20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

24:25There's a lot of companies that are stagnant and then there's a lot of BDRs who are quite good that don't necessarily have that path to where they're at. Can I be a dick? Where do the best BDRs come from? Where do not good BDRs come from? You can find good BDRs and freeware. I like Jason's advice. Go to a company that's not number one in their category. Who's the number one BDR at a second and third place company? Because that's hard. And if you have a great product and you bring that person into your environment, they'll do really, really well. We've hired a bunch of people, you know, that company where we've hired nine people from, that's a mediocre product in a very competitive market.

25:02And those people are well trained salespeople that come into an environment and they rip. because our products great. And so now they have good sales craft, they've got the grit, and now you marry that with a number one product in its category, and people will take off. Okay, and so I just want to go back. So we have this data enrichment layer, which is super smart. And so when we look at the economics, when it's 9K, I go back to Chris Dagnan, actually, we both know. And he said, basically, you can only have six to eight calls a week. When you think about that, for you, obviously, yours is a much higher volume game.

25:35Yeah. How does yours differ? So in Chris's context, there will be so much pre -call research and post -call work and coordination and quarterbacking. Like I've sold enterprise before. So I think that makes sense. We aim to have roughly four demos booked per AE per day with three held. We know that there's going to be some meeting. Three demos per day. Every day. Yeah. Wow. So they're going to do We tend to have calls today. Three demos a day plus probably two to four follow -up calls from previous pipeline. We also close a ton of calls on the first demo. We're doing a bunch of analysis right now to figure out exactly what that marginal point is.

26:16How many net new lead calls do you think your team have a week? Hundreds, for sure. Yeah, because 26 account executives, they're probably... But I each of them, do they do 20 a week each? 10 to 20 probably 12 to 18 I bet is like, but if they have 12 to 18 that would mean everything who wanted to be conversed with demo every You said they need to have three demos a day. Yeah, so the in the BDRs are booking those for them. I got you Okay, got you okay, so the BDRs, but then how many BDRs do we have? 35 isht and so 35 book three net new each or call it to a call to to each yeah, wow inbound is different than outbound So those it's two net new for outbound is one and a half to two inbound is a lot more than that inbound They'll they could be doing five to ten because it's it's a higher intent should a ease be responsible for pipeline generation in SMB.

27:10I don't think so in general I think relying on account executives to prospect is probably a losing proposition Why would you pay a 250k rep money to make cold calls when you could potentially have an 80k BDR? do that work for you if they're good at it. I think account executives, especially mid -market enterprise, have to do some prospecting, but it's not bangin' the phones. No offense, BDOs, if they're paid like shit, which respectfully they are, aren't you wishers gonna get bad people? No offense, and again, they're the front line of your company. How do you think about effective BDO hire and given they are more junior?

27:47They are the future leaders of our industry and our company. we hire super high caliber people that have a ton of potential. And so you gotta do a lot of training. But this is the point of their career that they're at. 80K is awesome for them. And they have a path to 100 and 150 within two years. You're 22 years old, that's awesome. I don't necessarily think it's like a bad comp. How do you think about target setting with them? Because I always think that incentives can be gamified. So you can do like demos, but sure, I could just fudge the qualification process and get you a load of donut shops that are shit and going out of business Not going to help.

28:26So our BDRs only get paid on clothes one business. Alignment. Our account executives only get paid when their customers go live. We are month to month contracts. So We want to make sure that our account executives are doing high quality handoff setting good Setting good expectations are closing high quality customers and so again, they are highly incentivized to make sure that those customers are good so that they go live. Right, and they're called... A Mac call does not include transmission revenue. It does. It includes an estimate. So we have these two machine learning models. One is EGPV, so it's an estimated gross payments volume.

29:02So we scoop in a bunch of information from them online and we can make an estimate of how much they'll actually do on our platform. And so that goes into their comp, so that we're rewarding them for closing the highest quality deals because there is a spread. Wow, does that ever get you in trouble? I want to mean by that, is say a chain goes out of business and you pay comp on estimated volume, and actually they didn't hit it, they wait off it. Ah, not happening. You'll win some, you'll lose some. It all comes out in the wash. We feel really good about our economics and we know that when we changed comp to include EGBV, which means they are gonna be more focused on the higher value customers for the business, Our estimated MRR on a per -deal basis went up pretty significantly.

29:46What is a good ratio? Say you pay an AE, I'm just making it up, like 200k. Is it 5 to 1? Is it in terms of like revenue? What is good? It depends on company stage. Early you probably won't get that, more mature for sure. We're way above that. Because we have instrumented so much, the product's really good, a bunch of us inbound. So what do you are? a good account executive, like our inbound account executives close 250K ARR every month. So it's a little different because we're not basically close a client a day. Yeah, or more, more in a lot of cases. Wow efficiency. This is the thing. So when people talk about, well, you know, one of the things that surprises people is on the upbound side, we have two BDRs for every account executive.

30:33Oh, that makes no sense in SMB. Well, it does if on a per BDR basis, the LTV CAC is really strong and then you're closing a high percentage of those deals. Again, this goes back to first principles. As a revenue leader, do you really understand your P &L inside out and backwards? And do you understand the inputs and outputs of your unit economics? What, the most revenue leaders miss on the standup P &L? They don't even understand it. They don't know where to start. They think it's the domain of finance. And finance gives them a head count number and they say, you have 17 reps and you have to do this and they say, okay, where they get the number and they just complain about it.

31:10But they don't really understand sell by sell. The ARR model that we have, I understand it sell by sell. Every single input, because I own demand, and growth as well. And so I have to connect all of these things to make sure that not only this month, but six months out, we have the right trajectory for all of these things to ladder up to the number. What's our AQL forecast from growth? What is the confidence interval that we're getting to this number by this date? Okay, what are the redundancies we have in place? And I'm always trying to layer in more than I actually anticipate will need because one channel will falter something weird will happen.

31:48But then on an input by input basis, you have to have a high degree of proficiency or else you get surprised. This is what ends up happening to a lot of first time, PPs of sales is they go into a quarter, they don't have enough pipeline and they go, oh, we have to generate like an extra four million in pipe and close it at a 25%, but our deal cycles 120 days, you're cooked. There's no way to recover. You made that mistake six months ago. And so unless you really understand the model and are able to think both about today and delivering what's happening right now and be thinking six and 12 months into the future, you really struggle.

32:27What channel has outperformed expectations and what do you learn from that? Organic probably. What do you think you did well to inspire organic do so well? I did nothing. That was never start with that. It was me. It's the takeaway, but yes. Yeah, this was a founder insight. This is Adam having an incredibly deep understanding of the customer in the market. and way before it made economic sense, he was all in organic. Adam just has such an intuitive understanding of our customer base and he was like, we're all in on YouTube, we are gonna be the central hub for restaurant marketing. No one owns this position online.

33:06And so we hired people that manage the YouTube experience for the biggest creators in the entire world. And we were paying millions of dollars for this organic strategy when it was driving like a handful of leads every single month. That's a really bold leader because you have to basically be comfortable losing money without guarantee that the rewards will come. Yeah, long payoff time horizon, but compounding. So now we have more social media followers than our public company rivals already. And we're only in the early innings of getting great at this. And people will come inbound and be like, I've watched 12 hours of Adam's YouTube, like here's my credit card.

33:46And that happens fairly frequently. And we weave his content into our onboarding journey into customer marketing. This channel seemed like a crazy bet at the time. And I knew better than to second guess this one. Like Adam just has an ability to see ahead and make a bet. And when he does that, he's almost always right. Do you not think this is when marketing completely blends with sales? Because actually so many, you have outbound sure, but outbound is made far more successful when you outbound to someone who already watches your videos. 100%. This is something that a lot of folks get wrong is they squabble over attribution.

34:25They're like, oh, this is sales generated, this is marketing generated, and you end up at these local maximas. And we have a sort of a strange org structure where our VP of marketing, who owns brand and PMM and customer marketing roles directly into Adam, I own growth and demand gen, you would think like, oh, that's a little squirrely and it works awesome. And everybody collaborates and it's a really productive structure. And my growth leader doesn't worry about like organic attribution, neither does the VP of marketing. They understand that a ton of organic is actually driven by the paid marketing halo.

34:57So we don't worry about it. What channel has sucked when you thought it would be good? We just tried CTV and didn't have a ton of success with the connected TV. Connected TV. So running pre -roll ads on Amazon Prime or the like set top boxes. What do you think happened there? Really what happened is we've got too many other things that are successfully taking off and we just diverted resources. Was it expensive? Wasn't that bad? That's the cost of experimenting. We're going to spend hundreds of thousands of dollars on these channels to try to figure it out. And we know that not all of them will take off immediately.

35:30And that's totally okay. You know, you got to think in bets, Andy Duke. The world is probabilistic and some of these will work and some of these will won't. Some of these won't. And we're going to triple down on the winners. And what do you sell cycles? A lot of one call closes, But average sales cycles under a week. Under a week. How is that the case? I mean that with the most respectful. That is extraordinary. It's a compelling product that helps and it's a burning platform for people. Like we are helping them make money which is very important so folks are willing to move on it. But something else we do that I think helps a ton.

36:03The style of selling that I teach is radically transparent selling. At the beginning of every demo, what we lead with is both the strengths and weaknesses of the product. So like one of the first things I'll say to a customer when I'm a call is, so I feature dump number one, which everybody tells you not to do, but I actually think people talk in such weird abstractions that customers don't understand. I'll be like, okay, we do five things. Website, online ordering, email text, message, marketing, custom branded app, listing management, all rolled into one. So that's like the product. But here's what you need to know about what's different than us and our competitors.

36:37We are going to give you way less flexibility and customization. If that's your main priority, owners probably not a good fit. But in exchange for sacrificing this flexibility, you're going to get way better results. And why that is is because we have thousands and thousands of these restaurant customers and we're constantly doing experiments in AB tests and the things that work, we're going to roll out to every single customer. And we're not even going to ask you some of the time. And you have to be comfortable with that. But in being comfortable with that you now get an army of experts legitimately the best restaurant marketers in the world and some of the best restaurant marketing Technologists are working constantly on your behalf to do one thing and one thing only which is make you money You make more money do way less work But if you've got a custom font that you really love or you want videos everywhere and a spinning pizza sign at the top of the website You have like really strong brand opinions then it's not really gonna work And so what happens is the wrong customers opt out immediately.

37:32And so you're not wasting a bunch of time in sales cycles. And the thing that drags on your total sales cycles is actually time to lose more often than it is time to win. But because we lead with that transparency up front, what you notice is that you're starting that conversation with massive trust with the restaurant. This is like the four star review thing from Tocca Pony. Like people don't trust brands that have only five stars. They actually have a higher trust in four stars. I'm leading with strengths and weaknesses, so now people are trusting the rest of what we say. And we're really honest.

38:02When you're selling to SMB, a mum and pop, how many won't customisation? Some for sure. Really? Yeah. And we have some larger brands, 10, 20, 30 location brands now, many who have grown up on us. You know, we've helped them be so successful that they've franchised, they've opened a whole ton of locations. Do you have a constant internal battle of how far into enterprise you go. It's surprisingly easy because we're committed to the mission and we're committed to this product philosophy. We're not against working with a 30 location brand, but we are against working with a brand that wants high degrees of customization.

38:41More of those brands are gonna want more flexibility and choice and are just gonna say, oh, actually this isn't the right fit. But we closed a 33 location chain the other day and they came to us and they're like, yeah, I don't want to deal with all this stuff. I just want somebody else to figure it out for me. Okay, great. Here. Let's see. But if you look at Olo, if we're blunt, why are they not a good business where you are? They're playing a different game. They're playing a very different game. I'm sorry. I'm naive. How so? Well, they're way up market. They're trying to win enterprise brands and they're trying to play the customization and flexibility in the headless game in tons of cost pressure there from these major franchises.

39:19I don't know that it's a bad business. but they're just doing something completely different. We don't cross over with them hardly at all. When you look at how you run your internal processes today, there's real velocity slash action to your cell cycles that's very fast compared to others. How do you do pipeline generation meetings? How do you do deal with you? So what are the staple meetings in a cell? So we don't do pipeline review. Okay. Why? We don't do deal review because you can just see it on a dashboard. It's all programmatic. At the beginning of the month, I can basically tell you where we're going to land because I look at what is coming in top of funnel from marketing.

39:57What do we project from the BDR team? And we can drive to that number. So it's really about butts and seats ramp, the average attainment. You can mathematically just figure out where that's going to be. So oftentimes, I can tell you that from dashboards. I don't need to do a bottoms up. What's your confidence level on this deal, like that makes no sense in SMB. And then, or price obviously it does, and you're gonna do a weekly scrutiny on every deal and stress testing it. But for us, I can understand everything I need about the business, but basically from the sales source. What was your ramp time on new A's?

40:30So we've interestingly extended this recently. Why? We wanted A's to start in the role better trained. We used to put people on the phones on day five, and now it's like day 11 or 12 because again, the deal doesn't matter unless it launches. And so if you are a new rep and you're saying a bunch of stuff that's like sort of not accurate, then you get into launch and they're like, wait, I didn't know about this and this and this. Then the trust is completely broken and oftentimes people will pull up again because we're contracting month to month. Does that matter though? And what I mean by that is your pool of net new leads is so large compared to insurance, SaaS business where they sell to enterprise, where there's like, don't fuck up a lead here, dude.

41:15Like, you can't afford to. Do you not bluntly have such a big universe? Like, you can get them on the cool earlier and not fuck it up. They're still an opportunity cost because we've paid money to generate that opportunity that another more seasoned rep could have closed, both inbound and outbound. That's true. And so we're also mindful of the reputational risk as well. and we want people to be really successful and competent. If you throw them in way too early, then sometimes it actually stunts their growth. Do you do shadowing? Like, will sales eat as drawing calls for the first, cool second, cool third, cool?

41:50Oh, yeah, big time. Like, cool to me about that, because again, I never run a sales team. That's why these shows are successful, because I asked the questions that everyone who has no idea what they're doing, ask too. How do you do that? When do you hand off? The reps will go through the training and they do a bunch of the sales simulation, then mock calls, they get certified, they get certified on the craft, and then they do an operator certification, which is like, you know what do you sales force and all the other stuff. And then their first calls, the managers are on all of them, basically.

42:18And you'll give the rep more and more rope as they show competence. So maybe at the beginning, all the rep can do is open the call, ask if you discover questions, do a little bit of the demo before they get that deer and headlights look, and then the manager can jump in and take it over. So we see a lot of like manager closed deals in that first couple of weeks. In the nicest way, how sophisticated are the clients? And what I mean by that is if you're a mum and pop shop with maybe a couple of Chinese stores or a couple of Indian restaurants, are you really like jumping on to like sales, demo calls from a plush office being like, oh, thank you, Carl and Jessica.

42:55Lovely to see you. Are you like, hey, why are you bothering me? Yeah. Fuck off. A lot of people are joining the Google will meet from their phone, they're in the back office, smoking a dart is not an uncommon experience on our demos for sure. And so, like, yeah, these are salt of the earth, mom and pop business owners. We'll meet the customer wherever we need to meet. How important is it to go in person? We don't do any in person. You don't do any in person. Alabbaal, why? The economics don't make sense. We're so efficient running the sales cycle digitally. I'm not being rude if you go to like a highly dense metropolitan area.

43:32Is there not like 50 mom and pop shops in the square? So we are highly targeted. I mentioned that we have these two ML models, one that tells us the size of that potential restaurant, so like how much revenue they'll do, and we have this thing called an E -Win score. And so that's our estimated win rate. Wow, is it fast, Danny? What size restaurant is interesting? So we don't want little tiny restaurants that are just like scraping by and have no customer traction because we charge a premium. We charge 500 bucks a month. And you don't want Sean. Yeah, obviously. Okay. Exactly. So they're doing like 500 K to 5 million.

44:08Yeah. And so we know that there's certain GPV bands where churn starts to tick up. So we say, okay, like this is our minimum for this segment. And then we have this estimated win rate. So you could knock on 50 doors. Don't laugh. It's the likelihood of closure greater in different cuisine types. So like if your GPV is under 300 grand for Indian But under 700 grand for Italian. Is it different in that way? I don't know. We haven't run that analysis I didn't be fascinated you know all the Italians they close under a million. Yeah Chinese that better on 500k Yeah, we look at all sorts of stuff churn by cuisine type churn by size churn by the quality of their setup like everything in our business is instrumented so that we can understand it in a lot of depth.

44:53Gosh, you don't want to spend a ton of resources if the challenge is high. Mm -hmm. Okay. And so going back to your question about it in person, a rep on our team that is getting, you know, three to four demos a day and closing one or two of those and then being able to chase down all of their follow -ups, it's really hard to compete with the efficiency of that model, knocking on doors. Some of those doors are relevant, some of those doors don't meet our scoring model. Most of the time the owner's not there. You're now like feet on the street. It's just a ton of time. And our competitors who run that model, we're anywhere between like three and four times more productive on a per -re basis of those companies.

45:31I think it really shines through for me from this conversation is like a velocity engine of a sales machine. Do you know what I mean? Which is like very systematized and very scientific. It's fascinating. So we have that with different stages of sales come different challenges. You guys scaled really fast. How fast did you scale 10 min in revenue? What were you at when you joined? Two and a half. You were at like 40 today? Yeah, fuck it, miss. Under three years. Yeah, we're actually growing faster today than we were. Three years to 40 min in. Yeah, two and a half to that. And we're actually growing faster today.

46:10And so I'm very optimistic about what this year will bring. Does customer acquisition get cheaper over time because you have brand, you have word of mouth, you have a humming sales and marketing team? What does they get more expensive as you expand beyond your core ICP? It depends. So it depends on how big the market is. I think many markets you hit a saturation point and you've closed the low hanging fruit with the early adopters and you see sales and marketing costs rise. It's falling pretty rapidly for us. We're getting more and more efficient as we grow. But we've also made tremendous investments up front.

46:46Revops, enablement, data and biz ops. These are for anybody else looking at it would think like these teams are way overweight for the size of team in the ARR we are at today. But we've built these systems and foundations that are allowing us to get increasingly efficient. and now as we bring in more and more reps and spend more and more in demand, then that flywheel is pretty tough to stop. What is the biggest thing that Revolpes is done to make a humming and efficient machine do you think? A few things. One is trying to automate and obby skate all of the low value stuff. We use momentum that looks at the transcript of every single sales call, and it fills in the Salesforce fields for the rep.

47:30It fills in their opportunity to record it updates the account, the person, it says whether or not the event was run or not, all of that stuff that could take a wrap a whole bunch of time to manually fill out. That's all done for them. We try to simplify the business process as much as we can for the reps and then tooling. We're really insistent on trying to bring in tools that make the team more and more effective. Both pre and post sales. I think sometimes the pre sales gets all of the investment and post sales doesn't, but a company that I know you know is Pavlov and they're, we were their first customer.

48:06Yeah, Mark and I worked together very closely at Shopify. I didn't know that. I did it with them last night. You know, we let that run. I do. Oh, well, fantastic. I should have known that. I love him. He's so good. They're an awesome team. I'm very bullish. And so we're using the tool like Pavlov to post sale, incentivize the customer to take actions that we know lead to higher GPV, higher retention. And again, that's now an automated flow where they go through these campaigns of incentives. They do the right things, not just for us, but for them as businesses. How do you think about that? How do you do that successfully?

48:44Because, you know, as you said, there's disaster revenue, which is great, but also transaction revenue, so meaningful, meaningful part of it for you. And so when you think about really ensuring customer success, what have been your biggest lessons in how to do that well? Again, it goes back to data and infrastructure. One of the things that the Bizops team did is build a scoring model for customer configuration quality. It's called the growth potential score. They did a big regression analysis and we know exactly what things in the product, if they're set up well or not well, drive GPV, drive growth.

49:18And if a customer is making money, they're making us money and they're much, much higher retention. So we get paid back multiple times there. So we built this GP score, the Bizops team does. And so we now know what a really high quality configuration looks like. That information is available to the launch specialist. So as they're setting up, they can see their GP score, they can see all the GP score. So what's a launch specialist? An onboarding rep. Okay. And so what do they do? They set the customer up. So sales closes it, they pass it to the launch specialist and they get access to their domain, their Google Business profile, they build the website, figure out their menu and photos, the integrations, they're doing all of that work.

49:58Wow. It's quite cheap, isn't it? Like 500 bucks a month, you actually think about it. Six grand a year and with you, everything you get feels pretty good. It's pretty good deal. Yeah. And a bunch of these customers end up making... I'm thinking like the margins are not great then. Because if you got like a launch specialist doing all of that shit making menus Domains make your sights up to quality for them. They're happy with color schemes and the fonts and They do a lot of launches every month on a per person basis. Any launch is Over 20 per person plus their Latin American based They comped on a on a launch they are Yeah, and going back to this growth potential score thing.

50:40So the launch specialist knows what they need to fix in the configuration so that that person is as successful as possible. What are their photos? What's the density and quality of those photos? What's the story we tell? Do we have connection to their Google's business profile? If we do all the business listings work. Is the SEO done properly? All that stuff is again delivered programmatically. You said they're Latin based. Talk to me about that. Are they internal resources? Yes. Okay, why Latin based? Just like a pricing arbitrage? Yeah, and on a per dollar basis, we get incredible talent. There's an exciting opportunity in Latin America to not treat it as this like BPO at an arms length type thing.

51:24We've made them part of our team. They're how? That's pretty hot, gee. Anything worth doing is hard to do. We just like did the work to go source. And so we've got a really good recruiting team. We like posted the roles and did all the normal stuff, but they were going outbounding into these markets, it's looking at where are the hubs of potential talent. So big American tech companies that probably are getting good talent, let's go source there. And once we found the patterns and they interviewed hundreds and hundreds of people and found a system to basically identify good folks. How many do you have in Latin?

51:5870 people probably. Wow, how basic company now? Approaching 250. Fuck. What breaks with scale? Everything. Yeah. I think one of the things that I am most hyper paranoid of is the quality of leadership breaking because I think once, you know, if there's a long period of time where tons of people reported directly into me, I seized it and then managers did. And so I was really close, like within arms reach of every person in the oracle now there's multiple layers between me and any I see. Is that good? You hear about founder mode and the importance of being close to customers? Is that good to be having multiple layers between you and an IC who's then going to speak to a customer?

52:42Well, I still get on demos almost every week. You do. Yeah. At the end of a month, I'll be on demos almost every single day running calls with reps jumping in if they need help closing. I love it. It's fun for me, but also it's very important for me to keep my craft sharp and to know what's happening on the front lines and I got involved in all the biggest deals last month. I was like, hey, anything above 10 locations, like get me in there that's what I'm going to prioritize. And I ran a bunch of these calls and then wraps her like, oh, like you said this and this, like I'm going to do that. Can you send me?

53:10Can you send me how you're thinking about it? We like quickly sketched out. So because I've had these new ideas, the best way to figure out if they work is doing myself. So I'm pretty intentional about staying connected. My BDR manager RIPPS dials himself, the AE director runs demo still. The new manager who started is going to be like an AE basically for his first 30 days and get like very, very close to the customer. What bit of the machine keeps you up at night? Talent acquisition. Yeah, because it's really hard. It's really... As specific as possible, I'm so sorry, but is it BDR acquisition?

53:42Is it launch specialist acquisition? It's the speed at which the number is growing in every single role. Because at some point, my content engine, like basically me, cranking LinkedIn, will only get us so far. And so we need new channels. and I'm trying to make sure that we have these new sourcing channels lit up Before we hit a point where it's like oh man We we're supposed to have seven people starting we only have three and then you're starting to take action and it's sort of too late I just did a university tour. I went and spoke at all the best business schools in and around the GTA as Part of like a new way to source candidates and we have seven new SDR starting next month just from this and then another four in July And so again, like it comes back to this theme of how can you hit today, but also think about tomorrow?

54:32We're both fans of Jason Lamkin. Jason always just tells me, listen, young people just don't want to work today. Like they used to. They just don't want to work. Does that chime true with your perspective? I think in general, there may be some truth to it, but there's still plenty of people out there with the grit and work ethic and tenacity for us to build a world -class team with highly motivated people. I have not personally found that with my thoughts. Do you think reps are coinal prices? No, no, I think it's always a mixture of incentives. It's too binary to say like, oh, they're either money motivated or they're mission motivated.

55:07I think a lot of people are really excited about our mission because you get to help an SMB, a person that's like easy to feel good about helping. But yeah, everybody in sales wants to earn money. If I came to you and said, I didn't give a shit about the mission, just being honest, I care about making money and I'm gonna crush quota and I'm gonna be here night and day crushing quota. Makes me nervous. Does it? Yeah. Why? They'll just go to the next thing where they get offered more money. Is that not okay if I crush quota if he's two years? I might not even get two years out of them if that's the case.

55:38Especially because owner has so much brand equity now. This happens all the time where founders CS and they go, I just need to seed my team with people from that organization. Yeah, they're gonna try to overpay, but if that individual believes in the mission and we're doing the other parts of that engagement methodology. So I have this methodology called Cranps. So there's like five things I want to do to make sure people are highly engaged and retained. So community, so do people feel a sense of connection to the business and to the mission that we're supporting? Recognition is huge. I didn't invent any of this stuff.

56:15You can read any of the engagement research and get this stuff. Autonomy. So this is from Daniel Pink, Autonomy Mastery Purpose. Do they have a sense that they are empowered to go out and do their thing? Do they have an internal locus of control? Because there's this thing called the over justification effect. If you are glomming on to them constantly and getting people to do their job is just push, push, push, push, push, push, push, then you take away their internal locus of control and they actually will become less motivated. So I want to give them a sense of autonomy that they are in charge of their career and their business.

56:46So community recognition, autonomy, mastery, mastery is do they feel like they are on the path mastering the craft of sales that is deeply motivating for people. Do they have a sense of purpose? That's all about mission. So that's like 20 % of this methodology. And then the S is steps. So do they have a steps as career progression? Do they have a path to grow their career from BDR to AE, to senior AE, to manager? And so I'm very cognizant that we are equipping people to do that. And then giving them the opportunities. We promote a lot from within. Even though I could go higher, basically whoever I want, now from this market, we promote heavily from within because I think that's such an important engagement driver.

57:27You're scaling into a new phase of sales leadership for you. What are you nervous about as you scale yourself as a sales leader? That's a really good question. I'm a podcast. A good one at the hat. I go on dates and girls, that's a really good question. I'm like, I have had practice. I had an old boss used to say I pay it or be paranoid and I'm just sort of paranoid about everything. I'm paranoid about everything breaking. Our management team am I scaling them fast enough to keep up with the pace of the business? Are we going to have the recruitment engine? Are we going to be able to continue to source deals?

58:04I'm sort of scared of it all and that is like a really positive motivation. What did you do that you wish you hadn't done? We haven't had as much success hiring senior reps, like reps with a whole bunch of experience. We've actually had more success hiring people in like a two to four year experience range. Jason Lamkin would say they know how hard it is and they don't want to go back again. They're heads of sales or they've promoted up the hierarchy. And actually if you've done it once, you don't want to do it again. True or not true? I think it's more like we are highly, as you can tell by this podcast, I'm highly opinionated about how I want things done.

58:40And we're going to give you a lot of coaching and a lot of feedback and we want you executing on our system. Yeah, very systematized, like not much room if you want to bring in new flavor of sales respectfully. There's freedom within a framework. I want people to have some creative freedom, but it's got to be within a methodology. You know when your wife says, do you know, of course you can go out with the boys. It's your choice. That's kind of the same thing. Oh, maybe. I'm like, oh, I need to stay in. I'm just like, yeah. And so I think more senior reps come in and like, I know how to do this.

59:11I'm good. I'm gonna do it my way that's worked for me for a whole bunch of time. And oftentimes they can't outdo our system. Even though they have more experience and a more developed skill set, them executing their skills, but within this other framework is less good than a newer rep that says like, yeah, this sounds great, I'll do it your way. They tend to accelerate faster. And that's not all the time. Like two of our very best reps had a lot of restaurant tech experience beforehand. But in general, I think like as we've gotten to this point in the company, people that are earlier innings of their career and more malleable and open to ways of doing things and coachable, we're just like a hardcore coaching environment.

59:51You're going to get coached every single week. Every month you get a monthly report card that talks about what you did well and where there is of development. And then you develop your secrets, like what are we going to do for the next 30 days together to move the needle on whatever conversion rate. Some people just aren't about that anymore at this point of their career and we had somebody opt out in like three or five weeks just because she was a really senior seller and clearly was like, no, I'm not about this. So that's what you had done, you wish you hadn't done. What have you not done that you wish you had done?

1:00:21I wish I had been more insistent about hiring a head of apply AI. What? We're just hiring this role right now. I have been come absolutely obsessed with all things AI like as soon as Chatchy PT came out I have like a Clay table for my podcast prep that's connected to a tally intake Forms where the person fills it out then it updates the clay table and it runs these enrichments and creates questions for me and does all of this stuff Like I have this everywhere in my life. I should sound like a raw it on a Friday night. I I've actually remind me to reserve my calendar. Sorry, dude. I actually five coded an app on a Friday and I had a couple weeks ago, so you're not wrong.

1:01:05Stevie case. So I had her on my podcast. She was talking about her initiative. I was like, I want this. Like I need that for myself. And, you know, I mentioned the role and we're like, well, like let's come back to that. And I should have at that point being like, no, no, like let's get this role in today. And now I think we've just put up the JD online because I want somebody that is just like thinking and breathing all things AI across our entire business. I would like to be farther ahead than we are with AI even though people tell me that like we're so far ahead. I'm I respectfully why why do you need custom AI versus off shelf AI application could be off shelf.

1:01:44We're using a lot of off shelf stuff, but somebody has to think about okay, that entire ecosystem is this builder by. and how is it all getting weave together in a really cohesive manner? I'm pushing on my REBOPs team to all get really conversant with GTMAI and we're starting to get there, but I just want somebody dedicated to go absolutely all out on it. Wow. What does sales teams do today? There's no way they'll do in five years' time. Account research, lead prep, lead research, figuring out who to call. I think it's insane that companies do that today, that they have BDR's doing manual lead research.

1:02:21If you look at most BDR teams, like 30 to 50 % of their time is just flush down the toilet, with work that a data ops team should be doing for them. Does outbound become less valuable in a world of infinite supply? What I mean by that is I can just bluntly send 10 ,000 emails in a minute with AI outbound email systems. And we've got AI SDR tools. I mean, I'm laughing with the team, so because obviously I'm an investor for living too. I think we've seen 15 AISD hours in a week. That's just what we've seen in a week. You see these massive trends and ultimately that advantage gets competed away. Same thing with sales engagement.

1:03:00I was one of the first customers of sales loft cadence. At that time, you could just have every BDR sending 100 emails a day. The BDR team that I inherited at Vision Critical, five X to their per person output after my like seventh month there. And a lot of that was just nobody was using sales engagement tools. And so we loaded up all of these lists. And we were just blasting out fairly generic messaging straight from the old school predictable revenue playbook. God, our nose. Oh, yeah. Fuck me. That takes me back. But that playbook was incredible when it first broke. And then everybody started doing it and then it stopped working.

1:03:37And so there's this red queen's race where everybody has to move to the next thing and the next thing and the next thing. Yeah, I still think there's a tremendous advantage with some of this generative AI outbound. It will get competed away and a tip for all sales leaders that I think they should do is leverage podcasts to acquire customers and speaking to stakeholders. That's what I mean by that is we have an amazing company that sells to patent lawyers. Interviews of the lot partners at the largest patent law firms and talk about their challenges and how they think about the future. don't sell the company tool.

1:04:11And then after the show, they'll be like, so what are they gonna do? And you're like, oh sure, let me tell you for five minutes. You do one a week, you got 52 leads a year. I met a guy who generates 60 something percent of his company's funnel this way. They have five podcasts this company. And all they do is interview the biggest names in their industry. And that person almost always introduced them to the person they actually want to talk to. and then that person posted the episode on their podcast and I'm on owners the manual podcast and I'm so excited that all of the competitors are like oh my god what the fuck is that yeah it's a great strategy but not but it's so underutilized and it's actually underutilized because the cost of entry is still quite high versus posting on LinkedIn you have to get riverside you have to get a microphone you have to get the gas versus tweeting or blogging am I doing any of that shit?

1:05:04Still quite hard. But even that is nothing investment. What's a podcast like 200 and something bucks and? I have no idea, but not much. No, I completely agree with you. My entire home studio setup was like 2 grand. I completely agree with you, but people are lazy. They are, and it's still much harder than posting on LinkedIn. Yeah, you're out wrong. And my favorite thing about Secrets is you tell the world and people still don't listen. Do you know what I mean? People ask me this all the time. I'd be like, aren't you afraid you're like giving away all of the stuff that your company's doing? And I tell them it's like, one, I don't think anybody's really going to do it that well.

1:05:41This was something from Stevie. Like execution is the only moat. And I'll always execute, I'll execute these folks. Yeah. I'm 100 % confident in that. And the other piece is like, if you're a direct competitor of mine and you start using my tactics, I'm in your head. You know now that I'm better than you are. And you'll have to carry that with you, always knowing that you're one step behind and you're just trying to copy me. My mother actually, I walk with her every weekend in a marathon. And she always says, what the fuck, why are you telling everyone to do this and to do what you do? And I'm like, because I'm telling them that I'm making spaghetti bowl nays.

1:06:20I use analogies for her. And she's like, right. And I'm like, yeah, but there's two different types of people. One goes to Trader Joe's and Visible and there's Mix in the Pastor. The other makes the fresh pastor with the whole wheat that they got from the farmer's market. They do it the night before so it can aerate in the fridge. They then go to the farmer's market for the tomatoes. It's the how you do what you do. You could tell me to do the podcast like you do. But dude, if I didn't have the processes that you do, the clay tables, the research, the tone, the excitement, doesn't fucking matter if I do the podcast.

1:06:52It's how you do what you do. And again, this comes back to first principles reasoning. You know, people are going to hear what we do, and they can try to slap that onto their business. But what we do only works because of this entire ecosystem of what we do. Like, we run a highly structured system, and we invest in a certain way. Like, you need to follow my playbook. You need to do all of the things. You can't just be like, oh, we're going to do AI -lead enrichment. We'll just drop that in. Unless you have the enablement and adoption from the BDR team, so that they're not just like doing their own stuff on the side.

1:07:25Execution is the whole piece. Do you think it's valuable to have competitors in your head? Do you like to inspire teams with, A, we're beating X competitor? We don't that much. Yeah, we'll joke around about it, but it's not really our driving motivation. It is the mission. It's easy to feel good about helping a restaurant down the street, just survive and get by. And a lot of the motivation for the team is sharing these success stories. Like you see your customer in one of the channels that's grown like 3X and they're making like 6 grand more a month, which you know, it doesn't seem like a lot of money.

1:08:01But if you're a restaurant owner and you're a take home is like you're working 100 hours a week and net, net, net, net, you're only making 80 grand. And now there's an extra 40 grand in your pocket because we've helped you grow online, which is highly profitable. It's easy to be really excited about that. We do pay attention to some competitors, but we're running out of it. Which competitor did you most respite? I have a lot of respect for toast. Good product craft. Their GTM execution is really good. They operate in a pretty respectful way too. We don't find toast doing shenanigans to their customers.

1:08:33I think the competitors that I have complete disregard and disrespect for are the ones that treat their customers poorly. These are SMBs and you're trapping them into a contract. you're holding their domain hostage so they can't move over. You're lying to them about all of this stuff and trying to fear longer as they're trying to leave your company. That's pretty and excuseable, especially when I said mom and pop shops who are vulnerable and don't have the power. That makes me mad. I know that in the long run we will win because of that. You know, in the short term, I'm sure it's helped them hold onto some deals and stem some churn here and there, but none of those customers feel good about that relationship.

1:09:11And again, And I think one of the smart things that we do at owner and certainly a lesson I took from Toby is like Toby always talks about we're building a hundred year company. And one of the things that at owner we've done is like optimize for the long term. Like why don't we lock customers into your long contracts? We probably could. Well, we wanna earn your business every single month. Does that lead to some short term churn? Yeah, does it put tremendous pressure on us on product and execution to deliver an amazing customer outcome? Yeah, and I think long -term that compounds and becomes a durable advantage.

1:09:43Like, we, part ways really nicely with people. If you want to leave owner, we'll actually help you move on to your next thing. You want to revert your website. You need us to give you DNS records and stuff. We actually do more than we really need to make it easy for somebody to transition because I think that brand in the market compounds over time and is clearly something that builds steam for us. I want to move into a quick part. I can do it to you all day. You are advising a 23 year old. I'm your little brother, okay? And I'm 23 and I've got my first job in sales. I'm a rap. What do you advise me knowing all that you know now entering this workforce?

1:10:22Mm -hmm. Focus on the inputs and not the outputs. Focus on your work ethic, your rate of learning, your coachability, learn consistency every day, daily discipline. and know that the outcomes will eventually come. Got it. Love it. Reflect back on your time with owner. You can relive one of the days, which day do you choose to relive and why? That's a really good question. We had a pretty good one recently. On Wednesday, the end of April, we had to have a big surge to hit the number. And I was in the office in Toronto. There was a bunch of reps in the San Francisco office. They're all remote, but we had them go in to basically just like do this end of month surge, bring the vibes.

1:11:07I was in the office till like one in the morning with just like one rep left over and we closed the last deal at like 12, 15 AM Toronto time and the West Coast reps closed deals even even later than that. It was just a really cool moment because we knew it was an important month for the company and even at 1030 there was BDR still making calls to the West Coast to try to to get like last demos done, we were closing the very last deals. I just had a blast. We were collectively pushing for this number, even though almost every one of those reps is already at their number. They didn't really have to do it for themselves.

1:11:41And I think that is a special part of owners DNA. Yeah, we have people that are very individually motivated, but this like collective is pretty special. What have you changed your mind on most in the last 12 months? I think ChatGPT and OpenAI are unwaveringly the dominant leader for the next 10 years, and I think there'll be a $2 trillion company. I questioned that in the early days. Something that I changed my opinion on quite recently is O3 is potentially AGI. I wrote about this a bit on my newsletter. There was such a stark difference to the capabilities of O3 compared to everything before it.

1:12:16I mentioned how I wanted to hire this head of apply AI earlier. I started playing around with O3 and I updated a bunch of my like, Chatchy PT workflows to use O3 and I was just like, holy crap, this is so different. The memory, the reasoning, like the speed and being able to do research, and also deeply reason, it made me think that this roadmap is moving even faster than I anticipated. You can take Jason's side or Rory's side on who is right, is AI gonna bring mass unemployment in a way that we haven't seen before? I don't think so because of Kevin's paradox. You saw this argument as compute got cheap, well, all these foundation models going to be less valuable.

1:13:00It's no, it's cheaper now. Everybody's using way more compute. And so if the effectiveness of every salesperson and the effectiveness of all these individual contributors goes way up, are we going to want way, way more of those? I think yes, and I think AI is going to drive so much more company creation that there will be a consistent demand for these roles because the economics of the roles get better. There's more companies that need sales reps. I mean, I cannot read the future on this topic, but Jeff and Paradox may lead to high employment. How do you motivate sales teams when numbers are missed?

1:13:36It's about the actions you take before you miss the number. I think if you tie your identity to whether or not you hit the number, then when you miss the number, it's much more difficult to handle. but a thing that we talk a lot about at owner, it's about the inputs and the daily grind, and it's about the journey. A thing that I get quoted for us saying is, sales is a personal development exercise, disguised as a career. Sales being hard is a feature not a bug of this job. Failure is a feature not a bug of this job. And so if you can get people into this like more stoic mindset, that like the challenges are the journey.

1:14:16And failure is the journey. That's what helps us get better as people. That's what helps us grow and develop ourselves. Then when you inevitably have these down periods, you're prepared for them mentally. Like we've vaccinated people against those difficult times. Tell me, owner, 2035, 10 years out. Where is owner then? I think we'll be a generational public company. The only reason I left Shopify, because I loved my setup there. I still love Shopify. I think it's an amazing company. I think Toby is one of the greats. There was nothing making me want to leave shop. The only reason I joined owner is I think, Adam has the chance to be a generational CEO.

1:14:58I think he's got all of the DNA. This is a massive market, and this is a chance for me to hit a grand slam. It seems really arrogant, but I want to be one of the handful of people that have taken a company from early lead to IPO, you need an incredible team in market and all this stuff to be able to make that happen. And I thought owner was that bet. And I actually feel more bullish today on that than I did three years ago. Did I have loved this? I'm so appreciate you sending over your thoughts. So we obviously have our research. I'm very glad that I bluntly freestyle most of the time. It's so much nicer, but you've been amazing.

1:15:32So thank you so much. This was awesome. I really appreciate the invite. This was like a career bucket list thing for me and I've been a fan and a listener of yours forever so this was a blast. I mean that was such a special show to do. It makes such a difference being in person. We have so many incredible founders reach out and post shows like this and say how they change their organizations because of shows like this. Let me know what you think you can email me harry at 20vc .com. But before we leave you today, if you're ready to leave rigid payment terms behind, Camp Chase is here to change the game.

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