# 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

20Sales · May 30, 2025 · 79 min · 15,406 words
Speakers: Harry Stebbings, Kyle Norton
Source: https://www.996.fm/episodes/20vc--ep-9e41f1fc/

## Cold open

**Harry Stebbings** [0:00]:

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 scaled revenue from 2,000,000 to 40,000,000 in ARR in under three years while selling to one of the hardest markets, SMB restaurants. Before Owner, Karl led sales at Shopify, where he helped architect one of the most operationally elite GTM orgs in SaaS. And Karl is really known for turning sales orgs into machines. At Owner, he systematized this incredible revenue engine 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 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. 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 Cap Chase on even just one deal you've lost over price or terms. No obligations, no platform fees, and no heavy implementation. Visit capchase.com forward slash two zero v c 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 But if you're relying on outdated CRM data, you're probably already behind.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. 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 best seller. Learn more and subscribe to be the first to know when registration opens at zoominfo.comforward slash 20v c. And if ZoomInfo helps you find the right opportunities, Otter dot ai makes sure you close them. Hey. Managers and leaders wanna make your meetings way more efficient and save time? With over a billion meetings processed, Otter dot ai is the ultimate AI meeting productivity tool. It gives you real time transcripts, quick summaries, action items, and insights, 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's trusted by over 25,000,000 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.otter.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 getotter.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.

**Kyle Norton** [3:34]:

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

**Harry Stebbings** [3:40]:

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?

**Kyle Norton** [3:53]:

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, 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 reforge course. Did you become a better sales leader through product knowledge? A thousand percent. How? So much of building a great go to market organisation is systems engineering. I'm sure we're gonna talk about this a ton today, and product management and building product is that. 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 Cagan's vision setting template. And so like I only discovered these things

**Harry Stebbings** [5:00]:

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

**Kyle Norton** [5:04]:

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 efficiency? 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 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.

**Harry Stebbings** [6:08]:

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 wanna 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. Mhmm. If we start at the beginning of the funnel, sourcing Yeah. What are your biggest lessons on what it takes to source amazing sales talent?

**Kyle Norton** [6:32]:

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. That's And 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, 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.

**Unknown** [7:27]:

Was the quality high?

**Kyle Norton** [7:28]:

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 Braden. Then from that same company now, there's nine people that work at Owner. From the office.

**Harry Stebbings** [8:01]:

Wow, bet they're thrilled with you. When did you join Owner in terms of sales team stage? There

**Kyle Norton** [8:08]:

was a manager and four reps. Manager and four reps. Yeah, we parted ways with two of those reps fairly quickly, and then we've built to, I think 60 folks in sales today.

**Harry Stebbings** [8:17]:

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? So not to get

**Kyle Norton** [8:25]:

into semantics, but

**Harry Stebbings** [8:26]:

it really depends on what you mean by playbook. Basically, a framework for what customers want Yeah. Where they get it, how to message them, and what a standard sales cycle looks like with a price coverage.

**Kyle Norton** [8:38]:

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 talking 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 gonna 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? So I think if you're a founder trying to outsource that, you're not really gonna be able to build the rest of the organization if you have so little understanding of what persuades a customer. So I think you should build the basics of it, then a sales leader can come in and build all the rest.

**Harry Stebbings** [9:24]:

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

**Kyle Norton** [9:31]:

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. 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.

**Harry Stebbings** [10:03]:

And the pain of getting it wrong 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.

**Kyle Norton** [10:13]:

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. Don't take that shortcut.

**Harry Stebbings** [10:26]:

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

**Kyle Norton** [10:36]:

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 was 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.

**Harry Stebbings** [10:59]:

So another example would be you came out of an incredible sales division at Databricks or at

**Kyle Norton** [11:04]:

wherever

**Harry Stebbings** [11:04]:

you name it, and you've got the best mafia of knowledge from 500 salespeople.

**Kyle Norton** [11:08]:

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 your self, and your hit rate's gonna be lower, but you gotta 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.

**Harry Stebbings** [11:34]:

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?

**Kyle Norton** [11:42]:

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 gonna 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 specific knowledge. And depending on the type of sales role that you're filling, your weighting is gonna be different. 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 if you're hiring enterprise. If you're trying hiring legit multimillion dollar quota carrying enterprise reps, you're gonna be much more craft and specific knowledge weighted. So if you're Databricks, you might have great craft, but you probably need really specific expertise or they're gonna 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.

**Harry Stebbings** [13:26]:

Have you made mishires at Owner? Oh, yeah. When you reflect on them, what should you have seen that you didn't see?

**Kyle Norton** [13:33]:

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.

**Harry Stebbings** [13:42]:

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

**Kyle Norton** [13:47]:

Or? 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, don't know if I can get in touch with them, you know, that's a massive red flag. We really wanna stress on references.

**Harry Stebbings** [14:13]:

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, not where did they fall down that you should have seen?

**Kyle Norton** [14:26]:

So there were two scenarios like this. One, 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 trying to build something generational, you actually do need people that are gonna bring positivity, optimism, enthusiasm, so that 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. You will cut it that soon.

**Unknown** [14:58]:

Mhmm.

**Kyle Norton** [14:59]:

Wow. 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 couple 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 gonna be worse later.

**Harry Stebbings** [15:30]:

Can you help me? I join Owner. 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.

**Kyle Norton** [15:41]:

What

**Harry Stebbings** [15:41]:

have been your lessons on how to do that really well?

**Kyle Norton** [15:44]:

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 26 AEs and 30 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.

**Harry Stebbings** [16:07]:

How many in enablement?

**Kyle Norton** [16:08]:

Five total. Five in enable, and what's their core role? 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.

**Unknown** [16:23]:

Okay.

**Kyle Norton** [16:23]:

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 ten 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 Avara, which is 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 LiveFire reps with our sales enablement manager. 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 gets very, very practical. Then they graduate into the team.

**Harry Stebbings** [17:19]:

Sorry, I have so many questions. Just wanna break them down. 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?

**Kyle Norton** [17:30]:

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.

**Harry Stebbings** [18:03]:

Can we not just hire some monkeys if we just have everything? I mean it in the nicest way. Yeah. 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 multithread it. Fuck me, AI

**Kyle Norton** [18:15]:

can do that. 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 gonna tailor that in the demo now. And I know this is gonna be an issue and I wanna 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. 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.

**Harry Stebbings** [19:07]:

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

**Kyle Norton** [19:14]:

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.

**Harry Stebbings** [19:25]:

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

**Kyle Norton** [19:30]:

Yeah, it works, works for us. It works well? Yeah, I mean, the content I think is pretty interesting. It's gonna 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. So week two,

**Harry Stebbings** [19:49]:

they had to Canada.

**Unknown** [19:50]:

Mhmm.

**Harry Stebbings** [19:51]:

Okay. So are we fully in person?

**Kyle Norton** [19:54]:

No, 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 their job well.

**Harry Stebbings** [20:06]:

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

**Kyle Norton** [20:09]:

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

**Harry Stebbings** [20:13]:

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

**Kyle Norton** [20:15]:

thing. And of our recent cohorts, the two newest SDRs both broke the first month record for EMRR sourced. So what's EMR? Estimated monthly recurring revenue. Okay. 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.

**Harry Stebbings** [20:57]:

Yeah. No. I I listen. I totally agree. I think you need to be. Can I ask, what are the ACVs? I know with transaction, it's tough, but like blended. Like eight, nine k. A year?

**Kyle Norton** [21:06]:

Mhmm.

**Harry Stebbings** [21:07]:

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

**Kyle Norton** [21:12]:

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 BDRs spend 50% of their time doing nonsense, doing account research and finding leads, and filling out their CRM. Is that nonsense? 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. What do you use for lead research? 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. Previously, before we went on this mobile enrichment campaign, our call to decision maker connect, call to DMC was like 3%. So you'd to make a 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 corporate.

**Unknown** [22:36]:

Why is it so bad?

**Kyle Norton** [22:38]:

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%.

**Unknown** [22:49]:

How come?

**Kyle Norton** [22:50]:

Because we have mobile phone numbers for everybody. So you're calling somebody's cell phone. And so now BDR making a 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 nine ks ACV, the numbers start to really add up.

**Unknown** [23:09]:

Wow,

**Harry Stebbings** [23:10]:

that's fascinating.

**Kyle Norton** [23:11]:

Yeah.

**Harry Stebbings** [23:11]:

What percent of converted sales are cold calls?

**Kyle Norton** [23:14]:

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

**Unknown** [23:20]:

90% inbound? Mhmm. Wow.

**Kyle Norton** [23:22]:

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 multichannel strategy in my opinion, so that as certain channels hit saturation or find challenges, you've got other places to go.

**Harry Stebbings** [23:55]:

When did you go multichannel? Because I think people can go too broad too soon.

**Kyle Norton** [23:59]:

Really early. We built an outbound team in q four of twenty twenty two, and I started in June, so pretty quickly.

**Harry Stebbings** [24:08]:

If you want to do an outbound team, well, I'm a founder, and I'm like, that girl, I need an outbound team.

**Kyle Norton** [24:12]:

Mhmm.

**Harry Stebbings** [24:13]:

What would you advise me?

**Kyle Norton** [24:14]:

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 lot of BDRs who are quite good that don't necessarily have that path to AE where they're at.

**Harry Stebbings** [24:31]:

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

**Kyle Norton** [24:37]:

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? Because that's hard. And if you have a great product and you bring that person into your environment, they'll do really, really well. We've hired a bunch of people, you know, that company where we've hired nine people from, that's a mediocre product in a very competitive market, 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.

**Harry Stebbings** [25:16]:

Okay. And so I just wanna go back. So we have 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 Dagnon, 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 volume Yeah. How does yours differ?

**Kyle Norton** [25:36]:

So in Chris's context, there will be so much pre call research and post call work and coordination and quarterbacking. Like I've sold enterprise before, so I think that makes sense. We aim to have roughly four demos booked per AE per day with three held. We know that there's gonna be some meeting.

**Harry Stebbings** [25:56]:

Three demos per day?

**Kyle Norton** [25:57]:

Every day,

**Harry Stebbings** [25:58]:

yeah. Wow, so they're gonna do 10 to 12 calls a day?

**Kyle Norton** [26:01]:

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.

**Harry Stebbings** [26:17]:

How many net new lead calls do you think your team have a week? Hundreds, for sure.

**Kyle Norton** [26:21]:

Yeah, because 26 account executives, they're probably But

**Harry Stebbings** [26:24]:

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

**Kyle Norton** [26:27]:

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

**Harry Stebbings** [26:30]:

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

**Kyle Norton** [26:34]:

Every You

**Harry Stebbings** [26:35]:

said they need to have three demos a day.

**Kyle Norton** [26:37]:

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

**Harry Stebbings** [26:40]:

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

**Kyle Norton** [26:46]:

35 ish today.

**Harry Stebbings** [26:47]:

So 35 book three net

**Kyle Norton** [26:49]:

new each, or Just call it two, call it two. Two each? Yeah.

**Harry Stebbings** [26:53]:

Wow.

**Kyle Norton** [26:54]:

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 higher intent. Should AEs be responsible for pipeline generation? In SMB, don't think so. In general, I think relying on account executives to prospect is probably a losing proposition. Why would you pay a $2.50 ks rep money to make cold calls when you could potentially have an 80 k BDR do that work for you, if they're good at it. I think account executives, especially mid market enterprise, have to do some prospecting, but it's not banging the phones.

**Harry Stebbings** [27:33]:

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

**Kyle Norton** [27:47]:

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 80 ks is awesome for them. And they have a path to one hundred and one hundred and fifty within two years, you're 22 years old. That's awesome. I don't necessarily think it's like a it's bad comp.

**Harry Stebbings** [28:12]:

How do you think about target setting with them? Mhmm. 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.

**Kyle Norton** [28:26]:

So our BDRs only get paid on Close One Business. Mhmm, 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 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. And that cost

**Harry Stebbings** [28:52]:

doesn't include transaction revenue.

**Kyle Norton** [28:54]:

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 quality deals, because there is a spread.

**Harry Stebbings** [29:16]:

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.

**Kyle Norton** [29:26]:

Not happening. You'll win some, you'll lose some. It all comes out in the wash. We feel really good about our economics and we know that when we changed comp to include eGBV, which means they are gonna be more focused on the higher value customers for the business, our estimated MRR on a per deal basis went up pretty What

**Harry Stebbings** [29:46]:

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

**Kyle Norton** [29:57]:

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. So what are you at? A good account executive like our inbound account executives close 250 k ARR every month. Wow. Mhmm. So it's a little different because we're not That signing means

**Harry Stebbings** [30:18]:

they basically close a client a day.

**Kyle Norton** [30:20]:

Yeah. Or more. More in a lot of cases. Wow. Efficiency. This is the thing. So when people talk about, well, you know, one of the things that surprises people is on the outbound side, we have two BDRs for every account executive. Oh, that makes no sense in SMB. Well, 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?

**Harry Stebbings** [30:53]:

Where do most revenue leaders misunderstand their P and L?

**Kyle Norton** [30:57]:

They don't even understand it. They don't know where to start. They think it's the domain of finance and finance gives them a headcount number and they say, you have 17 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, because 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? 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 4,000,000 in pipe and close it at a 25%, but our deal cycles one hundred and twenty days, you're cooked. There's no way to recover. You made that mistake six months ago. And so unless you really understand the model and are able to think both about today and delivering what's happening right now, and be thinking six and twelve months into the future, you really struggle.

**Harry Stebbings** [32:27]:

What channel has outperformed expectations, and what do you learn from that? Organic, probably. What do you think you did well to inspire organic to do so well?

**Kyle Norton** [32:37]:

I did nothing. That's never

**Harry Stebbings** [32:39]:

start with that.

**Kyle Norton** [32:40]:

Always

**Harry Stebbings** [32:40]:

it was me, it's the takeaway, but yes.

**Kyle Norton** [32:42]:

Yeah, this was a founder insight. This is Adam having an incredibly deep understanding of the customer in the market, and way before it made economic sense, he was all in on 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 gonna 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.

**Harry Stebbings** [33:18]:

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

**Kyle Norton** [33:26]:

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 twelve 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.

**Harry Stebbings** [34:07]:

Do you not think this is where marketing completely blends with sales though? Actually so many you have outbound, sure, but outbound is made far more successful when you outbound to someone who already watches your videos.

**Kyle Norton** [34:20]:

A 100%. This is something that a lot of folks get wrong is they like squabble over attribution. They're like, oh, this is sales

## Intro

**Kyle Norton** [34:26]:

generated, this is marketing generated, and you end up at these local maximas, and we have a sort of a strange org structure where our VP of marketing who owns brand and PMM and customer marketing roles directly into Adam, I own growth and demand gen, you would think like, oh, that's a little squirrely, and it works awesome. And everybody collaborates, and it's a really productive structure. And my growth leader doesn't worry about like organic attribution, neither does the VP of marketing. They understand that a ton of organic is actually driven by the paid marketing halo. So we don't worry about it. What channel has sucked when you thought it would be good? We just tried CTV and didn't have a ton of success with it. Connected TV. TV. So running pre roll ads on Amazon Prime or the like set top boxes.

**Harry Stebbings** [35:11]:

What do you think happened there?

**Kyle Norton** [35:12]:

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

**Harry Stebbings** [35:17]:

Was it expensive?

**Kyle Norton** [35:18]:

Wasn't that bad. That's the cost of experimenting, know, we're gonna 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 gotta think in bets, Andy Duke. The world is probabilistic, and some of these will work, and some of these will won't, and some of these won't, and we're gonna triple down on the winners. What are your sales cycles? A lot of one call closes, but average sales cycle's under a week.

**Harry Stebbings** [35:45]:

Under a week? Mhmm. How is that the case? I mean that with the most respectful, that is extraordinary. It's a compelling

**Kyle Norton** [35:52]:

product, that helps, and it's a burning platform for people. Like we are helping them make money, which is very important, so folks are willing to move on it. But something else we do that I think helps a ton, 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 call is, so I feature dump number one, which everybody tells you not to do, but I actually think people talk in such weird abstractions that customers don't understand. I'll be like, okay, we do five things, Website, online ordering, email, text message, marketing, custom branded app, listing management, all rolled into one. So that's like the product. But here's what you need to know about what's different than us and our competitors. We are gonna give you way less flexibility in customization. If that's your main priority, owner's probably not a good fit. But in exchange for sacrificing this flexibility, you're gonna 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 AB tests and the things that work, we're gonna roll out to every single customer. And we're not even gonna ask you some of the time, and you have to be comfortable with that. But in being comfortable with that, you now get an army of experts, legitimately the best restaurant marketers in the world and some of the best restaurant marketing technologists are working constantly on your behalf to do one thing and one thing only, which is make you money. You make more money, do way less work, but if you've got a custom font that you really love or you want videos everywhere and a spinning pizza sign at the top of the website, you have like really strong brand opinions, then it's not really gonna work. And so what happens is the wrong customers opt out immediately. 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 than 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.

**Harry Stebbings** [38:02]:

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

**Kyle Norton** [38:08]:

Some for sure.

**Harry Stebbings** [38:09]:

Really?

**Kyle Norton** [38:09]:

Yeah, And we have some larger brands, ten, twenty, 30 location brands now, many who have grown up on us. You know, we've helped them be so successful that they've franchised, they've opened a whole ton of locations. Do you have a constant internal battle of how far into enterprise you go? It's surprisingly easy because we're committed to the mission and we're committed to this product philosophy. We're not against working with a 30 location brand, but we are against working with a brand that wants high degrees of customization. More of those brands are gonna want more flexibility and choice and are gonna be are just gonna say, oh, actually this isn't the right fit. But you know, we closed a 33 location chain the other day and they came to us and they're like, yeah, I don't I don't wanna deal with all this stuff. I just want somebody else to figure it out for me. Okay, great.

**Harry Stebbings** [38:57]:

Here. But if you look at Olo, if we're blunt, why are they not a good business where you are? They're playing a different game.

**Kyle Norton** [39:04]:

They're playing a very different game.

**Unknown** [39:06]:

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

**Kyle Norton** [39:08]:

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.

**Harry Stebbings** [39:26]:

When you look at how you run your internal processes today, there's this 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 Owner?

**Kyle Norton** [39:42]:

So we don't do pipeline review. Okay. Why? We don't do deal review. Why? 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 gonna 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 gonna 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. Enterprise, obviously it does, and you're gonna do weekly scrutiny on every deal and stress testing it, but for us, I can understand everything I need about the business basically from Salesforce.

**Harry Stebbings** [40:26]:

What's your ramp time on new AEs? So

**Kyle Norton** [40:30]:

we've interestingly extended this recently. Why? We wanted AEs to start in the role better trained. We used to put people on the phones on day five, and now it's like day 11 or 12, because again, the deal doesn't matter unless it launches. And so if you are a new rep and you're saying a bunch of stuff that's like sort of not accurate, then you get into launch and they're like, wait, I didn't know about this and this and this, Then the trust is completely broken and oftentimes people will pull out again because we're contracting month to month.

**Harry Stebbings** [41:03]:

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.

**Kyle Norton** [41:22]:

There's still an opportunity 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.

**Harry Stebbings** [41:45]:

Do you do shadowing? Will sales leaders join calls for the first call, second call, third call? Oh,

**Kyle Norton** [41:50]:

yeah. Big time.

**Harry Stebbings** [41:51]:

Talk 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 ask too. How do you do that? When do you hand off?

**Kyle Norton** [42:03]:

The reps will go through the training, and then they do a bunch of the sales simulation, then mock calls, get certified on the craft, and then they do an operator certification, which is like, do you know 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 closed deals in that first couple of weeks.

**Harry Stebbings** [42:40]:

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 restaurants, are you really like jumping onto like sales demo calls from a plush office being like, oh, thank you, Kyle and Jessica. Lovely to see you. Are you like, hey, why are you bothering me?

**Kyle Norton** [42:58]:

Fuck off. 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 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. How important is it to go in person? Person.

**Harry Stebbings** [43:19]:

You don't do any in person? Mm-mm.

**Kyle Norton** [43:21]:

A la bobelle, why? The economics don't make sense. We're so efficient running the sales cycle digitally.

**Harry Stebbings** [43:28]:

I'm not being rude. If you go to like a highly dense metropolitan area, there not like 50 mom and pop shops in a square?

**Kyle Norton** [43:37]:

We are highly targeted. I mentioned that we have these two ML models, one that tells us the size of that potential restaurant, so like how much revenue they'll do, and we have this thing called an e win score. And so that's our estimated win rate.

**Harry Stebbings** [43:51]:

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

**Kyle Norton** [43:55]:

So we don't want little tiny restaurants that are just like scraping by and have no customer traction, because we charge a premium, we charge $500 a month.

**Harry Stebbings** [44:03]:

And you don't want churn, Yeah, obviously, exactly. So they're doing like 500 ks to 5,000,000.

**Kyle Norton** [44:08]:

Yeah, and so we know that there's certain GPV bands where churn starts to tick up, so we say, okay, like this is our minimum for this segment, and then we have this estimated win rate. So you could knock on 50 doors.

**Harry Stebbings** [44:22]:

Don't laugh, is the likelihood of closure greater in different cuisine types? So like, if your GPV is under $300 for Indian, but under $700 for Italian,

**Kyle Norton** [44:32]:

is

**Harry Stebbings** [44:32]:

it different in that way?

**Kyle Norton** [44:34]:

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

**Harry Stebbings** [44:36]:

It'd be fascinating to see that, oh, the Italians, they close under a million, but Chinese, they're better on 500 k.

**Kyle Norton** [44:41]:

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 in a lot of depth.

**Harry Stebbings** [44:53]:

Got you. Because you don't wanna spend a ton of resources if the churn's super high. Mhmm. Okay.

**Kyle Norton** [44:57]:

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.

**Harry Stebbings** [45:31]:

The 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? Mhmm. Which is like very systematized and very scientific. Yeah. It's fascinating. So we have that. With different stages of sales come different challenges. Mhmm. You guys scaled really fast. I mean, how fast did you scale to 10,000,000 in revenue? What were you at when you joined? Two and a half. You're at two and a half?

**Kyle Norton** [45:57]:

We're at like 40 today.

**Harry Stebbings** [45:58]:

Yeah. Fucking mess.

**Kyle Norton** [46:00]:

Under three years. Yeah. And we're actually growing faster today than we Three years

**Harry Stebbings** [46:05]:

to 40,000,000.

**Kyle Norton** [46:06]:

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. Does customer

**Harry Stebbings** [46:15]:

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?

**Kyle Norton** [46:28]:

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, RevOps, enablement, data and biz ops, these are for anybody else looking at it would think like these teams are way overweight for the size of team and 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 pretty tough to stop.

**Harry Stebbings** [47:10]:

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

**Kyle Norton** [47:15]:

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 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 the pre sales gets all of the investment and post sales doesn't, but a company that I know you know is Pavilion, and we were their first customer. Yeah, Marc and I worked together very closely at Shopify.

**Harry Stebbings** [48:08]:

I didn't know that.

**Kyle Norton** [48:09]:

I had dinner with him last night.

**Harry Stebbings** [48:10]:

You know we led that round? I do. Oh, wow. Mhmm. Fantastic. I should have known that.

**Kyle Norton** [48:16]:

I love him. He's so good. They're an awesome team. Yeah. I'm 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 GPV, higher retention. And again, that's now an automated flow, where they go through these campaigns of incentives, they do the right things, not just for us, but for them as businesses.

**Harry Stebbings** [48:42]:

How do you think about that? 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? Again, it goes back to

**Kyle Norton** [48:59]:

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

**Harry Stebbings** [49:58]:

It's quite cheap, isn't it? Like $500 a month, actually think about $6 a year. I'm with you, but for everything you get, feels pretty good. It's a pretty good deal. Yeah. And a bunch of these customers end up making But I'm thinking like the margins are not great then. Because if you've like a launch specialist doing all of that shit, making menus, domains, making sure site's up to quality for them, they're happy with color schemes and the fonts and

**Kyle Norton** [50:25]:

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

**Harry Stebbings** [50:28]:

How many launches?

**Kyle Norton** [50:30]:

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

**Harry Stebbings** [50:34]:

Are they comped on a launch They are,

**Kyle Norton** [50:37]:

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 and quality of those photos? What's the story we tell? Do we have connection to their Google's business profile? Have we done all the business listings work? Is the SEO done properly? All that stuff is again delivered programmatically.

**Harry Stebbings** [51:04]:

You said they're LatAm based. Talk to me about that. Are they internal resources? Okay, why LatAm based? Just like a pricing arbitrage?

**Kyle Norton** [51:12]:

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 BPO at an arm's length type thing. We've made them part of our team, they're How? That's really hard to do. 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 in 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 we interviewed hundreds and hundreds of people and found a system to basically identify good folks.

**Harry Stebbings** [51:57]:

How many do you have in LatAm?

**Kyle Norton** [51:59]:

70 people probably.

**Harry Stebbings** [52:00]:

Wow, how big is the company now?

**Kyle Norton** [52:02]:

Approaching two fifty.

**Harry Stebbings** [52:03]:

Fuck.

**Kyle Norton** [52:04]:

What

**Harry Stebbings** [52:05]:

breaks with scale?

**Kyle Norton** [52:06]:

Everything. Yeah. I think one of the things that I am most hyper paranoid of is the quality of leadership breaking. Because I think once, 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 arm's reach of every person in the org, and now there's multiple layers between me and any IC.

**Harry Stebbings** [52:32]:

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?

**Kyle Norton** [52:42]:

Well, I still get on demos almost every week. You do? 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 gonna prioritize. And I ran ran a bunch of these calls and the reps are like, oh, like you said this and this, like, I'm gonna 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 just do them myself. So I'm pretty intentional about staying connected. My BDR manager, Rips, dials himself. The AE director runs demos still. The new manager who started is gonna be like an AE basically his first thirty days and get like very, very close to the customer.

**Harry Stebbings** [53:32]:

What bit of the machine keeps you up at night? Talent acquisition. Yeah. Because it's really hard. It's real As specific as possible, I'm so sorry, but is it BDR acquisition? Is it launch specialist acquisition?

**Kyle Norton** [53:44]:

It's the speed at which the number is growing in every single role, because at some point, my content engine, like basically me cranking LinkedIn, will only get us so far, and so we need new channels, and I'm trying to make sure that we have these new sourcing channels lit up before we hit a point where it's like, oh man, we we 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, again, like, it comes back to this theme of how can you hit today, but also think about tomorrow.

**Harry Stebbings** [54:32]:

We're both fans of Jason Lemkin. Jason always just tells me, listen, young people just don't wanna work today like they used They just don't wanna work. Does that chime true with your perspective?

**Kyle Norton** [54:43]:

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

**Harry Stebbings** [54:57]:

Do you think wraps are coin operated? No,

**Kyle Norton** [55:00]:

no, I think it's always a mixture of incentives. It's too binary to say like, oh, they're either money motivated or they're mission motivated. I think a lot of people are really excited about our mission cause 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.

**Harry Stebbings** [55:17]:

If I came to you and said, I didn't give a shit about the mission, just being honest. I care about making money, and I'm gonna crush quota, and I'm gonna be here night and day crushing quota. Makes me nervous. Does it?

**Kyle Norton** [55:29]:

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

**Harry Stebbings** [55:33]:

Is that not okay

**Kyle Norton** [55:33]:

if I crush quota for you for two years? 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 see us and they go, I just need to seed my team with people from that organization. Yeah, they're gonna try to overpay, but if that individual believes in the mission and we're doing the other parts of that engagement methodology, so I have this methodology called cramps. So there's like five things I wanna 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. 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 onto them constantly and getting people to do their job as a just push, push, push, push, push, push, then you take away their internal locus of control, and they actually will become less motivated. So I wanna 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. 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.

**Harry Stebbings** [57:27]:

You're scaling into a new phase of sales leadership for you. Mhmm. What are you nervous about as you scale yourself as a sales leader? That's a really good question. I'm a podcaster. Mhmm. A good one at that. I go on dates and girls are like, that's a that's a really good question. I'm like, I have had practice.

**Kyle Norton** [57:47]:

I had an old boss who used to say, pay you to 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 gonna have the recruitment engine? Are we gonna be able to continue to source deals? I'm sort of scared of it all, and that is like a really positive motivation. What did you do that you wish you hadn't done? We haven't had as much success hiring senior reps, like reps with a whole bunch of experience. We've actually had more success hiring people in like a two to four year experience range.

**Harry Stebbings** [58:23]:

Jason Lemkin would say they know how hard it is, and they don't wanna 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 wanna do it again. True or not true?

**Kyle Norton** [58:34]:

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 gonna give you a lot of coaching and a lot of feedback, and we want you executing on our systems.

**Harry Stebbings** [58:46]:

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

**Kyle Norton** [58:51]:

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

**Harry Stebbings** [58:56]:

You know when your wife says, do you know, of course you can go out with the boys, it's your choice if you choose to leave me at home? That's that's kind of the same thing.

**Kyle Norton** [59:03]:

Maybe.

**Harry Stebbings** [59:03]:

Yeah. Like, oh, I think I'll stay in actually. Yeah.

**Kyle Norton** [59:07]:

So I think more senior reps come in and like, I know how to do this. I'm good. I'm gonna do it my way that's worked for me for a whole bunch of time. And oftentimes they can't outdo our system. Even though they have more experience and a more developed 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 gonna get coached every single week. Every month, you get a monthly report card that talks about what you did well and what the areas of development, and then you develop your secret sauce, like what are we gonna do for the next thirty 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.

**Harry Stebbings** [60:15]:

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

**Kyle Norton** [60:21]:

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

**Harry Stebbings** [60:51]:

And she sound like a riot on a Friday night. Actually Remind me to reserve my calendar. Sorry, dude.

**Kyle Norton** [61:00]:

I actually vibe coded in an app on a Friday night a couple couple weeks ago, so you're not wrong. Stebbings case. So I had her on my podcast, she was talking about her initiative, 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, 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,

**Harry Stebbings** [61:38]:

Respectfully, Why do you need custom AI versus off shelf AI application? Could be off shelf.

**Kyle Norton** [61:44]:

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 our RevOps team to all get really conversant with GTM AI, and we're starting to get there, but I just want somebody dedicated to go absolutely all out on it.

**Unknown** [62:06]:

Wow. What

**Harry Stebbings** [62:08]:

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

**Kyle Norton** [62:11]:

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 flushed down the toilet with work that a data ops team should be doing for them.

**Harry Stebbings** [62:29]:

Does outbound become less valuable in a world of infinite supply? What I mean by that is I can just bluntly send 10,000 emails in a minute with AI outbound email systems. And we've got AI SDR tools. I mean, I'm laughing with the team's sake because obviously I'm an investor for a living too. I think we've seen 15 AI SDRs in a week. That's just what we've

**Kyle Norton** [62:52]:

seen in a week. You see these massive trends and ultimately that advantage gets competed away. Same thing with sales engagement. I was one of the first customers of SalesLoft Cadence. At that time, you could just have every BDR sending a 100 emails a day. The BDR team that I inherited at Vision Critical 5x 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.

**Unknown** [63:27]:

God, Aaron Ross.

**Kyle Norton** [63:28]:

Oh,

**Unknown** [63:28]:

yeah. Fuck me, that takes me back. Mhmm.

**Kyle Norton** [63:31]:

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 tremendous advantage with some of this generative AI outbound. It will get competed away and

**Harry Stebbings** [63:50]:

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. Interview the partners at the largest patent law firms and talk about their challenges, how they think about the future, dah dah dah. Don't sell the company at all. And then after the show, they'll be like, so what an owner do? Yeah. And you're like, oh, sure. Let me tell you for five minutes. You do one a week, you've got 52 leads a year.

**Kyle Norton** [64:21]:

I met a guy who generates 60 something percent of his company's funnel this way. They have five podcasts, this company. And all they do is interview the biggest names in their industry, and that person almost always introduce them to the person they actually wanna talk to, and then that person posts the episode on their podcast, and.

**Harry Stebbings** [64:41]:

I'm on Owner's The Manual podcast, and I'm so excited. And then all of the competitors are like, oh my god. What the fuck is that?

**Kyle Norton** [64:49]:

It's a great strategy.

**Harry Stebbings** [64:50]:

But but it's so underutilized. And it's actually underutilized because the cost of entry is still quite high versus posting on LinkedIn. Mhmm. You have to get Riverside, you have to get a microphone, you have to get the gas Yeah. Versus tweeting or blogging or doing any of that shit. It's still quite hard.

**Kyle Norton** [65:05]:

But even that is a a nothing investment. What's what's a podcast? Like, 200 and something bucks and

**Harry Stebbings** [65:11]:

I have no idea, but not much. No. I

**Kyle Norton** [65:13]:

completely agree with you. My entire home studio setup was like $2.

**Harry Stebbings** [65:16]:

I completely agree with you, but people are lazy. They are. And it's still much harder than posting on LinkedIn. Yeah. You're not wrong. And my favorite thing about secrets is you tell the world and people still don't listen.

**Kyle Norton** [65:30]:

Do you know what I mean? 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 Stebbings, like execution is the only moat, and I'll always execute, out execute these folks. Yeah. I'm a 100% confident in that. And the other piece is like, if you're a direct competitor of mine, and you start using my tactics, I'm in your head. You know now that I'm better than you are, and you'll have to carry that with you, always knowing that you're one step behind, and you're just trying to copy me.

**Harry Stebbings** [66:08]:

My my mother, actually, I walk with her every weekend at 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, because I'm telling them that I'm making spaghetti bolognese. Mhmm. 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 mixed in 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. Yeah. 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 don'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.

**Kyle Norton** [66:52]:

Yeah.

**Harry Stebbings** [66:52]:

It's how you do what you do.

**Kyle Norton** [66:53]:

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 the whole piece.

**Harry Stebbings** [67:27]:

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? We don't that much. Yeah,

**Kyle Norton** [67:36]:

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. 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 three x, and they're making like $6 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 a hundred hours a week and net net net net, you're only making $80, and now there's an extra $40 in your pocket because we've helped you grow online, which is highly profitable. It's easy to be really excited about that. We do pay attention to some competitors, but we're running Which

**Harry Stebbings** [68:19]:

competitor do you most respect?

**Kyle Norton** [68:21]:

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 are 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 trying to leave your your That's

**Harry Stebbings** [68:53]:

really inexcusable, especially when it's like mom and pop shops who are vulnerable

**Kyle Norton** [68:56]:

and don't have the power. That makes me mad. I know that in the long run, we will win because of that. You know, in the short term, I'm sure it's helped them hold onto some deals and stem some churn here and there, but none of those customers feel good about that relationship, 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 optimize for the long term. Like why don't we lock customers into year long contracts? We probably could. Well, we wanna earn your business every single month. Does that lead to some short term churn? Yeah. Does it put tremendous pressure on us on product and execution to deliver an amazing customer outcome? Yeah, and I think long term that compounds and becomes a durable advantage. Like we part ways really nicely with people. If you wanna leave Owner, we'll actually help you move on to your next thing. You wanna 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.

**Harry Stebbings** [70:06]:

Dude, I wanna move into a quick fart. Can talk to you all day. You are advising a 23 year old. I'm your little brother. Okay? And I'm 23, and I've got my first job in sales. I'm a rep. What do you advise me, knowing all that you know now, entering this workforce?

**Kyle Norton** [70:22]:

Mhmm. Focus on the inputs and not the outputs. Focus on your work ethic, your rate of learning, your coachability, learn consistency every day, daily discipline, and know that the outcomes will eventually come.

**Harry Stebbings** [70:37]:

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?

**Kyle Norton** [70:45]:

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 12:15AM Toronto time, and the West Coast reps closed deals even later than that. It was just a really cool moment because we knew it was an important month for the company. And even at 10:30, 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.

**Harry Stebbings** [71:49]:

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, I think they'll be a $2,000,000,000,000 company. I questioned actually that in the early days.

**Kyle Norton** [72:01]:

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 three and I updated a bunch of my like chat GPT workflows to use three, and I was just like, holy crap, this is so different. The memory, the reasoning, like the speed and being able to do research, and also deeply reason, it made me think that this roadmap is moving even faster than I anticipated. You can take Jason's

**Harry Stebbings** [72:40]:

side or Rory's side on who is right. Is AI gonna bring mass unemployment in a way that we haven't seen before?

**Kyle Norton** [72:49]:

I don't think so because of Jevan's paradox. You saw this argument as compute got cheap, well, all these foundation models gonna be less valuable. It's like, 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 gonna want way way more of those? I think yes, and I think AI is gonna 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 Jevan's paradox may lead to high employment.

**Harry Stebbings** [73:32]:

How do you motivate sales teams when numbers are missed?

**Kyle Norton** [73:36]:

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

**Harry Stebbings** [74:32]:

Tell me, Owner, 203510 out, where is Owner then?

**Kyle Norton** [74:37]:

I think we'll be a generational public company. The only reason I left Shopify, because I loved my setup there. I still love Shopify, I think it's an amazing company. I think Toby is one of the greats. There was nothing making me wanna 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 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 wanna be one of the handful of people that have taken a company from early to IPO, You need an incredible team in market and all this stuff to be able to make that happen, and I thought Owner was that bet, and I actually feel more bullish today on that than I did three years ago.

**Harry Stebbings** [75:21]:

Dude, I have loved this. I so appreciate you sending over your thoughts. So we obviously have our research. I'm very glad that I bluntly freestyled most of the time. It's so much nicer, but you've been amazing, so thank you so much.

**Kyle Norton** [75:33]:

This was awesome. I really appreciate the invite. This was like a career bucket list thing for me. Know, I've been a fan and a listener of yours forever, so this was a blast. I

**Harry Stebbings** [75:43]:

mean, that was such a special show to do. It makes such a difference being in person. We have so many incredible founders reach out and post shows like this, and say how they change their organizations because of shows like this. Let me know what you think. You can email me Harry@20vc.com. But before we leave you today,

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