So, you just said two things that I think are super important, and the theme of the opener yesterday was tough love. So, I'm going to make a tough love statement because what you just said I think is so important is that you as the CRO are in the tools every day and you're super interested in it. You're genuinely curious. If your sales leader that you're thinking of hiring, especially that you have, is not in the tools and worse, not curious, are they going to make it today? You're cooked. You're cooked. You're cooked, right?
Hey, are you tired of listening to hours and hours of sales calls? Recording is yesterday's game, folks. Yesterday's game. Attention.com unleashes an army of AI sales agents that auto-update your CRM, build custom sales decks, spot cross-sell signals, and score calls even before the coffee is cold. Even before the coffee is cold. Teams like BambooHR and Scale AI already automate their sales and RevOps using customer conversations. Step into the future at attention.com/saasstr.
Thank you to the early bird. Very kind. Day three. Somehow by day three, 9:00 becomes very early. Kyle, thanks for coming. Thanks for having me. A little background, maybe a month and a half ago, we do a SaaStr Workshop Wednesday where we do a live meetup. I did a version of this AI and how sales is changing a month ago, and I went to redo it, and so much has changed in one month.
So, I want to talk through where I think it's going to happen. And then Kyle is here. If you followed SaaS, you've probably seen Kyle before. He is the CRO of Owner, which just raised at a billion dollar valuation the other day. This week, Tuesday, you announced it just for SaaS. Tuesday. Tuesday. A billion dollar valuation. So, congratulations to Kyle. But even better, Kyle was close to the first meeting, and you were not the first person in sales, but you probably joined around a million-ish of revenue, right? Two and a half. Two. And in fact, he joined incredible founders. You can watch all the stuff on SaaStr, but maybe even while the company was in transition, right? Your first couple months might not have even been the easiest, the smoothest ones, right? And several stages. So, pretty impressive. And I've watched Kyle do something. Two things that are germane to this conversation. One is they're doing SMB sales to tiny restaurants that do not read email, okay? That do not do this. The ACV is higher than you might think. It's approaching 10K. But this is a hard sale, okay? It's a full high four figure sale to tiny business and vertical SaaS that do not buy software, that are not looking for things to bolt on to Salesforce or HubSpot, that probably don't give a crap what CRM is, right? And Kyle has crushed it in general. So, we could do a whole section on the secrets, but then Kyle is just very curious about sales. He's a student of sales. And so whatever AI is today in sales, but it'll be more interesting where it's going to be the next. I couldn't think of someone better to join the conversation. So is that a good bit of background?
Yeah, we're trying to put AI in everywhere we can, and I've mandated to my team that this has to be a mission critical priority. So I'm thinking a lot about it everywhere, and I want—I've got a bunch of stuff I want to talk about.
But when you said mandate for your team, because this is a question we got even to Yamin yesterday, what does that mean? How do you show the team the path forward for AI in sales?
It has to start with you as a leader. I'm in these tools constantly. I'm definitely the most well-versed in this area of the business. And I think I find a genuine curiosity. I'm interested in it. And also, like, I have such high conviction that this is going to be the most important thing that we can figure out in the next 12 to 24 months. And so anything that I'm doing, I'm putting into our leadership channels, my personal Clay workflows or the ChatGPT projects like that I use individually for me as a leader. And I take a lot of demos. I talk to a lot of founders. I listen to a lot of content to try to stay on the cutting edge with it because, like you said, it's changed radically in 30, 60, 90 days. And the risk-reward is so big that it takes up a lot of my mind share.
So you just said two things that I think are super important, and the theme of the opener yesterday was tough love. So I'm going to make a tough love statement because what you just said I think is so important is that you as the CRO are in the tools every day and you're super interested in it. You're genuinely curious. If your sales leader that you're thinking of hiring, especially that you have, is not in the tools and worse, not curious, are they going to make it today? You're cooked. You're cooked. You're cooked, right?
Yeah, because the competitive pressure is so great. If you are not making this a mission critical priority, your competitor is. And if you look at the gap in productivity between us and our main competitors, it's so drastic. I can spend so much more money on a per person basis than anybody else we compete with in marketing, in post-sales, because our machine is anywhere between three and four times more efficient on a per rep basis.
Yeah, I want to come back to that. 1.5x, 3 to 4x is pretty big. I want to come back to that, but you're cooked, right? I genuinely think, and that if anyone on your executive team or honestly, I know this is tough love, anyone on your team that by June 30 is not deeply curious, like is not pretending to use ChatGPT once a week to get recipes, your team should be both scared and a kid in a candy store. A kid in a candy store. If your team is not, this is effing cool, right? Every week I use a new tool, right? And I was slow. I for—and I want to talk about this. I was into AI as a student, but until we launched our SaaS again, I said we had 130,000 chats in 8 weeks, then I've got it. And now I use—I mean, I was using, but now I use brand new tools every day. Like all the little videos I made, I use this app called Hicksfield AI, which is super cool. Like a lot of the design, this was done on AI. Our design, we have the best designer in the world, but this whole idea was done in Revid.ai. So if you don't see these people, if they're not talking in the hallways and talking in the weekends and on Slack about this cool what you can do in AI and GTM, I think at least I give them till June 30. By June 30, if not, if July 1, I would like just start taking—I know it's mean, but start taking the black pen to the org chart because they had their chance, right? They had their chance.
And I've already done this from a hiring perspective. Anybody in leadership. So in any leadership role, there's a component of the interview that's now, what are you doing with AI? What do you know about it? How are you using it today? And I really want to unpack it, and it's been a mandate. I don't care how good this person is, if they're not in the tools and what I consider to be AI native, like we can't hire them. And I have a half-drafted Toby-esque letter for my team.
Yeah. Toby from Shopify who wrote a letter to all of Shopify about how everybody needs to be AI native. I've drafted the same thing for my management team. And again, but it can't be superficial. Like, you might not have to get here, but like I'm in Windsurf vibe coding my own apps for internal use as a CRO. Yeah. As a non—I don't know, you told engineer as a kid? No. Okay, you're in Windsurf.
I took one Python course in early 2023 when ChatGPT was blowing up just to learn a little bit about it. But now with Windsurf, I can legitimately—so I've got my GitHub repos and I've got it all set up so that I can actually do what I want to do. And so I'm pulling stuff out of the Lever API to run analysis on how we're hiring. Like I can do—you can do so much more if you put your mind to it. And that maybe you don't need to get to that bar right away, but it can't be recipes and ChatGPT. That doesn't qualify.
And so when you're interviewing an AE or an SDR today—and remind me the ratio of like general outbound to inbound at Owner—but when you're interviewing for either role, what's a good answer to that question? What's a good answer to the interview?
I'm not actually as concerned for ICs. Yeah. Because we are running an SMB motion and so most of the automation and AI is centralized. It's in my BizOps and RevOps team. I'm now hiring for a GTM AI lead. So somebody who will do nothing but this within the RevOps organization. And so I don't actually need the reps in a bunch of tools messing around.
Okay. But do they need to be AI curious?
I think long-term they should, but for what I need them to do, I don't actually care because we're doing—so if you were an enterprise rep, absolutely. But for me, I'm going to do the AI call prep and sell between work and the CRM enrichment. I'm going to do that en masse for everybody on their behalf. Okay? I'm hiring one to three-year tenure reps on the upslope of their career. And I don't need them to be recreating the system. They need to operate within my system and execute the methodology, but for the betterment of their career prospects, yeah, they should be trying to learn it themselves.
It's just funny. I think that makes sense to me. And I want to ask you then, what stack do they walk into today? What's this? And are they more efficient? But it's interesting if you're hiring folks with two to three years of experience, right? They could be any age, but let's say they're 24 on average, right? I wonder if the ones you hire in two to three—that's going to be okay. Two to three more years. The kids today that are graduating high school or college, if they're not AI fluent. Yeah. Even in sales. Yeah. I don't know, man.
Yeah. And we talk—I talk about it a lot across the team. So I do hope to seed that curiosity. It's not as much of a mission critical thing. But if you're a manager and you don't have a high degree of proficiency to just default to AI automatically for any problem you're solving, then it's really difficult to think that person is going to scale with the company.
All right. Okay. So help us then. Let's be tactical about it. I walk into Owner. I'm a new AE with three years of experience. What do I walk into? And does that mean I can do more meetings, more calls, more outreach, more texts? Like how does that—what do I walk into and how does that 3 to—you said 3 to 4x. I believe you. You're very—you're not an exaggerator. That's a big 3 to 4x. So what do I walk into and how does—how does that output happen?
It's a very low bar for some of our competitors, I know, but so it's everything is on Salesforce is the foundation. Then on top of that, we use Momentum for automated CRM enrichment. And you can basically do whatever you want with Momentum. It can look at call transcripts, run custom prompts, fill in the Salesforce field, run an automation, ping somebody in Slack. You said the wrong thing on a deal, something that we know is the wrong expectation, that'll go to the manager and the rep and be like, Jason said this thing, yeah, we don't do that, so that they can correct it before the deal closes. So Momentum is the foundation for a bunch of our—a bunch of our automation, and that's been a big focus. Automate everything. Like what is in the rep's way of being on sales calls and following up and generating revenue every single minute of the day.
Yeah. And so we've gone from—we've—we're probably up 25 to 30% in terms of the revenue generating activity time because they don't have to fill out CRM after. They don't have to update the notes for the launch team. It's all done. It's all done for them.
That's—is that a—it's a classic KPI. Is that a top KPI getting that above 30% time in deals?
I would like the RGA time to be like 70, 80%.
70, 80%. We've gotten them 25 to 30% more revenue generating activity time. And how many—I remember back in the day when Brex was taking off and Sam was really into efficiency pre-AI. Goal was at least four. Four to be—automation state of 2021 was the rep would walk in with four, four appointments on their calendar for them. What is—what's the version of that today?
So for us it's four demos. Four demos a day.
Three. He—I think Sam talks about it. Four meetings of any type. We're trying to get to four demos. Three held because it's SMB. So there's a no-show rate. And then probably two follow-ups and then a healthy amount of white space where they're calling open opportunities. They're doing a little bit of pipeline generation, but actually not much on the AE side.
Yep. And then the call prep, call follow-up, CRM, handoff stuff is at a minimum. So let's talk about AI and follow-up. You probably didn't see it, but I tweeted this and I told this story of this and I wrote a SaaStr post on great AI outreach, terrible follow-up.
Did you see this one? I don't know if folks saw it. I don't want to repeat it, but like a week ago, I literally got the best outbound email ever. It's like for our podcast and video, like this session. They said, I'll take your session with Kyle. I'll make the world's best clips. I'll automate all the editing. I'll put it on iTunes and Spotify and YouTube for you. I'll do it all for you. It'll all be—I guarantee it will be better than what you're doing today. And it was like—and this is exact—and here are my clients just like SaaStr that will do it. And this is a week ago. So I'm literally like, I'm in. He's, you want to do a demo? I'm like, no. What is it? I'm like, I didn't care what it cost as they said as long as it's fair. I have no time. I'll buy today. So I was in. And then he sends a follow-up email. What is SaaStr doing and how many podcasts have you done? Yeah. Rough. Okay. Yeah. And then yesterday, I told the story. I'll tell the follow-up, but I want to hear your learn. Yesterday, I told the story before, but I didn't tell the follow-up. Yesterday morning, I got an email from a well-known B2B company. Hey, Jason, saw you'll be at SaaStr next week. Would you like to meet next week? Yeah. Hey, Jason, I know you might be busy. So many flaws in that. Yes, I might be busy. Two, this is the worst week to meet me of all the 50 weeks of the year, but next week. Okay. So then I email him back. Worst outbound ever. I wrote in all caps. I really can't believe because I just want to see. I'm not upset. I just want to see. And then the guy writes back, This is what happens with bad AI automation.
Yeah, I got one of these recently, too.
Did you get one of them, too? Maybe the same company.
So it's poor orchestration. I think this is when you have people trying to apply AI for the sake of it, but they're not thinking through customer journey, the entire thing.
But how do you do that at Owner? So Owner, like restaurants do not suffer fools. I have no time. No. And your product's expensive. Yeah. So how does that—how do you automate the follow-up?
So it's great. I have a great RevOps leader who is very fluent in sales and the actual go-to-market fundamentals. I think I see this mistake where you have RevOps people investigating tools and then applying them, but then there's no thought of, okay, how does this get to a rep? How do they follow up? How does the manager then look at what's going on? And so I'm in the process of building what I call the management intelligence layer, which is what is the always-on layer for the manager to understand what's happening on a rep-by-rep basis and get prompted when things are either off base or off track, and so that they can nudge the rep back into track, back onto what they should be doing. And so you have to think through, okay, there's AI tools, but then there's also how does the—how does the calendar of the manager look and how does that integrate with what they're trying to achieve? And so we spent 8 weeks at the beginning of the year redeploying what I call my like core operating methodology. And so we wiped every single meeting off of the calendar, started from a zero base and said, okay, what are the most important activities? Coaching is number one. Okay, let's plant the coaching into the manager's calendars. And then it's—there's like some audit mechanisms and then how do you make the audit mechanisms as efficient and effective as possible. And so we're starting from what does the business outcome need to look like and then layering in AI to accelerate all those things. Not saying, okay, I want to use AI for this thing and then trying to fit your business into it. And so I think it's really about being thoughtful about how you're orchestrating the entire business and then using AI as a leverage point as opposed to, oh, this AI thing's cool, so I'm going to slap it in.
Okay, let's go to the future a little bit before I—I need—I should know this quest—the answer to this question. I don't—what's our typical sales cycle at Owner and how many interactions on average does it take until you close a restaurant?
A lot of one-call closes. One-call closes, sub-7-day sales cycle.
And so the first touchpoint will be a BDR or an SDR following up. They book a meeting. They do a confirmation call and then demo happens. Lots of calls closed on that. If you're not closing a call in the demo, it's usually on that follow-up call. And if you're not getting them on that follow-up call, the win rate falls precipitously. And so it's almost not worth talking about what happens after that.
So the demo may be a good challenge to this little tweet I have. But I still want to—this is still what I think is going to happen a lot. I wrote this April 2024, AI can't beat a good sales rep. No way. It's dumb. It hallucinates. April 2025, maybe an okay rep, right? Yeah. And then April 2026, our AI is better than 80% of reps. I want to hear what you think about that. And then I pulled this. Clary just published this data. All—maybe you saw it too, right? I always knew this, but man, this is stark. Clary's—Clary I think was like a million opportunities or something. The top 10% of reps close 65% of deals. Yeah. I know you have a—a world-class team, but for these one-call closes, especially when the customer is more sophisticated—yours often isn't—but if I've tried Owner, maybe in a year when everyone has used Owner, do I really need a mediocre sales rep or can AI close that deal in a year?
We are augmenting reps with AI and not trying to replace as much. But we are building a PLG motion that will be heavily AI.
You're going deep on PLG, right?
Yeah. And we're in the process of launching our 1Mind Superhuman. So it's Amanda Kahlow's new business, founder of 6sense, and that will deliver a lot of the sales experience. So they'll answer questions on the website, build problem awareness, book meetings, answer a bunch of questions. And me as a buyer, I had a lot of conviction about this 1Mind investment because as a buyer, I was going to their Superhuman and asking a bunch of questions. How does it integrate? How does it do this? And I was like, okay, this will work. Yeah. And it's a question mark if our SMB restaurant buyer is going to be as interested in that experience as I was. But that will do a lot of the sales funnel. And so what I'm hoping to have is a part of the sales team that is really just order taking and they are doing 15, 25-minute, hey, I'm a human. Let me make you feel special. Answer a couple questions. Swipe a card. Swipe a card. I do believe that the Superhuman will take some portion of people all the way through the finish line, but we're also building a customer journey that is not AI and then human over here. I'm trying to build what I call semi-self-serve, which is a consistent customer journey that has different channels, different experience channels. You can come onto the website, talk to the Superhuman, you can talk to a rep, you can go through the product-led journey in the product where you've got your walkthrough and asynchronous demos. And what we want to build, because where I see people go wrong sometimes, is a way for a buyer to go through that journey, interact in the ways that they want and not get locked into this attribution problem or these silos where you're shipping the org chart and if you go through PLG and you don't buy, like there's no follow-up.
No, I want a sales—That's the worst. It should be—it should be an automated spectrum, right? You should get whatever version from PLG to handheld sales that I want—that the buyer wants. Shouldn't I?
Yeah. And people look at that, they go, oh, I'm going to pay a sales commission on this like PLG buyer. And I think it's the wrong way to look at it. I'm really trying to think holistically about the business, holistically about that customer journey and let people go back and forth, channel to channel, experience to experience, and we're just going to close them wherever we want. And so you could have a rep that is a recent BDR promote that is closing 50 deals in a month at a 9, 10K ACV because people are coming to them very warm.
Awesome economics. I don't need to squabble over—definitely you don't need to. Yeah. A related topic, but you—worst case you got to double pay for a while. The AI—you got to pay the human for the AI. Great. And anyone that's done a hybrid premium self-serve, this is not—this is pre-AI. You got to do it. If you get cheap on this, it creates too many conflicts. But it was interesting. Even though at first you're like, I don't—I don't know that an AI is going to close these deals 100%. But then you have PLG. So you already have a continuum. In a year or two, Owner will be deep into nine figures in revenue and you're going to get your second and third generation customers. They've already used Owner before. Yeah. And but they went to a—they went—they—that restaurant shut down or they got a new job. Yeah. They might not want to talk to a person. Especially if the product has a flexible contract, especially if it's a good deal. I already know. I got a couple questions, Kyle. Okay. I've moved to a new Mexican restaurant in Orange County. New point of sale. Do you—Yeah. Do you integrate with it? Do you integrate with—I got three questions. I'm in—I've already used it before and I don't—that AI might be better than—even on your team might be better than a human. So that—that it could be a material number of deals closing a year, couldn't it? With AI.
Yeah, it will. Right. Yeah.
And it gives your team leverage to do higher and higher value activities, go after bigger, more complex customers. The same thing with the onboarding team. We're really trying to onboard and leverage AI to automate a ton of what they do, but it's not to necessarily replace a whole ton of them. Although we will definitely slow the headcount growth in that organization, but there's so many high-leverage things that we could do with a customer in onboarding. Teach them how to use the product better, make sure that they're like really well enabled when they launch Owner, celebrate it with their customers and do a marketing campaign. We don't have the capacity to do some of that stuff now, but once you start to automate a ton of the more rote tasks that we do with people now, then you can move people to a higher-order activity.
I think—yeah, let me ask a specific question. Brian Halligan, who's better than me at every level, co-founder, but he said many times what he thinks is going to happen is AI is going to lead to more—less specialization in sales, more generalization. I think the opposite, and I—but I mean this specific because you're giving a really interesting background. I think what may happen with AI sales teams is you may just have a demo team. You can call them sales, but if the one thing you need a human and an Owner is that S-tier demo, maybe the AI does everything. It seamlessly grabs a person not next week when their calendar is free, but right now while they're on the phone. A human does whatever demo needs and then digital Jason can take over the rest if they want or I can, right? But you might have these interesting—you might have this human part of onboarding where you need a little bit of human—a human demo and then this human help me. I need more help than the AI. But then those might be like hyper-specialized rather than hyper-generalized.
I certainly lean here. This is—we get into this big debate about the full-cycle rep. I'm not into the full-cycle rep because I believe much more in specialization. I don't want to prospect. Cold calling is hard.
Unless it's their only job. It's—there's no chance they'll prospect, is it?
Exactly. And so I am a big believer in specialization. And similar to you, how do we think about where we apply the most expensive human capital to specific parts of the customer journey?
Yeah. But we'll see. One thing I just—and I want to ask you a follow-up on this before this one. One learning I had from you, I just hadn't thought about it this way. I think AI in sales, I have a slide later we probably won't get to, is going to lead to a big renaissance in self-serving PLG because if you want an AI to close a deal, it can't be a three-year contract arguing over discounts and terms. The AI has to be able to close it with zero friction, no games. Yeah. So I think that's going to happen. People argue—I don't think—but your point I think is even more thoughtful, which is that it may blur all the lines—the lines between self-serve, commercial, mid-market, maybe not deal size, but all the ways right now we have different teams interacting with different types of buyers and it's shitty for the buyer. Whether you're business—whether I'm a tiniest restaurant, midsize, I've got five restaurants, I'm bigger, it's just as Owner, just as important to me, it's a big deal. So why do I have to be segregated to some weird part? It's the game. Why shouldn't I have—why shouldn't all the experience be fluent whether I self-serve, little help, a lot of help? And so it may blur all these lines between the different categories, right?
I think so. Yeah, I'm very anti-attribution in general. Like I think we get into problems where we say, oh, this is a marketing-attributed sourced deal versus a sales-attributed one, end up making the local maxima decisions as opposed to saying, all right, how do we maximize this entire system and the credit. Let's not worry as much about the credit. And I think we're going to run into this because you'll have a growth team that reports into product that's doing all the AI stuff that's taking sales as deals. A CRO said this to me like a couple days ago. They were frustrated by like, what's your job here? Is it to hit your sales number or is it to build enterprise value? You should only be here if you're really doing this for a significant equity outcome. And so trying to get people's headspace around this like more holistic understanding of building a business is I think going to be really important because you're going to see this—you're going to see these silly silos where it's broken and things don't—aren't communicated across and we're trying to avoid that.
Yeah. I think it's a niche we'll see. I don't have any passion on this, but I think by the end of next year a point that everyone from Yamin Ranga and everyone's agreed is all through the dawn of time we've added better and better tooling. We added Salesloft and Outreach and Gong, but sales reps still close the same 3 to 5. They're closing 3 to 5 times their OTE. They're closing 500K, 4, 800, whatever. I think AI is not only going to boost that up, like your point. I actually think what's going to happen because of attribution is commissions are going to halve by the end of next year. Yeah. Because this is how the math's going to work. You're going to get credit for the—for—it's not just PLG. You're going to get credit for Kyle's AI closing the deal without you. Yeah. Okay. But if that doubles the output of your org inherently the—instead of whatever you take home 10% overall 15, it's going to be five, but you get everything whatever your patch is team. But I think commissions will have to halve as part of this.
Definitely. I think where there will be some pressure the other way is for the best sellers. If you have an elite mid-market and enterprise seller, they will have so much more leverage with all of these tools that the competitive dynamic will say it was—that seller was worth 350K to me before, but now look at what they're going to produce. Like I'll pay 500 grand for that person to pull them from somewhere else.
