How to build GTM Efficiency in SMB Sales Kyle Norton, CRO @ Owner.com

Yeah, that's gonna be fun. All right, some warm-up questions so we can get to know you a little bit better. Tell us more about your day-to-day role and kind of what you're up to right now.

So I'm the CRO of Owner.com. So we're a Series B vertical SaaS software business. We target mom-and-pop restaurants. So think of like your local pizza spot that you order from on Friday nights. That's our ICP. I run sales partnerships, customer onboarding, enablement, RevOps, and whatever else hangs on there. And been with the company about 2 years, so joined shortly after their Series A, and I'll talk more about our growth trajectory as a frame-up for the content when we get into the slides.

Great.

What project are you working on today that you're most excited about?

Lots. I get excited about the boring stuff. I just hired a really incredible VP of sales. And so improving the documentation and frameworks around how we want our frontline managers to operate is definitely something I've been thinking about for a long time. I spend as much of my time as I can coaching the frontline managers, but it's limited given how many other things are going on. So the thing I'm excited to partner with Brett on, our new VP, is building structures and frameworks and systems for the frontline managers to deliver the very best coaching and development for their sales reps. Great. What's up, Ray?

I was gonna say—

Hype man. Appreciate it.

We have your hype man is here. We've got people from Canada, from DC, San Francisco, Texas, Tennessee, Orange County. Someone prefers they'd be in Bali. Don't we all? Toronto, New York, Delaware, Singapore, Chicago, Dubai, Las Vegas. Gosh. I think we might have a new record with how many cities we're touching this week. So that's great. Atlanta, Toronto, Boston, Seattle, Paris, Portland. Amazing. Alright, Kyle, in the last 12 months, what has been the hardest thing that you've worked on?

Early churn. We're gonna talk a lot about that today. It is a huge needle mover when it comes to driving efficiency and unit economics. pre and post-sale. So we're gonna spend a lot of time talking about how we've reduced churn because it's been a massive focus.

Yeah, for sure.

And a hard one because you're balancing, you, you don't wanna sacrifice the sales number, but you wanna drive deal quality, handoff cleanliness. So we'll, we'll get into that a lot. Tunisia. Cool.

Great. Um, and then last question for you. What's your fav— your current favorite SaaS tool or platform that you're loving right now?

So I'll give a shout out to my friends at Momentum. So for those who remember Troops before it was bought by Salesforce, it's a little bit like Troops plus AI. So it, it sits in between Salesforce, your call records, and Slack. And so you, we use it to write custom prompts that run over call transcripts to enrich our CRM, to pull information out of unstructured call data and enrich our CRM in a structured manner. Triggers, notifications, easy updates. And they're just an awesome company to work with. They're earlier stage, like Series A stage company, but they ship product at a really fast rate. They listen to the feedback from the market. And I really like the founders, Ashley, Santi, and Moiz. And so they're, I think, my favorite of many favorite tools right now.

Current favorite. That's it in the moment.

Yeah.

All right, great. Well, Kyle, I'll pass it over to you. Just as a reminder for everyone, the session is being recorded. So if you do want to go back, refer to it, any tips or tricks that Kyle is sharing that you want captured, head to our YouTube page in the live tab. You'll see the recording there just after we close up. We'll also be posting the slides to SlideShare later today. So Kyle, thanks again. Go ahead, take it away.

All right. I'm going to share my screen. And just let me know when you can see it. Somebody, Amelia, do you want to give me a thumbs up? Caitlin? Thanks. All right. So we're going to talk about building efficiency and go-to-market. So a little bit about me. CRO at Owner. I've been in sales for 16 years, leadership for 15, tech for 10. This is my second early-stage startup. I joined around $3 million ARR at Owner. And previous to this, I ran a quarter billion dollar go-to-market unit at Shopify. So being in big companies, small companies, my first startup was enterprise. This is SMB. I believe in range à la David Epstein from his book called Range. So I like to do a little bit of everything from a learning and growth perspective. And so what I'm going to show, what I'm going to talk about today is some insights about how you can build better efficiency into your go-to-market motion. The title of the deck is about SMB. This isn't necessarily SMB-oriented only. I've run mid-market and enterprise teams. A lot of this content is very much applicable there, but we're going to do it through the lens of Owner, which is an SMB motion. And so there's 3 topics to focus on. So one is the importance of staying focused and how to say no. Two is we're going to get into ways to scale that don't include rampant inefficiency and burn. And then three, we're going to talk about how to build operational excellence into your organization at different stages in the growth curve. You obviously can't manage with the same rigor when you've got a small handful of reps and you're the CRO direct as the, as the manager. Versus later stage when you've got support teams and other layers of leadership. But we'll talk about that, that maturity, that maturity curve. And in terms of audience, so who I'm really speaking to here is founders and revenue leaders from companies that are post product market fit. So you're winning some non-Friends of Founder deals. There's some repeatability, but it's not a system, but you've got some patterns. You as the founder, the revenue leader, revenue exec, have some patterns that look like they're repeatable and you're just endeavoring to build that repeatability. Everything from that onwards to Series B, C, potentially beyond is applicable here. If you're still pre-product market fit, you've only won like a handful of deals and it's your buddies from YC, This is forward-looking, you know, never hurts to learn this stuff, but this is really the audience I'm targeting here. Okay, so a little bit about owner because this is gonna frame up the journey. I'm gonna try to keep this as real world and as practical as possible. So we're gonna talk about the owner journey. This also helps frame like why do I feel like I'm qualified to speak on this topic? In my opinion, it's because I've done it really wrong. I've made a bunch of the mistakes that I think we've all made over the last, you know, 4 to 6 years in this bull market, then ZIRP era. And now I'm starting to learn, I've learned some of those lessons and I've started to make some of the right decisions at Ownr. And so I joined in June '22, we went from $3 to $6 million in that sort of half year. We went $6 to $16 last year. We strung together a bunch of 10% month over month growth months. So we're, we've just broken through $21 million in ARR. In 22 months. So more importantly than that, so that's a bit of the growth story. We've done it while consistently improving productivity. We've reduced CAC pretty significantly and we've operated with a 1 or a sub-1 burn multiple, which is really where everybody's trying to get. Burn multiple is just for every, for every dollar of revenue you acquire, how much did that cost you? And if your burn multiple is 2, It takes you $2 to spend to acquire $1 revenue, not a super efficient business. If you're 0.5, very efficient, you could probably spend more money. So a little bit about the journey. I inherited this team with one manager, 4 reps, and early churn was a massive drag on efficiency. So it was definitely like a cleanup and a reboot job. I had to exit 2 of the 4 AEs within my first I think 45 days. Um, and we, we really needed to get our hands on, on early churn, which is gonna be the first topic I touch on. So that 2022 was a, just a foundation building year. We had to redo how we use Salesforce. We replatformed our sales acceleration tool, brought in some new, uh, infrastructure. It was foundation building. In 2023, we grew that team from 6 to 10 reps. So pretty modest growth. And we also built an SDR function. We, we started like a small SDR pilot at the end of '22. It was giving us good, good market feedback. And then we grew that function from 1 and 2 BDRs to a team of 10, then 12. And now we've got over 20 BDRs. And you're like, man, that's a lot of BDRs. That must be inefficient. It is not. And I will tell you how we've done it. And so we grew 2.5x last year while operating at an LTV/CAC of like 4.5 to 1. And the growth rate was actually better in Q4 2023 than it was in Q1. So more efficient, growing faster. And I'm going to walk you through sort of step by step how we got there. And then this year, the goal is to find the, find the outskirts of rep capacity. I keep thinking that we've, you know, hit the capacity of what a rep, an AE can handle, and they handle it really well. They keep crushing, the win rates stay pretty consistent. So this year is all about really finding how much more efficient we can make the AE team now that we've really nailed the demand gen, the demand gen playbook, especially on XDR. Okay, so now let's zoom back to '22. This is when I started. Now that you've got the story arc, things were not, not so peachy, but the product crushed with the right customers. There was a huge group of people using the platform who got tremendous value. We were shipping product fast, but the culprits for a very leaky revenue bucket were bad or like no targeting on prospects. We were closing a lot of poor fit customers. There was a lot of mis-set expectations from sales and the handoff was like sketchy at best. And so this led to fairly unsustainable levels of churn, of early churn. So within the first 90 days, we were losing way too many customers for us to feel like we wanted to put a bunch of money in the top of that funnel. And so the first lesson here is about learning to say no. And for us, it was about saying no to a lot of customers. So culprit number one was deal quality. And so we had a growth plan and I basically paused on it. I said, until we get churn in a, in a better place, I don't want to add a bunch of reps. I don't want to spend a bunch of money in marketing. Let's just dial in the economics and get to a sustainable place to feel like the machine was working before we added gas to it. And this is the exact mistake that I made 6 years prior when I was head of sales for my first startup. We got early signs that we were closing some deals and reps were now starting to figure things out. So we hired a whole bunch of reps we had way less figured out than we thought. Then we spent all this time hiring and ramping reps and we weren't spending that time on figuring out how to win with repeatable great economics. And so counterintuitively, trying to scale made us scale slower. And so saying no to growth is one of the important things and focusing on customer quality before you focus on jamming in as much quantity as you can. And a lot of this is, has to be data-oriented and I'll walk you through that. And so to give you a flavor for it, we said no to about 40% of prospects who we 15 days prior would have gladly closed one. So fun fact, my, the month I took over sales at Owner, we did less closed wins than the month before I arrived. And the month after that we did even less closed wins than that. And then I went into a board meeting the next month and felt really good. We had like cleaned up deal quality, the customer quality was way better. We started to see good signs. Jason M. Lemkin's on our board and who I've read and looked up to for a long, long time. And he just, he basically said to me, sounds great, none of it's showing up in your revenue number. So like, let me know when that happens. And like a bit of a terrifying moment for me as the new CRO. But it really reinforced that we had to find a fast path to making sure that the improvements we made on efficiency then showed up in the revenue number, which it did. And board meeting number 2 was a lot better. And so let's get into the data. So you got to figure out who to say no to. And a lot of that is it has to be data-oriented. And so I partnered with our Biz Ops team to understand what a high-quality deal looked like. So what were the, what was the digital footprint of a high-quality customer that then turned into high-quality revenue. And so the guy's name is Jonathan Shankman. He's a whiz. We could not do this without him. He figured out what a customer looked like from their digital profile and built a machine learning scoring mechanism called expected GMV. And that indicated based on, for us, it was like, their review quality, web traffic, their third-party marketplace volumes. We sell to restaurants, so how many orders they, how many reviews they get each month over month on a third party indicates order volume. And so we built a tool that then we could point at our ecosystem, our TAM of potential prospects. And you can see that highlighted on the right-hand side, that red, red and green chart there. So these are the different bands of expected EGMV, of expected gross merchandise volume. So you'll see when the volume is higher, the churn is green, it looks really great. You would dump money into an SMB business that has that profile. But smaller customers churned at a rate that we didn't like and we basically got rid of all those customers. But it made it so now we understood really carefully what made a good customer. We understood then the digital footprint of those customers so that we could go find them in demand gen marketing, in outbound, and we shifted 100% of our time and energy to those higher quality customers. And your sales team might not be super pumped. You're taking away a lot of ICP or a lot of TAM in quotes. And it's an education exercise. And then it's your job as revenue leader partnering with your data team, RevOps, or whoever to fill their funnels with high quality, high quality leads. And so this, so learning to say no is question number one. And I just, I generally say take on less segments, less customer types, less reps, just do less and just nail one small niche of a market before you hit the gas to scale. We always take on too much as revenue leaders. Like I think we're, and founders too, we're all optimists. Oh, like we can go, we're crushing an SMB, like let's do mid-market. We've got this restaurant, this like takeout restaurant customer, let's do it for dine-in restaurants. That's a lot of the time, maybe most of the time, like the wrong move. Staying focused for longer is a great way to nail your So now that we knew what that customer looked like, we want to be able to target them. So this is big takeaway number 2. Invest way earlier than you think in prospect data. And there's a few folks on the call that I've had individual conversations about this topic with, and I know how much of an impact it's made on their business. This is one of the biggest takeaways from today's session. Like spend the time figuring out, spend the time figuring out how you can equip your teams with really good prospect data because typically like a BDR, an outbound BDR wastes like half their time calling bad leads, like having to do research of their own to enrich the leads that they've been given. And we don't have our BDRs basically do any lead research. If they, if they get a lead and it's like partially filled out or doesn't have a mobile phone, mobile phone number, they just punt it back to the Garden of Eden and we resend that through our enrichment flow because you're basically saying to your BDR team like, hey, just work 2.5 days a week, that's okay. Like if you give them bad leads and it's that impactful. I did this analysis when I got my first head of BDR role at a software company that was enterprise and 40% of their time was basically wasted. I did the same analysis at Shopify, less because it was more inbound, but still lots of inefficiency. If you can get great prospect data, good things will happen. Essentially, if you go from like us, from 40% data accuracy because we sell to restaurants, super challenging data market, we went from 40% accuracy to 85% accuracy. Your BDR team overnight doing nothing else gets twice as efficient. We, our BDR team was unsustainably inefficient. We would not have scaled it, um, in its original iteration. We figured out the data thing, um, and now, uh, each BDR cranks out like over $80,000, over $60,000 in close one ARR every single month. Um, so, so highly, highly efficient. Um, and so you just have to, to triple-click on this data strategy. There's good providers out there now. You can hire somebody internally, hire somebody on contract. AI makes this way, way easier, but spend the time on this. And so we had a system where we took an entire restaurant database, pulled it into our Snowflake instance, ran a bunch of web scrapers and enrichment tools, filled in a bunch of the data that didn't exist. Then we would have, there was a confidence score on it to let us know if we think the data was accurate or not. Then we API'd into People Data Labs to pull a mobile phone record. And we did all of this stuff, which now we use a vendor for called DataLane, who's incredible. And I just can't stress how important this, this was. You like, it's, it don't bother hiring more than 1 or 2 BDRs until you figure out this data piece because it just, the economics won't make sense. And this is a picture of how that impacted connection rates. So the little red-purple bar on that top right chart is connect rates, and that's the connect rate of when we use this like upgraded enrichment flow. So we originally had a 3% call-to-connect rate. So a rep making 100 calls would talk to 3 prospects. Really tough to make that work from a, from a scale perspective. And now it's hovering around like 14 to 16% DM call to DMC, decision maker connect rate, you can definitely scale a team like that. So data is your superpower here. Spend the time on prospect data. It will make everything downstream better because if they're having more customer conversations, they get better faster. They put up better results. You build a culture of winning. The economics are good. It's, it's, I can't stress it enough. Okay. So we figured out what a good customer looks like. We found the digital footprint. We enriched our database like crazy to make our BDRs efficient. You can also feed some of that information to the ad platforms, less directly impactful but possible. Now let's fast forward to 2023 and we're, we feel like the economics of this base pilot team work and we want to scale. So how do we scale without rampant inefficiency sort of exploding? So going back to this topic of focus, less is more. We'll talk about the importance of single-threaded ownership. This is a slightly contrarian take, but something I believe in, and then we'll talk about infrastructure. So I've talked about this a little bit already. We made this mistake at my first startup. We had one rep closing a bunch of deals. We thought we figured it out, and then we hired a bunch of reps and it just like wasted our time, wasted our time hiring, wasted our time ramping, and we ended up having to lay off like 25% of that team and basically burned like 6 months. 6 months chasing our tails. And so I always, I say frequently to my team, to anybody who will listen, to founders I work with, slow is smooth and smooth is fast. Take on less, take on less and go deeper with it and you'll have more success. And this is one other point I'll say on this less is more thing, because I think it's one of the most common mistakes we make. You probably don't need as many reps as you think. The way that we, the way that we build our growth models, the financial model is the sell for the number of deals per quarter is always like reps times quota. And you're like, that's how many deals come out of it. But that's not really how a business works, or else you just keep dumping reps into it. Reps can— that math only works when there's the proper pipeline to make those reps successful. And so I would say like 80% of the time, companies that I work with have a pipeline problem and not a rep capacity problem. And in fact, if you just do the calendar test, this is something that Sam Blonde talks a lot about, who was an early EchoSign guy. So I'm assuming got it from Jason. But just look at your reps' calendars and if they don't have 3 or 4 customer-facing meetings on their calendar every single day of the week, you don't need more reps. And I bet if we all looked at our reps' calendars today, it'd be like 2, 1 to 3. You have a pipeline problem. It seems counterintuitive to have like double the number of BDRs to AEs, but the BDRs are half as expensive and you have a pipeline problem. So it's, in my opinion, better to just go spend the money on, on building more opportunity volume for your team than expanding rep headcount. This is a massively common mistake. You're also better to have less reps and pay more for them, in my opinion. Just like, get better reps. Take your budget, you had 6 allocated, only hire 4, give them more pipeline and hire better reps, pay a little bit higher in the market. I think that works out pretty nicely. We had this experience at Owner. We paid way above SMB market. I went and got to hire only top 5% Presidents Club performers from all over the place because they're like, wow, there's $30 grand more than I'm making today and everybody's hitting quota. This sounds like a sweet deal. It's expensive, expensive in quotes. But those reps are way more productive and way more impactful for a business than hiring more slightly less qualified reps. Alright, so topic number 2 under Scaling Smart. I think sales, I think single-threaded ownership is really smart for SaaS companies. You're seeing it more and more. And what I mean by this is having your sales leader own post-sales. And I could do probably like a 20-minute talk on just this, on just this issue. It's hard for sales leaders to think beyond the thing that they're targeted on and paid for. And so I've seen this multiple times in my own experience. When I inherit post-sales teams, I'm automatically way more interested in making sure those post-sales teams work really, those post-sales teams work really well. And I'm way more concerned about the quality of deals that go from sales to onboarding or launch. We made this decision in October 2023, and we saw an immediate improvement in deal quality, immediate improvement in rep responsiveness, collaboration. It really starts from the manager down. If you bring the managers into much closer contact, the AE managers and the launch managers, or if you're in a smaller company, all of those people being in one channel at the IC level, things just start to resolve themselves because you build a more human connection. And people inherently want to take care of each other. And this is a great way to drive that, to drive that shared, shared objective. This also makes the customer problem your sales leader's problem, which means there's no more finger-pointing. And I think that's really valuable. So I'm a big believer in, in single-threaded ownership, make your post-sales problems, your sales leader's problem somehow. Alright, I'm gonna move on from this topic. Alright, so now you've got the basics here, you've got the basics of economics that makes sense. You've got some replicability in your BDR motion or your pipe gen motion. Now you gotta get busy on infrastructure. And so the two goats in this picture refer to my director of RevOps and my director of enablement. They're sort of like the engine of our business. Steve, who runs RevOps, has been with me for like 8 years. This is our third stint together, which goes to show sort of like my reliance on him. And finding budget for this can be challenging because you're like, man, this is a big cost to layer on top of like only 4 reps. But you want to have these problems figured out before you hit the gas because those inefficiencies as you add reps just stack and stack and stack. So I encourage people to find creative ways to solve this problem. So for us, it was about hiring these two leaders on contract. So they were both from in my network. I could do it with a lot of trust and they started doing contract work with us like 10 hours a week, then 15, then 20 until the team was big enough and our ARR run rate was big enough to afford them. Without it sort of blowing up CAC. And I think this is a smart move. If you can find really high-quality fractional folks in this area, it will make a night and day difference on your team because you want to have a bunch of this stuff figured out before you hit the gas or else it just becomes chaos. And so the only takeaway here is like likely hire and invest in RevOps and enablement earlier than you think. Buy it off the shelf, find contract help, but try to find a way to do this would be my advice here. And these will be two of the most important hires you make for sure. Okay, so now we're gonna go into pillar number 3. We're fast forwarding to sort of late Q2 2023. We've built a bunch of these foundations, we've got some repeatability. We've got some good systems and technology in place. So now I want to talk about how to operate the team with slightly more scale with rigor. And so as your team gets bigger, and as there's more managers between you and the team, if you're the founder or the revenue leader, things are just going to start to like leak and break down. Because it's harder to communicate the feedback loop isn't, isn't as tight. So you need instruments in the business to make sure that things can move really smoothly. So there's 3 tools here that I'm going to talk about: the monthly business review, I'm going to advocate for very tight performance management, and I'm going to talk about my love for documentation. These are very boring topics and incredibly critical in my opinion. And don't need to be super complicated. And if you're taking advantage of these 3 things, like, you're really getting the Pareto principle of, of like the high-impact stuff, and then all the fancy operating rigor downstream of it is important. But if you can do these 3 things, you'll be in a pretty good spot. So this is like a screenshot of the MBR template. If you guys want this template, I'll publish it I'll just strip it out in our Notion and publish a copy for folks to use. Each team has a section, the manager, there's like a prompt in each section as you can see in the right-hand section that the managers of those teams fill out. And then the, the RevOps team is in charge of supplementing, of providing the data and charting for everybody to use. So this is a forcing function that happens every single month. It's within 4 days of the month closing, depending on when the month closes, to, to pause and think structurally about your business. It's really hard to get out of the weeds and view things from a, a wider scope unless you put this into your calendar. And so you spend a few hours on it thinking about operations strategy, like inspecting the data really closely, and everything gets more clear in my time. And the prep work is key here. So we're a remote company, and so asynchronous, we strive to be asynchronous in a lot, but I actually think this is a framework that works for all companies. So I'll give you like a little bit of a framework for prep. So one, you gotta have your template. You can use mine, you could use a slimmed-down version depending on your level of like size and sophistication, but just like decide as a group, what are the most important questions you want to answer every single month? What's churning and why is it churning? What's the rep performance and what's the, what's the stack rank look like? What are just like the key questions? And as you get bigger and the business is more complex, you will over time add more and more to this, but sitting down and agreeing to the framework is number one. Number two, RevOps populates this data for everybody. We try to have that done 2 days before the meeting. Then the leaders of each of those teams, first or second lines, will answer the questions that you framed out based on that framework and based on the information RevOps has published. Then everybody has like a 60— for me, it's a 90-minute block in the calendar before the MBR to review the deck and all the comments. So everybody goes in and reads every other section of this, of this MBR deck. It's a, it's a Notion page. And then people use comments to ask questions, talk about things that they see as opportunities. And then what we're talking about in the MBR meeting, because it's a very expensive meeting, you have a bunch of senior leaders, everybody has to get on one call. We only pull out the most important discussion topics. Do not read the deck in MBR. This is like the old way of doing it. RevOps builds a deck, they spend 60 minutes flipping through the deck, telling people things. You don't ingest the data as much as, as much as you should to make like, or to have thoughtful discussions in my opinion. So this pre-prep process where RevOps populated, managers answer questions, everybody reviews, then pull out the discussion topics. That flow will allow you to, to get a lot more insight. And it also makes it so that people who are not as brave or as extroverted in that synchronous meeting also have a chance to like provide thoughtful, thoughtful impact or thoughtful feedback because they're doing it asynchronously. And again, if you want the template, actually don't email me. I'll just, I'll just send it out. I was gonna say email me and I'll send it, but I'll just, I'll just do a public Notion page and you guys can grab it if you want. Okay. So now that we've got our MBR process, let's talk about performance management. This is another really important efficiency driver. So this is part of MBR. In MBR, every function gets a stack rank that looks something like this. It could be— this is like a simple version, but you could have your win rates, your close one attainment. You could have deal quality as a part of your AE framework. This is like an— this is an older one. It's a simple one. But it's important that you have the rhythm that you're— that you're looking at a stack rank consistently because especially as a small company, as any company, the cost of mediocre talent is very, very high. Especially in this market, because you're giving them valuable leads. Salespeople are very expensive. And so, and there's a cultural impact to letting mediocre performers hang around. So you have to maintain excellence in order to drive highly efficient growth. So you need to manage out bottom performers pretty consistently, even if they're doing okay. If people are only okay, but they show up in the bottom of your stack rank, you just got to move them out because the talent market is really good right now for startups. There's a lot of— there's less companies competing for talent, so you can probably go replace that person with somebody better. And for us, it's like the cost of entry to being a part of the owner team is excellence. The standard is the highest performance. So I encourage people to like pretty tightly performance manage. Um, it's uncomfortable to do, but you got to find the rigor, and doing it dispassionately in this MBR is a good way to do that. All right, last thing. I'm going way too long. Uh, so documentation. Documentation is sort of the pillar for scale. I love documentation. It's a great way to force really clear thinking for me as a revenue leader, and it also, uh, publishes all of this information so that people can get answers without a bunch of annoying slacks and questions and slowing people down. Great documentation will let you onboard folks way, way faster. It's really challenging to find the time to do this, but just force yourself to do it. Put in like a calendar block for an hour or 2 hours a week and just make this your documentation time. Could be how-to guides, a training framework, could be content that your reps can give to the market. The best, the only thing I'll mention here is my favorite hack that I used significantly before I had RevOps or before I had an enablement team and folks helping. I would do one-on-one trainings with reps and so like cold calling. So I would go through my cold calling framework. I had really crappy notes for it, flip through a couple slides and then I would take the recording of that training, I would pull out my part of the transcript. You can use any transcription tool, but pull out my part of the transcript, dump it into ChatGPT, and just say like, this is the recording from a training exercise, like turn it into a how-to document, turn it into a training guide. And your prompt can be that vague and it will still work. You'll have to do a cleanup But I can, I could produce content at probably like 2 to 4x the speed doing this. Because it's easy to talk and just like riff, especially as a salesperson, you're used to just like talking, talking, talking. So you can just riff, or I do this on my phone, like on the Peloton, I'll just riff on a topic, drop that transcript into ChatGPT, have it clean it up for me. And then that becomes a training, training page. Just find a way to document. Virtual assistants, like whatever, just, just document it all. It'll give you some, it'll give you scaling superpowers. All right. Those are the 3 pillars. One more bonus tip for the revenue leaders. If you want to make the leap to being like mediocre to great, you have to build P&L fluency. It's the like massive missing ingredient for revenue leaders today. You need to be able to focus and think outside of just your like close one number. And, and founders need to hire for it and coach it. And if your head of rev doesn't have this today, you got to find a way to give them exposure to it. Obviously, SaaStr has like a whackload of really good content on this. This is how I learned in my early days. Now there's way more courses out there that are great. Pavilion is the one that I send my folks to, Revenue Architecture School. Is like I have a manager of mine in it and he like knows how SaaS works now and he like really understands how this thing functions. So CRO school, revenue architecture school, Pavilion, I would highly recommend those courses. And if you're having frustrating conversations with your revenue leader and they don't get it, send them, send them down this path. They got to be P&L fluent. Okay, that is all I had for content. We learned about how to stay no, the power of focus, some lessons on scaling smart, the importance of data infrastructure, single, my opinions on single-threaded ownership, and some light frameworks to operating with excellence sort of on that growth curve. So I will take any and all questions now. I know that was a crapload of content, but Can I, can I steal one, Kyle?

It's Jason. Before we get—

Hey, Jason.

Hey, thanks for doing this.

Yeah, no problem.

Um, how in this— I mean, owner is doing well, it's well-funded, but we are, as you highlighted to us, we're in an era of more efficiency. So for someone that's even an outlier, how are you thinking? Are you thinking any differently about quotas, comp? What percent of the of how payment works? Let me step back. Maybe I'm rambling. Are you thinking any differently about sales rep compensation specifically in this environment than in the past? Any new insights or learnings on compensation?

Yeah. So I ratcheted back our sales comp over my sort of 22 months here. We just wanted to pay for the best talent we could upfront. You're dropping into like a very ambiguous, challenging market in an early stage startup. As you build more and more structure, comp should match sort of the complexity of that role. We've got scripts and playbooks and training and people you can learn from now, and the product is so proven. And so we're finding more efficiency by right-sizing comp. And there's a lot of comp— I haven't changed comp significantly in the last 6 or 9 months. but we're thinking about how do we tie the rep to the customer outcome more, tying them to the size of the customer through that scoring model I talked about, EGMV. The activation rate should probably be a part of that model. So yeah, I don't want to overcomplicate rep comp. That's not what I'm asking.

No, and maybe, maybe, maybe I think it's always a question everyone's fascinated with is comp, right? Yeah, maybe, maybe a different, a more strategic way to think about it is, and it goes to your earlier point about, and Sam Blonde's point about slightly fewer reps doing better, higher performing, right? Do you have higher expectations for attainment, for yield, for bookings per rep in the current world?

Do you—

I mean, Owner has a decent ACV, but it's still selling to SMBs, right? So in the old, old days, we kind of aimed for like 3x would be a nice place to skate to. In the old days, an SMB rep really didn't make much, right? Sometimes they still don't. And we'd hope they'd bring in 3x. Are you driving that up in any ways? Or how are you thinking about that, that metric in terms of the efficacy or attainment?

Yeah. So I mentioned in one of the first slides, 2024 is really about making the reps beg for mercy, is the joke that I say internally. So like, how, how far can we take rep capacity this year? And so we've been pretty modest in adding AEs while we've basically doubled the BDR team. And so I'm actually reworking our growth model as we speak based on new conversion rates and attainment and really trying to find the balance point. Like, it seems crazy to have 2 BDRs for every AE in an SMB business, but if your BDRs are generating 6 to 10 to 12 close-win deals cold every single month, because we figured out the data piece, it's a compelling product, then it's counterintuitive, it might feel weird, but that makes total sense.

Yeah, no, I want to lay another question. For what it's worth, I don't think it's unusual. I think some of it's market dependent, but actually some of it's the skill set of the sales team. I've— two for one, there was a moment, I'm dating myself, but you know, I don't know, there was a moment where outbound had its second coming, okay, maybe I don't know, 2016, 2015, early sales acceleration days. Yeah. And then actually a lot of folks did the 2-to-1 model because outbound seemed to work for everybody.

Mm-hmm.

Right. Outbound. And now, now you actually have to be quite good at it.

Yeah.

For the most part in 2024. But it wasn't unusual. And then I would talk to different leaders that were great like you and they— and some of them had none. Some of them it was like you would share an SDR, right? Yeah. But 2-to-1 may sound crazy, but I think if you're good, if you're truly good at outbound, right, which is harder today like you are, 2 to 1 is a great place to skate to.

Yeah, right.

Don't be scared if it's— if it works, don't be scared of it.

Yeah. And so we've more than doubled per month bookings, like aggregate per month bookings, and the size of the team has basically stayed constant. Yeah. And that's because rep productivity has increased through training and the enablement and then better, better pipeline going to them. We're trying to automate away as much of the rote sort of manual admin tasks now. I gave a shout out to Momentum earlier on the call. That's a tool we're using for it. So yeah, and in my model, the per rep attainment has gone up. The newly revised model, the per rep attainment's gone up in every single segment because we're seeing it's possible and we're seeing the reps get better and better and productivity keep growing. So I'm bullish on it. I don't know what the limits of capacity is. We have to find out. I thought I knew and the reps keep keeping up.

So, you know, if you really can get to a 2-call close or 1.5-call close and you have a high-energy team, you can be surprised what the ceiling is, right?

Yeah. Helps to have a good product and a compelling problem to solve.

Yeah. One last question, then I will, I will let other folks ask questions. But did you do this type of outbound at Shopify? Did you learn it on the fly at Owner? How did you get— let's, let's assume, let's stipulate you're good at it. Okay. But a lot of folks aren't. And a lot of founders and VP of sales, they're either, you know, there was a whole thread on LinkedIn this week about outbound not working right from Mark from Outreach, right?

One of 10,000 threads on outbound.

Yeah, it doesn't work. But, but, but I don't quite agree with that. And you don't agree with that either, but you don't disagree with it. How did you get good at it? Did you learn it? Did you screw it up at Owner for the first 12 months? Like, what's the learning? What's that process to get good at outbound?

We got good at it at League. That was probably the thing we did. So my first role in tech was in the software industry was to run global BDR for an enterprise company. And so we, I think I like 5x'd per BDR output because I eliminated all the like silly activity. We got super targeted on ICP. I rebuilt, I love, I come from a boiler room. So I think that's why I'm good at it. I come from—

Well, that's a good insight. You came from a boiler room, right?

Yeah, like my first job, I had a phone, a stack of paper leads, and a pitch book on my desk. And emailing was for bad words. Emailing's for like sissies. And so that's how I learned to sell. And so I think that's been with me and the super structured nature of that cold call, that boiler room. People don't like to be scripted. They're like, oh, I don't need to just like read off a script. I'm not some like phone monkey. It's like, no, scripting is awesome. Scripting is like the most powerful thing you could do. So just thinking about it, uh, hey Jeff. Yeah. Um, scripting is I think really critical and the more tightly you can get people onto like what we call golden script, the better they'll perform because then you can smartly A/B test, you know what's working, what's not. Um, do you think— learnable.

Yeah, that's the last question I'll have. I could spend the whole time on questions on this. I think it's, it's very interesting. Generally speaking, there's always exceptions. You started off in a boiler room, right? And I think so many revenue leaders I know that are good at outbound started off door to door in a boiler room with the Yellow Pages. Generally speaking, if founders are trying to make a bet, generally speaking, can you learn it late in life?

Learn outbound? Oh, that's a good question.

If you've, if you've grown up and you've been great at wherever, right? I would say primarily an inbound model. Can you learn it as your first VP of sales, a zero gig, or is it almost hopeless?

I wouldn't say hopeless, but I would say it's not very likely. If you want to run an outbound model and you've got a VP of sales who has been in 80% inbound models, it is because for them to, for that person to really grok outbound, you have to do it. And I know you've talked a lot about VPs of sales not wanting to get in front of customers and they're afraid to like go and pitch. I'm very strong agreement on that. And so like they're not gonna pick up the phone and make cold calls. They're not gonna figure it out themselves. So I never say never, but I just hired a VP of sales whose first job was door knocking selling solar at Tesla Solar City. So I'm—

I like those ones.

I'm a believer.

Yeah.

Yeah. You'll like Brett. Alright.

Let's some other questions in. Thanks for those insights.

Yeah. Yeah. Thanks, Jason.

Thank you, Jason. That covered a lot of the questions actually of just pricing and stuff. But let's call up Catherine. You had some questions around numbers. How many leads could one rep go through? Do you want to ask your question live? Sure. Yes. I was wondering, Kyle, how did the dynamic change after you mentioned you also assigned the post-sales activities to your team? So what changed then?

In terms of conversions. Yeah, the AEs don't do the post-sales work, but I, that team reports to me now. So it's still a separate group of people that are doing onboarding. I would very rarely advocate for sales reps to do onboarding. Those are very different skills. They tend to be mutually exclusive in a lot of ways. And reps don't want to do it. So they're not going to do a very good job at it. But by combining the teams, it made the managers care way more about it because they had to get in front of me every, every week, every month and like have those conversations. So the managers caring about it makes the reps care about it. Then we updated call scripts and handoff mechanisms every month in the MBR. We're revisiting customer quality by rep so we can see who the reps are that have quality problems and not so we can coach them. There's, yeah, there's a lot in there.

Got it. Thank you.

No problem.

Alex, your question, you have a couple questions I know, but the question around hiring, where do you recruit? Do you want to ask that? Because I think that's probably important if people want to know where you can get these boiler point hires.

Boiler room hires.

Yeah.

Yeah.

Thanks, guys. Well, first of all, thanks for putting this together. This is, this is gold for us right now. We're looking to hire these candidates and it feels like every candidate that comes across my desk has an enterprise sales background and I'm so skeptical that they're going to be able to pivot to SMB.

No, no, they won't. Hard no.

Yeah, exactly right. They want this huge infrastructure around them that we'll never be able to provide. So how are you recruiting SMB talent that has experience that can do that work and has that commitment and passion?

So how do you screen them?

How do you—

yeah, yeah. Um, so this is different depending on who you are. Like, I have a bit of a following now, so when I post roles, I get smashed with applicants. So my approach— you want to post my role? Yeah, there you go. Um, but let's assume that you're— it's like less brand equity, you got to go outbound. So you have to figure out who are the— who are the, um, who are the other startups that are like a little bit ahead of you that have a similar audience, a similar customer. It doesn't have to be the same product. It doesn't have to be the exact same customer, but it has to feel and look similar. And you want to go maybe like a one stage ahead and find the reps that have been successful there. They know what good looks like. Um, and then they can come in and replicate some of it because you won't be able to train them a ton. Most likely if you're a founder or an early head of sales. So you want somebody to have some pedigree and some skill, but they can't be from— not can't, rarely does the big Salesforce hire work out for you because it's just such a different environment. So they need to have seen a startup. They need to come from a similar segment like our SMB reps from SMB companies. And hopefully they are familiar with your buyer. Like I would never hire an HR rep to sell to restaurant owners. They are so brutally different. You know, like our customers are smoking cigarettes on our demos and swearing and like I have a blast with it. Our reps have a blast with it. But like that's a particular type of person.

For sure.

You want to go find somebody who's like, we hired a bunch of people from Procore, like a company that Procore hired, acquired. They were a stage ahead, Series B. They sold to contractors. You can figure out how to sell to a restaurant owner. So there, there's some of those, there's that matching that's really important. And then you gotta like build your pick list and then go outbound with really targeted messaging and be really consistent about it. It's just like running a sales campaign and just pay a little bit more, honestly. Like if you want the top, top talent, I advocate for less reps, pay them a little bit more, uh, especially in the early days. That, that would be how I approached it.

Well, thanks.

And Sam Blonde has a bunch of really good stuff on his new podcast that he did with 20, uh, on the 20VC feed. Uh, he breaks down a whole like first sales rep hiring framework, which I like a lot. He had good mentorship.

Shout out to Sam, that's awesome.

Kyle, how much time would you say you spent— it's Jason M. Lemkin, and then I'll let, let save room for one last question too. How much time do you spend on in your each week on recruiting?

Depends. There's a lot of weeks where it's like 15 hours.

15 hours.

Yeah, less, less now because I just filled that VP sales role. I don't have any open managers. Um, but yeah, when I'm in the thick of it, I go hard. Like I did, I kept a really high bar for that VP sales hire and I still met 22 first round candidates, spent 45 to an hour with every single one of them, 6 case studies. That's An hour and a half is the meeting. I'm doing an hour of prep ahead of time. I go really, really deep on it.

Yeah. And I write 22 first round meetings so that you qualified or the team qualified for you.

That I got—

you call it—

I don't do pre— I rarely do HR prescreens.

Got it.

I can let them all—

all the leader candidates, you had them do the classic full case study of what they would do for their 60-day plan type thing?

No, I had them present me a strategic project that they had already done. I wanted them to present something they were familiar with. The, like, what would you do in your first 90 days, I find to be pretty abstract and, and the, it's like generic, but like, bring me the, the gnarliest strategic initiative that you ran personally and talk me through it. Cause then I can really prod at that and, and, and ask tough questions on it and they'll have the depth there. But if you don't, And so like also content for me is part of recruiting. I write multiple times a week on LinkedIn now, and that is all content that is all candidate attraction. I don't write content for my customer base because they're not on LinkedIn. It's all manager and rep oriented. So that's like, you know, 3 hours a week, but that's why I get the application volume I do. And so, so if for me, that's my strategy that takes a long time to build up. For other people, it's like 2 or 3 hours of just cold prospecting, hitting people repeatedly, finding their phone numbers through ZoomInfo and texting them, hey, I reached out on LinkedIn, I'm the CEO of whatever. You got to BDR hard if you want good talent.

You got to do it hard, right? Yeah.

Like there's nothing more important than recruiting, arguably, as a founder, as a head of sales, recruiting and then managing that talent bar.

Yeah, I think 15 hours a week is a good, a good simple way to summarize it. One, just one really, you said something I think on LinkedIn that was what I've come to the conclusion of, but if, and I might have gotten you wrong, but when I say this, a lot of revenue leaders criticize me for it, but I want to hear your thoughts, which is if someone doesn't do substantial research before that first call, there's just no chance. Like I don't even want to talk to them. Didn't you write something like if you can't watch an owner video or two or understand what we're doing.

Yeah.

And I just get so frustrated with sales. I get on a call with the sales rep or sales executive and they're like, tell me about the company.

Yeah.

I feel like that's a question of death. Tell me about owner.

This is this weird like anti-capitalism, anti-oppressor oppressed thing that we have in our society these days where it's like you can't ask a candidate to do anything. You can't ask like, I don't expect anybody to do it. It's like, yo, then you don't get the job. I don't care. Like, yeah, you don't, you don't have to do any research, but then you don't get this really good job. And so yeah, I expect people to be prepared. I film this like pre-watch video. I think that's where you saw the comment. Mm-hmm. So I film a video, a little bit about the company, a little bit about the role and my culture, cuz I'm, I'm trying to like have people opt out if they're not into the intensity that we wanna run at. So I, I'm meeting the candidate halfway. I'm giving them a bunch. But yeah, if you've done no research, then on my scorecard is preparation and conscientiousness. Those are two of the criteria. And if you don't do it, then how are you gonna— you're gonna show up on a sales meeting having done no research? That's my view.

Like, you never, you never get better at sales after you hire someone.

They get—

at best, they're the same.

Yeah.

If you can't sell yourself, you certainly can't sell restaurant marketing software.

Yeah.

Counterintuitively, yeah, there's a breakpoint to, to that. Like, I've actually had some candidates over the years, they go so crazy hardcore on preparation and they're over the top trying to win the job. And I used to love it, and now it's like a little bit of a flag. I'm like, you know, does this person need the job so badly that they've had to go this over the top for it? I, I don't, I don't have a strong opinion, but I've noticed this pattern where We've had a couple of people that have gone the most over the top in the interview process and they haven't worked out. And I don't know what's driving that, but I think they lack—

it's my experience as well. I think that's a much smaller issue than the folks that don't want to do it and do any preparation these days.

I—

yes, I think they lack the— there's a certain type of EQ you need to be successful in sales. You need to read the room, right? You need to be good at the product.

You need to get it.

If you overprepare, you're going to, you're going to waste too much time on everything in the sales process. You'll never close anything. Yeah, you'll never close it. Yeah, you got to close 20 deals this month. There's a certain amount of time you put into each deal. But yeah, that's a, that's a, that's a good insight. I like the tip. For what it's worth, I will change this myself. It's obvious now that you say it. I like the tip of not just asking people to go watch the owner video, go look at the website. Right. Which is so easy. Right. I like the tip of like making a video from the hiring leader. Here's what I want to want from the role. Just so you know all the questions. Here's how hard we work. Here's what the team does. Here's what it's like.

Yeah, we're a performance culture.

Yeah, this is exactly what it is. And so if you haven't watched that video, if you watch it and you opt out, even better, right? It saved everybody time, right?

Yeah. Radical transparency is my approach in selling, in interviewing and candidate stuff. I just want people that match what we want to do. And, and if they opt out, it's like, oh man, this was a good candidate. We lost them. It's like, no, no, you lost somebody who was going to not work out and you were going to spend a bunch of time on anyways. That's a hard lesson to learn.

All right, Caitlin, are we out of time?

We're out of time. So many great questions in the chat. So sorry if we didn't get to them, but head over to Kyle's LinkedIn page because he does post a lot of content. A lot of people were already recommending that and he will post that monthly business review template hopefully for us.

I will. And I'll do a—

we'll put it on the Saastr post that comes out of this too. So it'll be on Saastr soon.

Cool. I'll do a post, uh, like a Saastr workshop follow-up. You can drop your questions in that thread and I'll answer every one of them if you want.

Awesome. Yeah, I can share the questions with you as well, Kyle. So that makes it easy. Um, thank you so much. Great. Um, great week this week. Great content, great interaction. So thanks everyone for joining. And of course a big thank you to Kyle for sharing all these insights and tips.

Thanks for having me.