quarters since Bobby has got his people in there and he's making decisions, it seems like it's on an exciting pace, which is exciting for me because I'm a big Shopify fan. I'm super, super excited to hear that it's really clipping now.
Alex Kracov: It's an amazing company. Toby is just such an incredible, aspirational leader I look up to so much. But yeah, it's so interesting to hear org redesigned, stuff. Yeah, I could totally see how there's a lot of duplicative roles and how the GM model probably sounds good in theory. But in practice, it's like, okay. Now I'm hiring two of everything, and no one has actually specialized at anything. Yeah, it's interesting balance.
Kyle Norton: It sounded cool and it sounded like - I actually never liked it on paper. I wrote an eight-page document arguing against it. That didn't go anywhere. On paper, I got what they were thinking. But then in reality, it didn't totally make sense. Then the guy who was behind it left the business four months after it happened, so we were all left doing cleanup duty. Lesson learned. Again, it's frustrating at the time. But lots of interesting lessons in terms of great organizational design and how you can build high-functioning businesses. Yeah, but it was wild.
Alex Kracov: I'm curious how does Shopify sales teams sort of play off of that strong product-led motion. Are there triggers that you have, or it's like, okay, time for the sales team to reach out to this customer? Or, are you reaching out to net new people who have never even built in Shopify before? What's the balance there?
Kyle Norton: For a company of that size, we were actually a lot less sophisticated than you would think in terms of the use of data for go-to-market. On the product side, very high sophistication. That growth organization is probably one of the best in the world. Luc Levesque, who runs it and really piloted it, he's a badass. But we never really got that same level of sophistication in go-to-market. And so you did a lot through the tools that you did have access to, but a lot of that happened at the team level. The advantage was, you had a lot of customers that were growing quickly on Shopify's core products, and we had great data on those customers to try to upgrade them. Then on the sales side, everybody knew the best targets in their market. They're on our competitors. They are the brands that people know about. And so the prospect data was a little messy. They've just relaunched their whole Salesforce instance. I think that's getting better, but that wasn't our forte. RevOps wasn't our forte until, I think, recently.
Alex Kracov: Yeah, I think companies with amazing product-market fit, a lot of the times, the internal operations, you can get away with it for a lot longer than you think. I know Stripe had a similar situation. I've talked to people there. But yeah, I mean, when you have a great product-market fit, it covers up a lot of stuff.
Kyle Norton: Yeah, and you just have so much inbound volume. There's so much inbound volume, and the outbound conversion rates are so strong. Because it's Shopify. People are like yeah, I'll take a meeting. Yeah, tell me what's going on. What are you guys building? There was a genuine curiosity from customers to hear our point of view and what's going on, especially product-wise. So, yeah, that definitely leads to not needing to be crazy buttoned up. But that was a tremendous opportunity. I think now that the company is building a lot of go-to-market strength and a lot of go-to-market sophistication, that business will accelerate in a significant way. Because there is so much opportunity, so much data, so as the brand and power is so great. Their product is just unequivocally better than basically anything else out there for most pure DSC use cases. So I'm bullish.
Alex Kracov: You mentioned Shopify was uniquely impacted by COVID. First, there was all the uncertainty around small businesses and shipping. But then, Shopify experienced insane growth during the pandemic years. What was that experience like for you on the ground there, and how did that change how you approach coaching reps?
Kyle Norton: Yeah, it was just a blur, especially because I was in this point-of-sale group nine months into my role when it all happened. The entire team was under four months of tenure. And so we were on the fly changing stuff almost every day. We thought our business was going to just be eviscerated. We'd said, everybody, we're going to guarantee your full comp. We're going to pause the variable compensation plan. We're just going to pay you your full OTE. You're well taken care of. That was a very Shopify approach to things - taking care of people and doing the right thing.
But then, a couple days later, a couple weeks later, all of a sudden, we got the most insane inbound volume as all of these people were trying to figure out how are they going to survive as a brick-and-mortar business. We were the default choice. So we had to quickly pivot into a mode of, how do we just deal with this volume of inbound? How do we now pitch this new customer type that wants to move their whole business over to us? We were changing messaging and checking in on people a lot because people were just so busy. The Zooms of the world just fielding mass volume.
I think the thing that we did well there as a leadership team is trying to make decisions from the viewpoint of the customer. It's like, what does the customer really need from us right now? How do we deliver that at scale even if resources are relatively limited? That was a very Shopify set of values. It's like, deliver massive customer value is priority number one. Make money by doing that. And never forget, don't confuse one and two. And so the customer centricity and how you're enabled at Shopify to actually make customer-centric decisions was, I think, the best thing that we could have done at that point. Every decision we made, it's like, okay, well, how does this affect customers? Does this let us serve more people? Does this let us get people, help people faster? And so every week, we were making changes and updates and changing qualification criteria to help more people. It was a good lesson in customer centricity. Massive numbers of those businesses are still in Shopify today and thriving.
Alex Kracov: Switching gears a little bit. Now you're working at a startup called Owner as the SVP of Sales and Partnerships. What made you leave Shopify? Maybe a better question is, what about Owner that made you want to go do another early-stage startup?
Kyle Norton: I said I would never go back to early stage after League. I was like, that's too crazy. I just had my second kid. I was really happy at Shopify. I had no intention of leaving. But one of the venture capital funds I'm involved in, GTM Fund, invested in Owner. And so, through that process, I met the founder, Adam. We ended up being on calls every week. There was just a magic there. I was doing some advisory stuff. At some point, Adam was like, hey, I know you're not really looking around but - he's like, would you consider exploring, joining us full time? I'm like, oh, I don't know. The time is not right. Maybe in September timeframe. As I started to learn more about the business and spent more time with Adam, I just came to the realization. I was like, my philosophy on investing is like it's all about the founder. Yeah, you want a big market. But Uber was black cars for rich people, and now it's just logistics. PayPal was payments for eBay, and now it's this massive fin tech platform. Okay. So market can change. If we think, market, product, team are the three variables. Market can change. Product can definitely change. Good products can catch up, and it can get better. Great products can lose a step. But really, what's the thing that determines success? It's just like, is that founder truly elite?
As I've learned more about early stage, it's not just about being a great founder. I think great maybe gets you to a Series B or something. But to really go do something special, you need to be truly different, truly world class. That's what I saw in Adam. It was sort of FOMO more than anything. I was like, I can fast forward this movie three or five years. I can see myself being on LinkedIn seeing some insane announcement from this company and being like, wow. I could have been there. I missed out even though I knew that this guy had some magic. Adam and Dean, the two co-founders, I was just I'm insanely impressed with. And so I just sort of felt like I had to do it. I couldn't miss this opportunity. Because they come around so infrequently. I have never met a guy like him, ever in all of my investing advisory or just being involved with startups. I have never really been around two co-founders that have the discipline and drive and learning motor. The two of them were just insane learning machines. So I jumped in. Even though the timing couldn't be worse. My son was three months old. Personally, it was a very challenging six months with two young kids. But I'm very glad I made that decision because it's been an awesome ride, and I'm very optimistic about where we're going.
Alex Kracov: Yeah, Adam Guild is super impressive. I mean, I had a 30-minute, an hour call with him talking about marketing. Everything you just said resonated with me. I was like, oh, wow. This guy is an amazing learning machine and just very unique. He is also very young, which is interesting. What is maybe his first real company he's ever worked at? What has it been like working with Adam to build out sales at Owner? What has that transition been like from founder-led sales to sales-led sales?
Kyle Norton: I'll separate those two questions. Yeah, the learning machine thing was what caught my attention. I remember it so clearly. We were talking on a call about messaging. I was like, oh, I really liked this book Made to Stick. It's got some good frameworks to just simplify things for customers to better understand. Then 18 hours later, he texts me. He's like, hey, I read that book. One, it was impressive that he just read this book I mentioned offhand in 18 hours. Then two, he just started asking me these questions. Not clarifying questions. They were questions I would expect to get from a seasoned go-to-market operator that's been doing this forever. It's like, Jesus Christ. He just read this book, and he has clearly synthesized this information so massively. And so I think that is his superpower.
Your other question was about, as a first-time founder, that ability to learn incredibly rapidly means that we don't need to learn as many of those painful for some founder lessons as you otherwise would. Because that super learning, combined with an intellectual humility, avoids a lot of those mistakes. He has a good network. He reads voraciously. And if it's go-to-market stuff, when I share my opinion, he's really open and interested in it and is genuinely inquisitive and curious. He's like, oh, how do you think about that? What about this? And even if we have a disagreement and we're talking it through, if my logic is sound, he's like, okay. Great. That sounds like the right decision. Let's do it that way. The humility and lack of ego to not need to be right every single time or not need to do it my way is way more rare than it should be. That allows him to operate way beyond any first-time founder that I've been around personally.
Alex Kracov: Can you explain a little bit about what is Owner and maybe how has the sales pitch evolved, if it has, from when you started to what it is today?
Kyle Norton: Yeah, so the core problem we solve - I'll answer this from the restaurant's perspective first. The core problem we solve is, over the last five to seven years, the guest has changed a lot. Now digital ordering is not just a trend but it's very much an expectation. Uber Eats, obviously, the third-party marketplaces, in general, were gaining a lot of prominence. Then COVID sent it from clear trend to basically an overnight absolute. My parents can use Uber Eats. And if my parents are using Uber Eats, it's a wrap. They're not exactly the world's best technologists.
That means, for restaurant owners, they need to be able to deliver not only good food and service but a great digital experience. They need to be able to be found online and have a good website. That's definitely not in the core competencies of 98% of restaurant owners. They got into that business because they love food. They didn't get into the restaurant business to be digital marketers. And so they oftentimes are trying to keep up with the customer by cobbling together a Wix website and use ChowNow for ordering. Then they'll use like a text provider and MailChimp for emails. They put it all together. They don't do an awesome job. Then they basically get nowhere. Their customers are still buying from Uber Eats, where they're paying a 30% commission. It just leaves them insanely frustrated and actually losing money.
And so, Owner, out of the box, solves that whole problem. And so we provide them a website, an online ordering experience, so people can actually order directly from them. We API back into delivery networks, so they can still get the delivery drivers even if they don't want to deliver in-house. Then email and text message marketing tools, loyalty program. We custom-branded app for every customer. It's all wired up with AI, so AI will assist them if they want to write a custom email or create campaigns. We've got a bunch of cool AI stuff that we're releasing over the next little while. The outcome is, they make way more money. Oftentimes, we're doubling our customer's direct delivery business in 90 days, which is super cool. They do way less of the stuff they don't want to do. They now let us do all of the heavy lifting on digital marketing, and their business is way more profitable. It's cool to support small business in this way. If you go read our G2 page, for example, everybody says the same story. It's like, "Man, I was stressed. I hated trying to do this on my own, and now I'm making all this money." That's super fulfilling.
Alex Kracov: Restaurants are a super tough market. I mean, I started my career selling sales at Yelp and cold called restaurants. I feel like they've been burned by so many vendors in the past. They've been thrown - I mean, you mentioned a few. Wix, ChowNow, and then you got DoorDash, Uber Eats. How were you able to stand out and build trust as you work with these restaurants? Because as you said, they're not amazing technologists. I feel like they're skeptical as you reach out. It's like, hey, we're going to solve all your problems, and we're going to save your money.
Kyle Norton: They've definitely heard all of that before, and they don't believe a word you're saying. Yeah, 100%. They have every right to be skeptical because they've gotten sold a bad bill of goods a lot. There's two things. One is the sales experience, and two is sort of how we contract and interact with the customer. I'll start with the contracting because it's a little straightforward. We don't do long-term contracts. So every customer signs up with us month to month. If they don't like it, they leave. We will give them all of their customer data that can one click export. We'll help them revert back to their old website. So we're really lowering the stakes of making a mistake for the customer, and showing them it's okay. We're going to put our money where our mouth is. If we don't give you a great result, we're going to make it super easy to walk away. And so you have to have some trust that we can deliver. Or else, we'd get crushed as a business if we made it easy to walk away. Even in the early days, we had a money back guarantee on top of that. We pulled that away because we don't need it. It reduced customer commitment. But we act with a lot of transparency and customer centricity. We make it easy to do business with an easy to walk away.
But then, on the positioning side, going back to that point of view positioning, I have a radically transparent sales style. And so I want my reps to tell customers what's good and what's not good about Owner. And so the tradeoff that we architect for a prospect was like, hey, look. No product is perfect. That doesn't exist. Every product has advantages and disadvantages. The disadvantage, the tradeoff of using Owner, is you're going to get a lot less choice and customization. Your website is going to be our core template. We're going to build the email journeys for you. You don't really get to choose the order and how those things look like. We're going to change the style and the comp copy. But you're going to have to fit into a box with Owner because we know that these are highly optimized templates and patterns that are going to work and deliver results, deliver revenue for you. But in exchange for giving up flexibility and choice, you're going to make way more money. You're going to do way less work, and your life is going to be better.
And so if you care more about design and aesthetic, and you've got a brand guide that you had some marketing partner do, and that's what you care about the most, don't use us. Choose BentoBox. It'll cost you way more, but you can make it look super pretty and all this stuff. But if you just want results, if you just want to make money, then we're the choice. That level of transparency, again, just lets the right people opt in and be like, "That's exactly what I want. I don't want to do any of this crap." Okay. Cool. Your trust goes way up, and your buyer can opt in faster and vice versa. The people, it's like, oh, wait. So I can't do my custom fonts? No, you absolutely can't do your custom fonts. Okay. Cool. Then it's not a fit. Great. Cool. No big deal.
Alex Kracov: It's such a compelling pitch to restaurant owners. Because probably, most of them don't have custom fonts or don't care about design. They just want to focus on making good food and making their customers happy. This is all sort of unnecessary evil. I also love how you integrate so smoothly with DoorDash and Uber Eats while also giving them the ability to have their own ordering system and can be profitable on that. Because I always thought how much those systems must eat into restaurants' margins.
Kyle Norton: Yeah, they basically make no money on those orders. Restaurants, takeout and delivery restaurants, in general, are making less money today than they were five years ago because they're giving a good chunk of that marginally to the apps.
Alex Kracov: I'm curious how you think about, I guess, the top of funnel at Owner. Are you doing cold calling? Are you going door-to-door reaching out to folks? Then maybe a second part of that question is like, does geography come into play? Do you think about launching cities or different networks of restaurants? Or, is it all just digital, so it doesn't matter?
Kyle Norton: We're all digital. Lots of our competitors have feet on the street, and they knock on doors. There's an advantage to that. We have invested tremendously in our data infrastructure. Our ability to understand the highest fit, highest revenue potential restaurants across the nation, is way more valuable than the potential conversion rate improvements you'd get by actually being face to face. We're a fully digital sales org. Yeah, sometimes we'll have reps go in-person. If somebody really wants to meet us, that's fine. But why we're able to win, on a per rep basis, my reps close probably 3x the revenue on a per rep basis than a bunch of our competitors. Because we've relentlessly reduced low value work, bad data, and really just rooted out inefficiency in our system. That can be better done remotely. You're not spending 20 minutes in a car driving to somewhere, and then they don't show up. That's obviously not a great experience. We've really leaned into the fully digital model and a fully optimized, automated go-to-market approach. Because, again, there's tradeoffs. You get better conversion rates in-person. But then, you don't have the advantages of all of this digital infrastructure. We've really made that work for us.
Alex Kracov: I'm curious how you thought about building out the sales team over time at Owner? What does the sales culture look like at Owner? Maybe a part of that, I would like to know, are you in-person? Are you remote? How do you sort of think about building the team?
Kyle Norton: Yeah, we're fully remote. And as many other companies are pulling back into the office, return to office three days a week, we're very committed to a remote environment. It gives us a lot of scale. I can hire talent anywhere. It gives our employees a lot more flexibility to integrate their personal lives and their work lives in a way that's meaningful for them, that I think is very attractive. I think as more and more companies pull people back into the office, we become an even more attractive destination because we're still remote. And so you have to be mindful that you're hiring people with a very high sense of drive and an internal sense of drive. We just want to hire people with great discipline, great drive, and passion so that they don't need an office to stay focused and work hard. That I think is really important and will be a differentiator for us in the future. And if that's you, hit me up, if you're listening.
In terms of culture, I have a lot of opinions on culture. So I'll try to stay succinct here. But I think culture is actually less important than values and employee experience. Culture is a thing that gets thrown around. It's like, is it fun? It's like it here. It's like a shorthand for like is it fun to be at that company? That's why people are like, oh, culture is better in-person. Yeah, because it is more fun probably to be in-person. You get to pal around. There's like ping pong tables, and you can catch up over lunch. That is more fun. But I think what is important for me is, what actually produces business results? Well, that is high engagement, productivity, high employee retention. What you need for those things is not actually a fun environment. Yeah, you sacrifice personal relationships being remote. It's harder to build friendships if you're just on a screen. I fully admit that. You'll never really be able to replace that remote versus in-person. But if you go back to the research I really liked, which is this Gallup research called the Q12, the things that are most highly tied to employee engagement, an engagement leading to productivity and high retention rates, are all things we can readily deliver in our own environment.
Do people trust their manager and the leadership in the business? Do they feel attached to the vision, and do they care about that mission? Are they equipped with the tools they need to succeed? Are they getting continuous growth and development? Do they feel like they have career opportunities? There's sort of a list of 12 things. Only one of them, one of the criteria, I have a best friend at work. Everything else, you can deliver just as well remotely as you can in-person. Other than best friend at work, I will readily give that one to the in-person crowd. And so we just go hard at all of those things. We try to deliver it in a world class manner - development roadmaps for every reps, tons of training and coaching, lots of internal promotions. We're really committed to promoting from within, so people have that career progression opportunity for them. I'm hyper transparent. The same monthly update that I write to my executive team as to my assessment of the business, I publish that entire thing to my sales team, to the whole company. Then I do an AMA where people can ask me any single question they want. I don't sugarcoat anything. Those are the types of things that build engagement, remote or in-person, that I think people don't do enough of.
Is that culture? Not really. I think it's more employee experience and values. And so we did an employee net promoter score recently. It was like 87 on my team. People will tell you that it's impossible. It's impossible in a remote, but it's not. You just have to do the work. It's hard work. It's hard work to deliver that stuff. You have to be disciplined and write tons of documentation. But it works for us, and I think it'll continue to be a competitive advantage.
Alex Kracov: I'd love to end today's conversation talking a little bit about your own personal journey. Being a sales leader at a startup is tough. You just have that constant weight of a number on your head. How do you think about when prioritizing your own mental health as the company grows? But also, you keep getting better. You keep scaling yourself and keeping up with that company growth curve. It's a really interesting balance. I deal it with a lot myself. I'm curious how you deal with it.
Kyle Norton: Yeah, it's a great question. It's something we talked about a lot. On the mental health side of things, it's just about being disciplined in doing the stuff that we all know we should do. Are you working out every day? Are you eating pretty healthy? Is your sleep hygiene good? Are you reading and engaging your mind in other things outside of work? Are you taking the time to check in with yourself and ask yourself what you need? It's like, hey, I'm not going to lift weights today because I'm really wrecked from the week. It's like, okay. I'm going to do something else. So I think it's just that commitment.
Being in an environment where that's commonplace, I think, is really important. Everybody through the leadership team has that same priority. We talked about it a lot. The health and fitness channel is one of the most popular ones at the company. We talked about it at all hands constantly. I talked about it constantly with my team. So I think it's just about doing the things that we know we should do. You know if you drink, you're going to feel like shit. But how many people have two drinks every single night? Then you stay up too late, and you got your phone in your face until midnight. Then you're tired the next day. It's just discipline to do what we know we should do. That for me is the way that I am able to keep this pace. Because it is definitely a very fast pace for sure.
Startups, in general, and then Owner is sort of even at another gear, I would say. Speed is one of our core values. In terms of tradeoffs when I interview people, I'm like, hey, look. There's all these great things about Owner. They're going to seem exciting, but this is a performance culture. It's not a real work-life balance culture. You got to be ready to commit to it. You got to be ready to put career first. And if that's not you, cool. No big deal. Owner is just not your destination. You won't like it. Again, transparency. Then your second question was on, how do I personally-
Alex Kracov: Yeah, how do you stay up with the company growth curve?
Kyle Norton: Yeah, it's a commitment to learning. I read every day. Podcasts are a big part of it. When you reached out, I started getting into your pod. I'm like, oh, there's great stuff here learning about company building and just hearing those stories. So whether it's yours or 20VC - I've spent a lot of time listening to Lenny's Podcast which is a product management pod. But for me, as a sales leader, trying to be more well-rounded as an executive has been probably my best investment over the last two years. In terms of being a more well-rounded leader, I read a lot about product management because it's so applicable to building sales teams - just the systems thinking and the problem solving of it, and being a great partner to product as well. Those are the things I do on the daily.
And yeah, Toby says this a lot at Shopify. He's like, if the company grows 100% year over year, just to qualify for the job you currently have, you need to be 100% better next year. It's like if you want to get promoted, you probably have to be 200% better. That really sets the stakes for how much you're investing yourself. Network helps a lot. Pavilion has been big for me in that way. Having like-minded people that I can talk to and go meet for dinner. So again, it's just discipline to be committed to it. I think most people know what they should do. But finding the discipline to do it is the hard thing. So go read Atomic Habits by James Clear. That'll give you most of the answer key that I've lived by.
Alex Kracov: Well, thank you so much for the conversation today, Kyle. If people want to go work at Owner, if people have questions for you, where is the best place for them to find you?
Kyle Norton: LinkedIn. Yeah, hit me up on LinkedIn. It's just Kyle Norton. I'll come right up. Shoot me a DM. Tell me you heard me here, and I'm open to talk.
Alex Kracov: Awesome. Thank you.
