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

Kyle Norton is the Chief Revenue Officer at Owner.com, where he scaled revenue from $2M to $40M ARR in under 3 years while selling to one of the toughest markets: SMB restaurants. Before Owner, Kyle led sales at Shopify, where he helped architect one of the most operationally elite GTM orgs in SaaS. Agenda: 00:00 – From Shopify to $40M ARR at Owner.com 06:40 – Why Founders Who Skip Sales Get Burned 11:50 – 90% Inbound, Then 70% Outbound — And Why Neither Is Enough 17:40 – How to Use AI in Sales to Massively Increase Outbound 24:30 – BDRs Don’t Get Paid for Demos. Only Closed Revenue. 30:50 – The 3-Part Sales Scorecard That Replaced My Gut 36:20 – I Posted a Job on LinkedIn and Got 1,200 Applicants 42:15 – I Fired a Rep on Day 11. Here’s Why. 49:40 – We Don’t Do Pipeline Reviews. The Secret... 55:00 – The One Call Close Script That Wins in 99% of Cases 1:03:10 – Why YouTube Is Our Underrated Growth Weapon 1:14:30 – Sales Is a Personal Development Exercise Disguised as a Career 1:20:45 – The Night We Closed Until 1AM and Hit the Number

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  You are listening to 20 Sales with me, Harry Stebbings. Now, 20 Sales is the monthly show where we sit down with the best sales leaders to discuss how they start, scale and maintain incredible sales teams today. Now, I'm so excited to welcome an incredible guest in the form of Kyle Norton. Kyle is the Chief Revenue Officer at Owner.com, where he's scaled revenue from 2 million to 40 million in ARR in under three years while selling to one of the hardest markets, SMB restaurants. Before Owner, Kyle led sales at Shopify, where he helped architect one of the most operationally elite GTM orgs in SaaS. And Kyle is really known for turning sales orgs into machines. At Owner, he's systematized this incredible revenue engine

• 0:44Harry Stebbings?

  that we really unpacked today in this show. Get the notebooks out. It's a very granular tactical episode where Kyle was fantastic. But before we dive into the show today, if you're ready to leave rigid payment terms behind, CapChase is here to change the game. CapChase brings B2C buying convenience to B2B software and hardware purchases. CapChase offers your buyers the flexibility they demand on annual and multi-year contracts while you get paid upfront every time. This means faster closings, higher deal sizes and a streamlined process without the hassle of discounts or collections. Over 2,000 companies already use CapChase to accelerate their sales and secure predictable revenue.

• 1:24Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:53Harry Stebbings?

  Otter's trusted by over 25 million users, including Fortune 500 companies, to boost productivity and collaboration. So are you ready to take your meetings to the next level? Well, head over to get.owner.ai/20vc and grab a 30% discount. My word, they're so generous. When you subscribe to a business plan for your team, that's get.owner.ai/20vc. Let's make your meetings work for you. You have now arrived at your destination. Carl, it is such a joy, man. I literally was chatting to Jack Altman last night. I was chatting to Jason this morning. They said wonderful things. I'm not sure how much you paid them, but so appreciate you joining me today, man.

• 3:34Speaker 01

  Yeah, I'm stoked to be here, being a listener since the very, very beginning. So this is a ton of fun.

• 3:40Harry Stebbings?

  Dude, so glad we could do it in person. I would love to start though. I think we're shaped a lot by our experiences. And you were obviously at Shopify before. How did your time at Shopify impact how you think about effective selling today with Owner?

• 3:52Speaker 01

  So I actually think the lessons that I most deeply took from Shopify are on the product side. And you can't be taken seriously at Shopify without being well versed in the language of product. I oftentimes joke that the hierarchy is engineering is the top of the totem pole. Then it's design and product management. There's janitorial services here and then sales is like just below that. So if you want to be somebody whose opinions are listened to, like you have to know product and have to speak in that language. And so as soon as I got there, I started to get to work. I did like a reforged course.

• 4:24Harry Stebbings?

  Did you become a better sales leader through product knowledge?

• 4:27Speaker 01

  A thousand percent.

• 4:28Harry Stebbings?

  Wow.

• 4:29Speaker 01

  So much of building a great go to market organization is systems engineering. I'm sure we're going to talk about this a ton today. And product management in building product is that it's it's systems engineering. It's being able to get to first principles and root cause. And then reason up from there. That skill set has translated tremendously, like even the individual frameworks. From Teresa Torres, I use her opportunity solution tree, or like I take Marty Kagan's vision setting template. And so like I only discovered these things.

• 5:00Harry Stebbings?

  So what is an opportunity solution tree and how do you use it?

• 5:04Speaker 01

  It's a way to map from symptom to root cause. And I think one of the biggest challenges that revenue leaders have is we solve things at a surface level. And oftentimes we just like reason by analogy. We see a best practice on a podcast or something like that, and then we slap that into our business. And we don't ask ourselves the question, okay, win rates are low because of rep execution. So we'll go fix rep execution, but you don't go, why is rep execution not good? Well, is it a management thing or is it a training thing? It's a training thing. Well, why is there a training deficiency? Why, why, why, why, why? And you can sort of map from this opportunity solution tree from like symptoms all the way back to root cause. And oftentimes with this tree, you get back to the root cause.

• 5:48Speaker 01

  And then actually there's something else to fix there instead of all like, we just need to update the scripting. Well, you might get up to this top opportunity, this root cause, and then actually find, because you're trying to think of like, okay, what are the other ways? That I could solve this opportunity and it just forces you to more deeply ideate and solve problems more foundationally, I find.

• 6:08Harry Stebbings?

  I love that. I find a lot of the time we need frameworks. A lot of the time it's like we need clarity to understand the next step. I want to start, dude, on something you said to me before. You said revenue leaders spend way too little time here. And don't think about it strategically when it comes to recruiting and talent development. If we start at the beginning of the funnel, sourcing.

• 6:27Speaker 01

  Yeah.

• 6:28Harry Stebbings?

  What are your biggest lessons on what it? Takes to source amazing sales talent.

• 6:32Speaker 01

  So number one, I think revenue leaders need to see this as one of the most core components of their job. Oftentimes they look at this as the realm of TA and it's the talent team's job to bring them candidates. Let's post jobs, we'll put it on a bunch of boards and then we'll see what we get from there. And that's just totally backwards in my opinion. Revenue leaders, especially if you're trying to operate at a pretty dynamic scale. This needs to be something that you're spending a massive part of your day on or thinking very deeply and strategically about it. Because many of these bets have long, long time horizons on them. So like content. So I've been writing on LinkedIn for six, seven years. I've amassed a bit of a following. And so in the early days of owner, I could post a role, we would get 1,200 applications.

• 7:15Speaker 01

  We would get 60 to 100,000 impressions on every single job post I put up. And then that was picking from an incredible funnel of people who I'm basically sourcing myself.

• 7:27Harry Stebbings?

  Was the quality high?

• 7:28Speaker 01

  Yeah, yeah, for sure. Because these are all people that are one and two degrees connected to me. And then working referral networks really, really hard because everybody I know sees that. My whole network sees it and they know the quality of what I do. And if I'm putting my name on this new company, they're like, oh, that's probably a good opportunity. And sure enough, a former BDR of mine introduced me to his cousin. His cousin was our first BDR and he's like an absolute savage. This is a guy named Brayden. Then from that same company, now there's nine people that work at owner from that.

• 8:01Harry Stebbings?

  Wow, I bet they're thrilled with you.

• 8:04Harry Stebbings?

  When did you join owner in terms of sales team stage?

• 8:07Speaker 01

  There was a manager and four reps.

• 8:09Harry Stebbings?

  Management and four reps.

• 8:10Speaker 01

  Yeah, we parted ways with two of those reps fairly quickly. And then we've built to, I think, 60 folks in sales today.

• 8:17Harry Stebbings?

  Wow. Okay, let's go back to that. So Adam starts the sales process. Does the founder need to be the one to build that sales playbook?

• 8:25Speaker 01

  So not to get into semantics, but it really depends on what you mean by playbook.

• 8:28Harry Stebbings?

  Basically a framework for what customers want.

• 8:31Speaker 01

  Yeah.

• 8:31Harry Stebbings?

  Where they get it, how to message them and what a standard sales cycle looks like with a price average.

• 8:38Speaker 01

  If that's what we're calling a playbook, then yeah, I firmly believe so. I don't think you can outsource that to a new VP of Sales from the outside. I mean, I hear you talk about this all the time. I hear the range of opinions, but unless a founder can do that, I don't think that they're going to understand the customer in enough depth. This is a Toby thing. You know, he talks a lot about compressing the distance to frontline. How can you make sure that the entire organization is as close to the frontline, as close to the customer as possible and not have these massive chains of information that are oftentimes diluted? And so I think if you're a founder trying to outsource that, you're not really going to be able to build the rest of the organization if you have so little understanding of what persuades a customer.

• 9:20Speaker 01

  So I think you should build the basics of it and then a sales editor can come in and build all the rest.

• 9:24Harry Stebbings?

  What was wrong with the first two reps? A lesson from that, what do you see most founders make a mistake on when they're hiring those first reps?

• 9:31Speaker 01

  They just want anybody in seat. I had this conversation with the founder I advised yesterday and pushed him on it, even though it's uncomfortable. I'm like, look, you know, this guy's got a jumpy resume. I know that you want somebody in seat really, really badly. And he's got some relevant experience, but he's probably not your guy. And I know that advice sucks to hear because you've been trying to fill this seat. But it's so tempting to just try to get a body there. And it's so hard to recruit when you're an early stage startup with no traction, no brand equity. But you just have to hold a really high bar.

• 10:03Harry Stebbings?

  And the pain of getting it wrong is so significant because you'll spend three months searching, six months with them. And then three months searching again and you're like nine months down and you've got nowhere.

• 10:13Speaker 01

  It's one of these lessons, like the founder sort of has to touch the hot stove to really learn that one sometimes. When I'm doing early stage advisory, this is one of the things I'm trying to press on as much as possible. Like, don't take that shortcut.

• 10:26Harry Stebbings?

  So for sales leaders, you mentioned going back to the sourcing side because I do want to go to the funnel of it. Should every sales leader have a branding, be creating content? Because without it, you wouldn't have that sourcing funnel.

• 10:36Speaker 01

  Again, if we go back to first principle, you need some sourcing mechanism. Like, it's the same as you as a VC. One of your comparative advantages is a massive megaphone and a huge funnel because of this content game. But not everybody can play that way and not everybody wants to. And so they can solve that problem separately, but they need to be able to source candidates. You need to be able to create your own funnel.

• 10:59Harry Stebbings?

  So another example would be you came out of an incredible sales division at Databricks or at wherever you name it, and you've got the best Of knowledge from 500 salespeople.

• 11:08Speaker 01

  You can bring some people with you, or if you don't really have those advantages, you have to just go grind it out. And you have to build really compelling messaging and you're sending those LinkedIn messages yourself and your hit rate is going to be lower, but you've got to do it. I have long believed that building audience has compounding advantages. As we've seen, like you're a perfect example of that. And so I got to work on that like six, seven years ago and now it pays off like crazy.

• 11:34Harry Stebbings?

  You said the next stage of the funnel is scorecard. Can you talk to me about scorecard and how you think it builds into building the best sales team?

• 11:42Speaker 01

  This comes back to systems engineering. It comes back to like, do you have a programmatic way to identify the right talent on a consistent basis? In a way that you can then have somebody else do it. Or is this all going to fall apart as soon as you hand it off to your first sales manager, first VP of sales? And so for us, I've been using the framework of the same scorecard for five to eight years and I've iterated on it over time. But it has three components. One is DNA, it's mindset. So what are the intangibles and the things that are fairly intrinsic to the individual? The second piece of that is craft. What does their sales craft look like? And then the third piece is specific knowledge. And depending on the type of sales role that you're filling, your weighting is going to be different.

• 12:25Speaker 01

  I'm hiring SMB reps, so I'm like 70% DNA and mindset. I just want people who have a performance track record of excellence. And I don't care if it was sales or a valedictorian, captain of a sports team, first chair tuba at their like, you know, local orchestra. Like when you do things, do you do it at a really high level? Are they curious? Are they coachable? Are they an absolute grinder? Do they have resilience? There's a bunch in there. And because I'm hiring folks that are early in their careers, 70 to honestly 80% can be just like DNA and I'll teach them the rest. I feel really confident in our sales training program. That's different here for hiring enterprise. If you're trying, hiring legit multimillion dollar quota carrying enterprise reps, you're going to be much more craft and specific knowledge weighted.

• 13:08Speaker 01

  So if you're Databricks, you might have great craft, but you probably need really specific expertise. Or they're going to have a hard time getting up to speed because it's a highly technical product. You need that credibility. My framework is relatively the same, but my weighting will change depending on the role that I'm hiring for.

• 13:26Harry Stebbings?

  Have you made mis-hires owner?

• 13:27Speaker 01

  Oh, yeah.

• 13:28Harry Stebbings?

  When you reflect on them, what should you have seen that you didn't see?

• 13:33Speaker 01

  Something that we've doubled down on recently is references and not taking any excuses for not being able to get the exact references that we want.

• 13:42Harry Stebbings?

  What mistakes did you make? They they gave you references and they weren't okay? Or?

• 13:47Speaker 01

  Or it was not their direct manager. It was like a manager from another team. And we just sort of accepted it because we were trying to move too fast. And now really pressing on like, no, no, no, I need your last two direct managers. Maybe not the one they work for now for obvious reasons. But being really specific there. And if if there's any hesitation or oh, well, like, I don't know if I can get in touch with them, you know, that's a massive red flag. We really want to stress on references.

• 14:13Harry Stebbings?

  Develop that one further. And so you didn't get the references, maybe. And they turned out to be not as good, not as strategic, not as good at sales, not as good at work ethic. Where did they fall down that you should have seen?

• 14:27Speaker 01

  So there were two scenarios like this. One, yeah, it was about values and work approach. We have a company value called bring good energy. And it seems really cheesy, but I think when you're working as hard as we do, and you're you're trying to build something generational, you actually do need people that are going to bring positivity, optimism, enthusiasm, so that, you know, the organization just has a certain mindset. And that wasn't the case. And luckily, this was in person. I caught this on day 11. I was like, hey, this doesn't work like we're done here.

• 14:57Harry Stebbings?

  You will cut it that soon? Wow.

• 15:00Speaker 01

  Yeah, yeah. For things that I don't deem to be coachable. Yeah, I'm gonna try to make a call there ASAP. Same thing a couple of companies ago. There was somebody in the onboarding program who was treating our enablement leader really flippantly and wasn't taking it that seriously. He was a little rude. I just said, get rid of him. If you're already treating this person, you're like supposed to be in your best behavior in weeks, you know, in the early weeks and months. And if that's how that person acts today, then it's only going to be worse later.

• 15:30Harry Stebbings?

  Can you help me? I join ONA. I'm a BDR, SDR, whatever I am, but I'm a junior. What does my first week look like? I think training is done so badly. And often we don't set them up for success.

• 15:41Speaker 01

  Yeah.

• 15:41Harry Stebbings?

  What have been your lessons on how to do? That really well.

• 15:44Speaker 01

  Structurally, we have invested very, very heavily in this. I think one of the things that people find surprising about our business is the headcount allocations. So we've got twenty six AEs and thirty something BDRs and there's five people in enablement. Some of those support other functions like our onboarding and CS functions, but we have a big enablement team for the size of company. We've had enablement since way earlier than most people would tell you.

• 16:07Harry Stebbings?

  How many in enablement?

• 16:08Speaker 01

  Five total.

• 16:09Harry Stebbings?

  Five in enablement. And what's that core role?

• 16:11Speaker 01

  Program building and then some of it is delivery. Our sales enablement manager, he actually runs all of onboarding for new reps. It doesn't really fall to the manager all that much.

• 16:22Harry Stebbings?

  Okay.

• 16:23Speaker 01

  Because the managers are running a million miles a minute, trying to hit the number every single month. And we're bringing in new cohorts of reps every single month between like five and 10 people. We have built and rebuilt a bunch of times this onboarding program. So week one is mostly remote and asynchronous. So they're listening to calls, there's baseline product training, there's stuff about the company, they really get to know our methodology. And then week two, everybody comes in person to Toronto now and we're doing much more practical application. Some of that is done through this tool of Vara, which is like an AI sales simulator that we use. So they're getting tons and tons of practice reps in the sales simulator. And then they're doing live fire reps with our sales enablement manager.

• 17:04Speaker 01

  And so really like practical application, they're building an owner restaurant themselves. They're finding a prospect and doing all the pre-call research, then they're running a mock demo on that exact customer. It's very, very practical. Then they graduate into the team.

• 17:19Harry Stebbings?

  Sorry, I have so many questions. I just want to break them down. But week one, remote async, fascinating. Do you record all calls? I think there's so much value in calls. How do you use calls effectively for training?

• 17:30Speaker 01

  So we have a hall of fame of calls. And I think the important thing is it's not just an entire call. Oftentimes it's call snippets. We use Momentum, which is our call recorder and it's this AI tool that we can find the parts of calls that match our sales methodology the most closely. And then we can pull those clips to show exactly those things. So how to open a call, how to introduce, we have clips for that. How to ask good discovery questions and go two to three levels deeper. You've got examples for that, value prop, how to ask for the sale. It's like all scripted to the word.

• 18:04Harry Stebbings?

  Can we not just hire some monkeys if we just have everything? I mean it in the nicest way.

• 18:08Speaker 01

  Yeah.

• 18:08Harry Stebbings?

  But if we have everything like this is how to open a call, this is how to ask if they're the buyer, this is how to multi-thread, fuck me, AI can do that.

• 18:16Speaker 01

  I don't believe so yet. And for the next little while, here's my big thing with scripting. Scripting the basics enables you to offload that cognitive work. If I'm just thinking about where to take this call next and I don't have a pattern that I've repeated all of these different times, I'm spending all of my cognitive load on low level stuff. Instead, what I need to be thinking of is, okay, so these are the things I learned from my discovery. So this is how I'm going to tailor that in the demo now. And I know this is going to be an issue and I want to ask this question later. So I've got a note about that. I think you can spend your mental energy on higher order things. If you are executing a really like repeatable process, it's the same thing with sports teams.

• 18:59Speaker 01

  Unless you are highly regimented and rigorous and drilled on all of the basics, you can't worry about the most sophisticated tactics and strategies.

• 19:07Harry Stebbings?

  Okay, so week one, they are absolutely taking the notebook and pen out on momentum and learning basically the playbook of what's worked.

• 19:14Speaker 01

  And going through our learning management system. So everything is broken down into modules with specific content and then the examples. So we don't just throw them into the call library.

• 19:25Harry Stebbings?

  In the nicest way, do you find that effective? I mean, I've never met anyone who likes a learning management system.

• 19:30Speaker 01

  Yeah, it works, works for us.

• 19:31Harry Stebbings?

  It works well?

• 19:32Speaker 01

  Yeah, I mean, the content I think is pretty interesting. It's going to get a good facelift and we move them fast. They are getting through a lot and there's check-ins pretty consistently. And they know week two is practical application, so they have to be ready for it.

• 19:48Harry Stebbings?

  So week two, they head to Canada. Okay, so are we fully in person?

• 19:54Speaker 01

  No, no, we still operate primarily as a remote company. And then there's certain roles that we're bringing back into office. I don't think you need your staff, software engineers in an office to do to do their job well.

• 20:06Harry Stebbings?

  I agree. Do you not think you need sales teams in person?

• 20:09Speaker 01

  All of our new SDR and BDR hires are five days a week in office in Toronto now.

• 20:13Harry Stebbings?

  Yeah, I was about to say, I think it's the most important thing.

• 20:16Speaker 01

  And of our recent cohorts, the two newest SDRs both broke the first month record for EMRR sourced.

• 20:24Harry Stebbings?

  So what's EMR?

• 20:25Speaker 01

  Estimated monthly recurring revenue.

• 20:27Harry Stebbings?

  Okay.

• 20:27Speaker 01

  Cause there's subscription plus transaction revenue. So we have an estimate. The two new ones broke the record for first month. The newest BDR in person broke the record for first month. And then the SDRs that are at month two and three both broke the previous records. This is the purely in-person team. So clearly there's been a sizable impact. Just having them all around one another, sitting next to their managers. I'm in the office a whole bunch. I wasn't really supposed to be in the office, but I'm there like three, four days a week just because it's awesome.

• 20:57Harry Stebbings?

  Yeah, no, I listen, I totally agree. I think you need to be. Can I ask, what are the ACVs? I know with transaction it's tougher, but like blended.

• 21:04Speaker 01

  Like eight, nine K.

• 21:06Harry Stebbings?

  A year.

• 21:06Speaker 01

  Mm hmm.

• 21:07Harry Stebbings?

  How do you do like an outbound sales motion with really low ACVs?

• 21:12Speaker 01

  Instrumentation. Common wisdom would tell you that, oh, you can't make outbound work. You can't make a sales-led motion work at these ACVs. Again, that's reasoning by analogy. People aren't thinking from first principles. Okay. Well, why don't you think that's possible? Well, they can't close enough transactions to get that much MRR on a per person basis. Well, why not? Well, if you really look at it, reps and BDR spend 50% of their time doing nonsense. Doing account research and finding leads and filling out their CRM.

• 21:43Harry Stebbings?

  Is that nonsense?

• 21:44Speaker 01

  It's not very valuable. It's valuable at a macro level, but it's not valuable on an individual revenue generation perspective. And so we automate all that. So BDRs don't do any lead research. We centrally manage every lead, every record, do all of the enrichment.

• 22:01Harry Stebbings?

  What do you use for lead research?

• 22:03Speaker 01

  So we built in-house a whole ton of our own tools. Now we also use this company called Datalane. They're like ZoomInfo for SMB essentially. And through Datalane, we get 95% of our leads mobile enriched. So now the economics of your team change drastically. If you previously, before we went on this mobile enrichment campaign, our call to decision maker connect, call to DMC was like 3%. So you'd have to make 100 calls to talk to three decision makers. Yeah, you can't scale. And it's worse if you're going mid-market or selling to corporate.

• 22:36Harry Stebbings?

  Why is it so bad?

• 22:38Speaker 01

  Well, you'd have to be calling a restaurant line, not an office line. People don't pick up their office phone anymore either way. But now our call to DMC is like 13 to 16%.

• 22:49Harry Stebbings?

  How come?

• 22:50Speaker 01

  Because we have mobile phone numbers for everybody. So you're calling somebody's cell phone. And so now BDR making 100 calls can talk to 16 people and be booking two meetings a day, every single day. With good win rates, now two meetings a day, every BDR, half of those closing at like a 9K ACV, the numbers start to really add up.

• 23:09Harry Stebbings?

  Wow, that's fascinating. What percent of converted sales are cold calls?

• 23:13Speaker 01

  Much less today. So we've, we've gone back and forth. When I started, we were 90% inbound and then at some point.

• 23:20Harry Stebbings?

  90% inbound? Wow.

• 23:22Speaker 01

  And then at some point, we were 70% outbound. And then we hired a new head of growth who's done an amazing job. And now we're 60% new inbound. And then we prospect into the base. So former inbounds, the BDRs will go after, plus some cold outbound. Plus, we've got a partner channel now. So there's a channel diversity. So it's ebbed and flowed over the years and it will continue to do that. This is why it is so important to have a multi-channel strategy, in my opinion, so that as certain channels hit saturation or find challenges, you've got other places to go.

• 23:55Harry Stebbings?

  When did you go multi-channel? Cause I think people can go too broad too soon.

• 23:59Speaker 01

  Really early. We built an outbound team in Q4 of 2022 and I started in June. So pretty quickly.

• 24:08Harry Stebbings?

  If you want to do an outbound team well, I'm a founder. I'm like, that girl, I need an outbound team. What would you advise me?

• 24:14Speaker 01

  Depends on a lot, depends on the market and what you're trying to accomplish. I think some generic advice is. Overpay for a BDR who's really good and then give them a path to account executive. There's a lot of companies that are stagnant and there's a lot of BDRs who are quite good that don't necessarily have that path to AE where they're at.

• 24:31Harry Stebbings?

  Can I be a dick? Where do the best BDRs come from? Where do not good BDRs come from?

• 24:37Speaker 01

  You can find good BDRs everywhere. 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? Cause 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. And those people are well-trained salespeople that come into our environment and they rip because our product's great. And so now they have, you know, good sales craft, they've, they've got the grit and now they, you marry that with a number one product in its category and people will take off.

• 25:15Harry Stebbings?

  Okay. And so I just want to go back. So we have like this data enrichment layer, which is super smart. And so when we look at the economics, when it's nine K, you know, I go back to Chris Dagnan, actually, who we both know. And he said that basically you can only have six to eight calls a week. When you think about that for you, obviously yours is a much higher

• 25:33Speaker 01

  Very different.

• 25:33Harry Stebbings?

  Volume scheme.

• 25:35Speaker 01

  Yeah.

• 25:35Harry Stebbings?

  How does yours differ?

• 25:36Speaker 01

  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, 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.

• 25:55Harry Stebbings?

  Three demos per day?

• 25:57Speaker 01

  Every day, yeah.

• 25:58Harry Stebbings?

  Wow. So they're going to do 10 to 12 calls a day?

• 26:01Speaker 01

  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.

• 26:16Harry Stebbings?

  How many net new lead calls do you think your team have a week?

• 26:20Speaker 01

  Hundreds for sure. Yeah. Because 26 account executives, they're probably.

• 26:24Harry Stebbings?

  But like each of them, do they do 20 a week each?

• 26:27Speaker 01

  10 to 20, probably 12 to 18, I bet is, is like.

• 26:30Harry Stebbings?

  But if they have 12 to 18, that would mean every single one of them converts to a demo.

• 26:34Speaker 01

  Every.

• 26:35Harry Stebbings?

  You said they need to have three demos a day.

• 26:37Speaker 01

  Yeah. So the, and the BDRs are booking those for them.

• 26:40Harry Stebbings?

  Ah, I got you. Okay. Got you. Okay. So the BDRs book them. How many BDRs do we have?

• 26:46Speaker 01

  Thirty five ish today.

• 26:47Harry Stebbings?

  And so thirty five, book three net new each or?

• 26:50Speaker 01

  Just call it two, call it two.

• 26:52Harry Stebbings?

  Two each?

• 26:52Speaker 01

  Yeah.

• 26:53Harry Stebbings?

  Wow.

• 26:53Speaker 01

  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 could be doing five to 10 because it's, it's a higher intent.

• 27:06Harry Stebbings?

  Should AEs be responsible for pipeline generation?

• 27:09Speaker 01

  In SMB, I 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 and enterprise, have to do some prospecting, but it's not banging the phones.

• 27:33Harry Stebbings?

  No offence, BDRs, if they're paid like shit, which respectfully they are, aren't you always just gonna get bad people? No offence. And again, like they're the frontline of your company. How do you think about effective BDR hiring, given they are more junior?

• 27:47Speaker 01

  They 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. And 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, it's bad comp.

• 28:12Harry Stebbings?

  How do you think about target setting with them? Because I always think that incentives can be gamified. So you can do like demos booked. Sure, but I could just fudge the qualification process and get you a load of donut shops that are shitting going out of business. Not gonna help.

• 28:26Speaker 01

  So our BDRs only get paid on closed one business. Mm hmm. Alignment. Our account executives only get paid when their customers go live. We are month-to-month contracts. So we wanna make sure that our account executives are doing high-quality handoffs, setting good, setting good expectations or closing high-quality customers. And so again, they are highly incentivized to make sure that those customers are good so that they go live.

• 28:50Harry Stebbings?

  And that comp doesn't include transaction revenue?

• 28:54Speaker 01

  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. So 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.

• 29:16Harry Stebbings?

  Wow. Does that ever get you in trouble? And what I 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're way off it.

• 29:26Speaker 01

  Nah, 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 eGPV, which means they are going to be more focused on the higher value customers for the business. Our estimated MRR on a per deal basis went up pretty significantly.

• 29:46Harry Stebbings?

  What is a good ratio? Say you pay an AE, I'm just making it up, like 200K. Is it five to one? Is it in terms of like revenue booked? What is good?

• 29:56Speaker 01

  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 it's inbound.

• 30:07Harry Stebbings?

  So what are you at?

• 30:08Speaker 01

  A good account executive, like our inbound account executives close 250K ARR every month.

• 30:15Harry Stebbings?

  Wow.

• 30:16Speaker 01

  So it's a little different because we're not signing.

• 30:18Harry Stebbings?

  That means they basically close a client a day?

• 30:20Speaker 01

  Yeah, or more, more in a lot of cases.

• 30:22Harry Stebbings?

  Wow.

• 30:23Speaker 01

  Efficiency. This is the thing. So when people talk about, well, you know, one of the things that surprises people is on the outbound side, we have two BDRs for every account executive. Oh, 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 and L inside out and backwards? And do you understand the inputs and outputs of your unit economics?

• 30:53Harry Stebbings?

  Where do most revenue leaders misunderstand their P and L?

• 30:57Speaker 01

  They don't even understand it. They don't know where to start. They think it's the domain of of finance and finance gives them a headcount number. And they say, you have seventeen reps and you have to do this. And they say, okay. Or they get the number and they just complain about it, but they don't really understand sell by sell. The ARR model that we have, I understand it sell by sell every single input. Cause I own demand gen 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?

• 31:41Speaker 01

  And I'm always trying to layer in more than I actually anticipate we'll need because one channel will falter. Something weird will happen, but then on a 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 VPs 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, 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.

• 32:27Harry Stebbings?

  What channel has outperformed expectations? And what do you learn from that?

• 32:31Speaker 01

  Organic, probably.

• 32:33Harry Stebbings?

  What do you think you did well to inspire organic to do so well?

• 32:37Speaker 01

  I did nothing.

• 32:39Harry Stebbings?

  Never start with that. Always it was me. It's the takeaway, but yes.

• 32:42Speaker 01

  Yeah, this was a founder insight. This is Adam having an incredibly deep understanding of the customer and the market and way before it made economic sense, he was all in our organic. Adam just has like such an intuitive understanding of our customer base. And he was like, we're all in on YouTube. We are going to be the central hub for restaurant marketing. No one owns this position online. And so we hired people that manage the YouTube experience for like 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.

• 33:18Harry Stebbings?

  That's a really bold leader because you have to basically be comfortable losing money without guarantee that the rewards will come.

• 33:26Speaker 01

  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. That happens like 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.

• 34:07Harry Stebbings?

  Do you not think this is where marketing completely blends with sales? So 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.

• 34:20Speaker 01

  A hundred percent. This is something that a lot of folks get wrong is they like squabble over attribution. They'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 rolls 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. So we don't worry about it.

• 34:58Harry Stebbings?

  What channel has sucked when you thought it would be good?

• 35:01Speaker 01

  We just tried CTV and didn't have a ton of success with it. Connected TV, connected TV. So running pre-roll ads on Amazon Prime or the like set top boxes.

• 35:11Harry Stebbings?

  What do you think happened there?

• 35:12Speaker 01

  Really what happened is we've got too many other things that are successfully taking off and we just diverted resources.

• 35:17Harry Stebbings?

  Was it expensive?

• 35:18Speaker 01

  Wasn't that bad. That's the cost of experimenting. You know, 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. And 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.

• 35:39Harry Stebbings?

  What are your sales cycles?

• 35:41Speaker 01

  A lot of one call closes, but average sales cycle's under a week.

• 35:45Harry Stebbings?

  Under a week. How is that the case? I mean that with the most respectful. That is extraordinary.

• 35:51Speaker 01

  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 if folks are willing to move on it. But something else we do that I think helps a ton. The 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 on 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. And 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.

• 36:34Speaker 01

  But here's what you need to know about what's different than us and our competitors. We are going to give you way less flexibility and customization. If that's your main priority, owner's 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 and A B 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.

• 37:18Speaker 01

  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 going to work. And so what happens is the wrong customers opt out immediately. And 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 upfront, 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 Taco 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.

• 38:02Harry Stebbings?

  When you're selling to SMB and mum and pop, how many want customization?

• 38:07Speaker 01

  Some for sure.

• 38:09Harry Stebbings?

  Really?

• 38:09Speaker 01

  Yeah, and we have some larger brands, ten, twenty, thirty 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.

• 38:21Harry Stebbings?

  Do you have a constant internal battle of how far into enterprise you go?

• 38:26Speaker 01

  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 thirty location brand, but we are against working with a brand that wants high degrees of customization. More of those brands are going to want more flexibility and choice and are going to be, are just going to say, oh, actually, this isn't the right fit. But, you know, we closed a thirty three location chain the other day and they came to us and they're like, yeah, I don't, I don't want to deal with all this stuff. I just want somebody else to figure it out for me. Okay, great. Here.

• 38:58Harry Stebbings?

  But if you look at Olo, if we're blunt, why are they not a good business where you are?

• 39:02Speaker 01

  Hmm, they're playing a different game. They're playing a very different game.

• 39:06Harry Stebbings?

  I'm sorry, I'm naive. How so?

• 39:08Speaker 01

  Well, they're way up market. They're trying to win enterprise brands and they're trying to play the customization and flexibility and the headless game. And tons of cost pressure there from these major franchises. I 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.

• 39:26Harry Stebbings?

  When you look at how you run your internal processes today, there's, there's real velocity slash action to your sales cycles. They're very fast compared to others. How do you do pipeline generation meetings? How do you do deal reviews? What are the staple meetings in a sales week at Oner?

• 39:42Speaker 01

  So we don't do pipeline review.

• 39:43Harry Stebbings?

  Okay. Why?

• 39:45Speaker 01

  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? What do we project from the BDR team? And we can drive to that number. So it's really about butts in 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. In enterprise, obviously it does, and you're going to do in weekly scrutiny on every deal and stress testing it. But for us, I can understand everything I need about the business basically from the sales force.

• 40:26Harry Stebbings?

  What's your ramp time on that, on new A's?

• 40:30Speaker 01

  So we've interestingly extended this recently.

• 40:33Harry Stebbings?

  Why?

• 40:35Speaker 01

  Uh, we wanted AEs to start in the role, uh, 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.

• 41:03Harry Stebbings?

  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. Like, you can't afford to. Do you not bluntly have such a big universe like you can get them on the call earlier and not fuck it up?

• 41:22Speaker 01

  There's 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.

• 41:45Harry Stebbings?

  Do you do shadowing? Like, were you, were sales leaders drawing calls for the first call, second call, third call?

• 41:50Speaker 01

  Oh yeah, big time.

• 41:51Harry Stebbings?

  Do you want to me about that? Because again, dude, I've never run a sales team. That's why these shows are successful because I ask the questions that everyone who has no idea what they're doing asks too. How do you do that? When do you hand off?

• 42:03Speaker 01

  The reps will go through the training and then 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, do you know how to use Salesforce and all the other stuff? And then their first calls, the managers are on all of them, basically. And 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 a few discovery questions, do a little bit of the demo before they get that deer in headlights look. And then the manager can jump in and take it over. So we see a lot of like manager close deals in that first couple of weeks.

• 42:40Harry Stebbings?

  In the nicest way, how sophisticated are the clients? And what I mean by that is if you're a mom and pop shop with maybe a couple of Chinese stores or a couple of Indian rations, are you really like jumping onto like sales demo calls from a plush office? Being like, oh, thank you, Carl and Jessica. Lovely to see you. Are you like, hey? Why are you bothering me?

• 42:58Speaker 01

  Yeah.

• 42:58Harry Stebbings?

  Fuck off.

• 42:59Speaker 01

  A lot of people are joining the Google Meet from their phone. They're in the back office. Smoking a dart is not an uncommon experience on 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 wherever we need to meet.

• 43:15Harry Stebbings?

  How important is it to go in person?

• 43:17Speaker 01

  We don't do any in person.

• 43:18Harry Stebbings?

  You don't do any in person? Alabell, why?

• 43:23Speaker 01

  The economics don't make sense. We're so efficient running the sales cycle digitally.

• 43:28Harry Stebbings?

  I'm not being rude. If you go to like a highly dense metropolitan area, there are not like fifty mom and pop shops in a square. And you can like.

• 43:36Speaker 01

  So we are highly targeted. I mentioned that we have these two M L 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.

• 43:51Harry Stebbings?

  Wow, this is fascinating. What size restaurant is interesting?

• 43:54Speaker 01

  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 five hundred bucks a month.

• 44:03Harry Stebbings?

  And you don't want churn.

• 44:04Speaker 01

  Yeah.

• 44:05Harry Stebbings?

  Obviously, okay.

• 44:05Speaker 01

  Exactly.

• 44:06Harry Stebbings?

  So they're doing like five hundred K to five million.

• 44:08Speaker 01

  Yeah. And so we know that there's certain G P V 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 fifty doors.

• 44:22Harry Stebbings?

  Don't laugh. Is the likelihood of closure greater in different cuisine types? So if your G P V is under three hundred grand for Indian, but under seven hundred grand for Italian, is it different in that way?

• 44:34Speaker 01

  I don't know. We haven't run that analysis.

• 44:35Harry Stebbings?

  That would be fascinating to see that, oh, the Italians, they close under a million. The Chinese, they're better on five hundred K.

• 44:41Speaker 01

  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.

• 44:53Harry Stebbings?

  Got you, because you don't want to spend a ton of resources if the churn's too high. Mm hmm. Okay.

• 44:57Speaker 01

  And so going back to your question about 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 rep basis than those companies.

• 45:31Harry Stebbings?

  Thing that 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.

• 45:40Speaker 01

  Yeah.

• 45:41Harry Stebbings?

  It's fascinating. So we have that with different stages of sales come different challenges.

• 45:49Harry Stebbings?

  You guys scaled really fast. I mean, how fast did you scale to 10 million in revenue? What were you at when you joined?

• 45:55Speaker 01

  Two and a half.

• 45:55Harry Stebbings?

  You're at two and a half.

• 45:57Speaker 01

  We're at like 40 today. Yeah.

• 45:59Harry Stebbings?

  Fucking miss.

• 46:00Speaker 01

  Under, under three years. Yeah, and we're actually growing faster today than we were.

• 46:04Harry Stebbings?

  Three years to 40 million.

• 46:06Speaker 01

  Yeah, two and a half to that. Yeah. And we're actually growing faster today. And so I'm very optimistic about what this year will bring.

• 46:14Harry Stebbings?

  Does customer acquisition get cheaper over time? Because you have brand, you have word of mouth, you have a humming sales and marketing team. Or does it get more expensive as you expand beyond your core ICP?

• 46:28Speaker 01

  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, 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 upfront. Rev ops, enablement, data and biz ops, like 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 on demand gen, that flywheel is, is pretty tough to stop.

• 47:10Harry Stebbings?

  What is the biggest thing that RevOps has done to make a humming and efficient machine, do you think?

• 47:15Speaker 01

  A few things. So one is trying to automate and obfuscate all of the low value stuff. So we use Momentum that looks at the transcript of every single sales call and it fills in the Salesforce fields for the rep. It 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 rep 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. Like I think sometimes

• 47:56Speaker 01

  the pre-sales gets all of the investment and post-sales doesn't, but a company that I know you knows Pavlov and they're, I was, we were their first customer. Yeah, Mark and I worked together very closely at Shopify.

• 48:08Harry Stebbings?

  I didn't know that.

• 48:09Speaker 01

  I had dinner with him last night.

• 48:10Harry Stebbings?

  You know, we led that round.

• 48:11Speaker 01

  I do.

• 48:11Harry Stebbings?

  Oh, wow. Fantastic. I should have known that.

• 48:16Harry Stebbings?

  I love him. He's so good.

• 48:17Speaker 01

  They're an awesome team. I'm very bullish. And so we're using a tool like Pavlov to post-sale, incentivize the customer to take actions that we know lead to higher G P V, 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.

• 48:42Harry Stebbings?

  How do you think about that? Like, how do you do that successfully? Because, you know, as you said, there's the SaaS revenue, which is great, but also transaction revenue is a 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?

• 48:57Speaker 01

  Again, it goes back to data and infrastructure. So one of the things that the Biz Ops team did is build a scoring model for customer configuration quality. So it's called the Growth Potential Score. So 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 G P V, drive growth. And 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 G P score, the Biz Ops team does. And so we, 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 G P score, they can see all the G P.

• 49:39Harry Stebbings?

  Sorry, what's a launch specialist?

• 49:41Speaker 01

  An onboarding rep.

• 49:42Harry Stebbings?

  Okay, and so what do they do?

• 49:44Speaker 01

  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.

• 49:58Harry Stebbings?

  Wow.

• 49:58Speaker 01

  Mm-hmm.

• 49:59Harry Stebbings?

  It's quite cheap, isn't it? Like 500 bucks a month, if you actually think about it. Six grand a year, I'm with you, but everything you get feels pretty good.

• 50:08Speaker 01

  It's a pretty good deal.

• 50:09Harry Stebbings?

  Yeah.

• 50:09Speaker 01

  And a bunch of these customers end up making...

• 50:12Harry Stebbings?

  But I'm thinking like the margins are not great then. Because if you've got like a launch specialist doing all of that shit, making menus, domains, making sure sites up to quality for them, they're happy with color schemes and the fonts and...

• 50:25Speaker 01

  They do a lot of launches every month on a per person basis.

• 50:28Harry Stebbings?

  How many launches do they do?

• 50:30Speaker 01

  Over 20 per person. Plus, they're Latin American based.

• 50:34Harry Stebbings?

  Are they comped on a launch basis?

• 50:37Speaker 01

  Yeah. And going back to this growth potential score thing, so 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 of and quality of those photos? What's the story we tell? Or do we have connection to their Google's business profile? Or have we done all the business listings work? Is the SEO done properly? All that stuff is, again, delivered programmatically.

• 51:04Harry Stebbings?

  You said they're Latam based. Talk to me about that. Are they internal resources?

• 51:09Speaker 01

  Yeah.

• 51:09Harry Stebbings?

  Okay, why Latam based? It's like a pricing arbitrage?

• 51:12Speaker 01

  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 arm's length type thing. We've made them part of our team, they're...

• 51:27Harry Stebbings?

  How? That's pretty hard to do.

• 51:29Speaker 01

  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 and outbounding into these markets, 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, we interviewed hundreds and hundreds of people and found a system to basically identify good folks.

• 51:57Harry Stebbings?

  How many do you have in Latam?

• 51:58Speaker 01

  Seventy people, probably.

• 52:00Harry Stebbings?

  Wow, how big is the company now?

• 52:02Speaker 01

  Uh, approaching 250.

• 52:03Harry Stebbings?

  Fuck. What breaks with scale?

• 52:06Speaker 01

  Everything.

• 52:09Speaker 01

  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, there's a long period of time where tons of people reported directly into me. ICs did and then managers did. And so I was really close, like within arms' reach of every person in the org. And now there's multiple layers between me and any IC.

• 52:32Harry Stebbings?

  Is that good? You know, we 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?

• 52:42Speaker 01

  Well, I still get on demos almost every week.

• 52:44Harry Stebbings?

  You do?

• 52:44Speaker 01

  Oh, 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 the reps are like, oh, like you said this and this, like I'm going to do that. Can you send me? Can you send me how you're thinking about it? We like quickly sketched out some, because I've had these new ideas. The best way to figure out if they work is do them myself. So I'm pretty intentional about staying connected. My BDR manager rips dials himself. The AE director runs demos still.

• 53:26Speaker 01

  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.

• 53:32Harry Stebbings?

  What bit of the machine keeps you up at night?

• 53:35Speaker 01

  Talent acquisition. Yeah, because it's really hard.

• 53:38Harry Stebbings?

  As specific as possible, I'm so sorry, but is it BDR acquisition? Is it launch specialist acquisition?

• 53:44Speaker 01

  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 were 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 SDRs starting next month just from this and then another four in July. And so.

• 54:27Speaker 01

  Again, like it comes back to this theme of how can you hit today, but also think about tomorrow?

• 54:32Harry Stebbings?

  We'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?

• 54:43Speaker 01

  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.

• 54:57Harry Stebbings?

  Do you think Rapsacoin operates?

• 54:59Speaker 01

  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 their mission motivated. I 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.

• 55:17Harry Stebbings?

  If I came to you and said, I don't give a shit about the mission, just to be honest, I care about making money and I'm going to crush quota and I'm going to be here night and day crushing quota.

• 55:27Speaker 01

  Makes me nervous.

• 55:28Harry Stebbings?

  Does it?

• 55:29Speaker 01

  Yeah.

• 55:29Harry Stebbings?

  Why?

• 55:30Speaker 01

  They'll just go to the next thing where they get offered more money.

• 55:33Harry Stebbings?

  Is that not okay if I crush quota for you for two years?

• 55:35Speaker 01

  I might not even get two years out of them if that's the case, especially 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 going to 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 cramps. 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. You can read any of the engagement research and get this stuff.

• 56:18Speaker 01

  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 as a just push, push, push, push, push, push, then you take. The way 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. So community recognition, autonomy, mastery, mastery is do they feel like they are on the path to 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.

• 57:00Speaker 01

  And then the S is steps. So do they have a steps is 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 hire basically whoever I want now from this market. We promote heavily from within because I think that's such an important engagement driver.

• 57:26Harry Stebbings?

  You're scaling into a new phase of sales leadership for you. What are you nervous about as you scale yourself as a sales leader?

• 57:34Speaker 01

  That's a really good question.

• 57:36Harry Stebbings?

  I'm a podcaster.

• 57:38Speaker 01

  A good one at that.

• 57:40Harry Stebbings?

  I go on dates and girls like, that's, that's a really good question. I'm like, I have had practice.

• 57:47Speaker 01

  I had an old boss who 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? I'm sort of scared of it all and that is like a really positive motivation.

• 58:08Harry Stebbings?

  What did you do that you wish you hadn't done?

• 58:11Speaker 01

  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.

• 58:23Harry Stebbings?

  Jason Lemkin 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?

• 58:34Speaker 01

  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. And we're going to give you a lot of coaching and a lot of feedback and we want you executing on our system.

• 58:46Harry Stebbings?

  Yeah, very systematized, like not much room if you want to bring a new flavor of sales respectfully.

• 58:51Speaker 01

  There's freedom within a framework. I want people to have some creative freedom, but it's got to be within a methodology.

• 58:56Harry Stebbings?

  You know, when your wife says, do you know, of course you can go out with the boys. It's your choice. That's, that's kind of the same thing.

• 59:04Harry Stebbings?

  Oh, I think I'll stay in actually. Yeah.

• 59:07Speaker 01

  And so I think more senior reps come in and like, I know how to do this. I'm good. I'm going to 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 skillset. 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. You're going to get coached every single week.

• 59:52Speaker 01

  Every month you get a monthly report card that talks about what you did well and where the areas of development. And then you develop your secret sauce. 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, nah, I'm not about this.

• 1:00:15Harry Stebbings?

  So that's what you had done that you wish you hadn't done? What have you not done that you wish you had done?

• 1:00:21Speaker 01

  I wish I had been more insistent about hiring a head of applied AI.

• 1:00:27Harry Stebbings?

  What?

• 1:00:28Speaker 01

  We're just hiring this role right now. I have become absolutely obsessed with all things AI. Like as soon as ChatGPT 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.

• 1:00:51Harry Stebbings?

  You sound like a riot on a Friday night.

• 1:00:54Speaker 01

  I've actually.

• 1:00:55Harry Stebbings?

  Remind me to reserve my calendar.

• 1:00:59Harry Stebbings?

  Sorry, dude.

• 1:01:00Speaker 01

  I actually vibe coded in an app on a Friday night a couple, a couple of weeks ago. So you're not wrong. Stevie 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, 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-

• 1:01:38Harry Stebbings?

  Respectfully, why? Why do you need custom AI versus off-shelf AI application?

• 1:01:43Speaker 01

  Could be off-shelf. We're using a lot of off-shelf stuff, but somebody has to think about, okay, that entire ecosystem, is this builder buy? And how is it all getting weaved together in a really cohesive manner? I'm pushing on my, our rev ops 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.

• 1:02:06Harry Stebbings?

  Wow. What do sales teams do today that there's no way they'll do in five years' time?

• 1:02:11Speaker 01

  Account research, lead prep, lead research, figuring out who to call. I think it's insane that companies do that today, that they have BDRs doing manual lead research. If 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.

• 1:02:29Harry Stebbings?

  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 AISDR tools. I mean, do we, I, I, I was laughing with the team because obviously I'm an investor for a living too. Um, I think we've seen 15 AISDRs in a week. That's just what we've seen in a week.

• 1:02:53Speaker 01

  You see these massive trends and, and ultimately that advantage gets competed away. Same thing with sales engagement. When I, I 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, 5X'd 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.

• 1:03:26Harry Stebbings?

  God, Aaron Ross.

• 1:03:28Speaker 01

  Oh, yeah.

• 1:03:28Harry Stebbings?

  Fuck me, that takes me back.

• 1:03:30Speaker 01

  Mm hmm. But that playbook was incredible when it first broke and then everybody started doing it. And then it stopped working. And 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. And yeah, I still think there's a tremendous advantage with some of this generative AI outbound. It will get competed away and.

• 1:03:50Harry Stebbings?

  A tip for all sales leaders that I think they should do is leverage podcasts to acquire customers and speak to stakeholders. So what I mean by that is, you know, we have an amazing company that sells to patent lawyers.

• 1:04:02Speaker 01

  Yeah.

• 1:04:03Harry Stebbings?

  Interview the partners at the largest patent law firms and talk about their challenges.

• 1:04:08Speaker 01

  Yeah.

• 1:04:08Harry Stebbings?

  How they think about the future, da, da, da. Don't sell the company at all. And then after the show, they'll be like, so what do owners do?

• 1:04:15Speaker 01

  Yeah.

• 1:04:15Harry Stebbings?

  And you're like, oh, sure. Let me tell you for five minutes. You do one a week. You've got fifty two leads a year.

• 1:04:20Speaker 01

  I met a guy who generates sixty 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 posts the episode on their podcast and.

• 1:04:41Harry Stebbings?

  I'm on Owners, the manual podcast, and I'm so excited. And then all of the competitors are like, oh, my God, what the fuck is that?

• 1:04:49Speaker 01

  It's a great strategy.

• 1:04:49Harry Stebbings?

  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.

• 1:05:01Speaker 01

  Yeah.

• 1:05:01Harry Stebbings?

  Versus tweeting or blogging or doing any of that shit, it's still quite hard.

• 1:05:05Speaker 01

  But even that is a nothing investment. What's a podcast like two hundred and something bucks and?

• 1:05:11Harry Stebbings?

  I have no idea, but not much. No, I completely agree with you.

• 1:05:13Speaker 01

  My entire home studio setup was like two grand.

• 1:05:16Harry Stebbings?

  I completely agree with you, but people are lazy. They are, and it's still much harder than posting on LinkedIn.

• 1:05:24Speaker 01

  Yeah, you're not wrong.

• 1:05:25Harry Stebbings?

  And my favorite thing about secrets is you tell the world and people still don't listen. Do you know what I mean?

• 1:05:31Speaker 01

  People ask me this all the time. They're 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 gonna do it that well. This was something from Stevie, like, execution is the only mote, and I'll always execute, out execute these folks.

• 1:05:48Harry Stebbings?

  Yeah.

• 1:05:48Speaker 01

  I'm a hundred percent 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.

• 1:06:08Harry Stebbings?

  My, my mother, actually, I walk with her every weekend, a marathon, and she always says, what the fuck, like, why are you telling everyone to do this and to do what you do? And I'm like, cause I'm telling them that I'm making spaghetti bolognese. I 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 buys the bolognese mix and the pasta. The other makes the fresh pasta 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, it doesn't fucking matter if I do the podcast.

• 1:06:52Speaker 01

  Yeah.

• 1:06:52Harry Stebbings?

  It's how you do what you do.

• 1:06:53Speaker 01

  And again, this comes back to first principles reasoning. You know, people are gonna 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 gonna do AI lean 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. Execution is the, is the whole piece.

• 1:07:27Harry Stebbings?

  Do you think it's valuable to have competitors in your head? Like, do you like to inspire teams with like, hey, we're beating X competitor?

• 1:07:34Speaker 01

  We don't that much. Yeah, we'll joke around about it, but it's not really like our driving motivation. It is the mission. Like, it's easy to feel good about helping like 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 six grand more a month, which, you know, it doesn't seem like a lot of money. But if you're a restaurant owner and your 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

• 1:08:18Speaker 01

  Which competitor do you most respect? I have a lot of respect for Toast. Good product craft. Their GTM execution is really good. They operate in a pretty like respectful way, too. Like, we don't find Toast doing shenanigans to their customers. I think like the competitors that I have complete disregard and disrespect for, the ones that treat their customers poorly. Because these are SMBs and you're like 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 monger as they're, they're trying to leave your That's really inexcusable, especially when it's like 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.

• 1:09:02Speaker 01

  You know, in the short term, I'm sure it's helped them hold on to some deals and stem some churn here and there, but none of those customers feel good about that relationship. And again, 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 optimized for the long term. Like, why don't we lock customers into year-long contracts? We probably could. Well, we want to 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

• 1:09:43Speaker 01

  advantage. Like, we, 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.

• 1:10:07Harry Stebbings?

  Dude, I want to move into a quick fart. I could talk to you all day. You are advising a twenty-three-year-old. I'm your little brother, okay? And I'm twenty-three, and I've got my first job in sales. I'm a rep. What do you advise me, knowing all that you know now, entering this workforce?

• 1:10:22Speaker 01

  Mm-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 the outcomes will eventually come.

• 1:10:37Harry Stebbings?

  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?

• 1:10:45Speaker 01

  That's a really good question. We had a pretty good one recently. On Wednesday, the end of April, we had to like 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. I 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 twelve fifteen 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.

• 1:11:24Speaker 01

  And even at ten thirty, there was BDR still making calls to the West Coast to try 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 was already at their number. They didn't really have to do it for themselves. And I think that is a special part of Owner's DNA. Yeah, we have people that are very individually motivated, but this like collective is pretty special.

• 1:11:49Harry Stebbings?

  What have you changed your mind on most in the last twelve months? I think ChatGPT and OpenAI are unwaveringly the dominant leader for the next ten years, and I think they'll be a two trillion dollar company. I questioned actually that in the early days.

• 1:12:01Speaker 01

  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. I mentioned how I wanted to hire this head of applied AI earlier. I started playing around with O3 and I updated a bunch of my like chat GPT workflows to use O3. And I was just like, holy crap, this is so different. The memory, the reasoning, like the, 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.

• 1:12:39Harry Stebbings?

  You can take Jason's side or Rory's side on who is right. Is AI going to bring mass unemployment in a way that we haven't seen before?

• 1:12:49Speaker 01

  I don't think so because of Jevon's paradox. You saw this argument as compute got cheap. Well, all these foundation models going to be less valuable. It'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 Jevon's paradox may lead to high employment.

• 1:13:32Harry Stebbings?

  How do you motivate sales teams when numbers are missed?

• 1:13:36Speaker 01

  It'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, 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 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.

• 1:14:16Speaker 01

  And failure is the journey. That's, that's what helps us get better as people. That's what helps us grow and, and develop ourselves. Then when you inevitably have these down periods, you're prepared for them mentally. Like we vaccinated people against those difficult times.

• 1:14:32Harry Stebbings?

  Tell me, Owner, twenty thirty five, ten years out, where is Owner then?

• 1:14:37Speaker 01

  I think we'll be a, 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. I think he's got all of, 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 like, I want to be one of the handful of people that have taken a company from early to, to IPO. You need an incredible team and 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.

• 1:15:21Harry Stebbings?

  Dude, I have loved this. Uh, I, I'm so appreciate you sending over your thoughts. 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. So thank you so much.

• 1:15:33Speaker 01

  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, uh, this was a blast.

• 1:15:43Harry Stebbings?

  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 changed their organizations because of shows like this. Let me know what you think. You can email me harry at twenty vc.com. But before we leave you today, if you're ready to leave rigid payment terms behind, Capchase is here to change the game. Capchase brings B to C buying convenience to B to B software and hardware purchases. Capchase offers your buyers the flexibility they demand on annual and multi-year contracts. While you get paid upfront every time, this means faster closings, higher deal sizes, and a streamlined process without the hassle of discounts or collections.

• 1:16:23Harry Stebbings?

  Over 2,000 companies already use Capchase to accelerate their sales and secure predictable revenue. It's time to unlock your team's full potential. Try Capchase on even just one deal you've lost over price or terms. No obligations, no platform fees, and no heavy implementation. Visit capchase.com/20vc today and turn payment friction into your competitive edge. And when it comes to sales, timing is everything. But if you're relying on outdated CRM data, you're probably already behind. And that's why today's most innovative companies trust go-to-market intelligence to fuel their AI-powered growth. Ready to join them? ZoomInfo is hosting an interactive online summit in May that will help you get the competitive edge you need to stay ahead of competition.

• 1:17:07Harry Stebbings?

  Find out how leaders in AI and go-to-market are building their growth engines and get practical advice, including hands-on demos of cutting-edge AI tools from ZoomInfo, the go-to-market intelligence platform that makes every seller your bestseller. Learn more and subscribe to be the first to know when registration opens at zoominfo.com/20vc. And if ZoomInfo helps you find the right opportunities, Otter AI makes sure you close them. Hey, managers and leaders, want to make your meetings way more efficient and save time? With over a billion meetings processed, Otter AI is the ultimate AI meeting productivity tool. It gives you real-time transcripts, quick summaries, action items, and insights,

• 1:17:49Harry Stebbings?

  plus a voice-activated agent that keeps you focused and productive. It's unbelievable. Imagine cutting down your meeting prep and follow-ups and freeing up more time for what matters. Otter is trusted by over 25 million users, including Fortune 500 companies, to boost productivity and collaboration. So are you ready to take your meetings to the next level? Well, head over to get.otta.ai/20vc and grab a 30% discount. My word, they're so generous. When you subscribe to a business plan for your team, that's get.otta.ai/20vc. Let's make your meetings work for you. As always, I so appreciate all your support and I cannot wait to bring you an incredible episode with Varun at Windsurf on Monday.