How to Build Go-to-Market Efficiency in SMB Sales with Owner.com CRO Kyle Norton

In this webinar, Owner.com CRO Kyle Norton shares a data‑driven, operational playbook for building efficient go‑to‑market motions in the SMB restaurant SaaS market. He walks through the company’s growth story—from $3 M ARR at his arrival to $21 M ARR in 22 months—highlighting how early focus on deal quality, rigorous prospect data enrichment, and disciplined scaling enabled sub‑1 burn multiple growth. Norton explains three core themes: (1) saying no to poor‑fit prospects by building a machine‑learning expected GMV scoring model and tightening the ideal customer profile; (2) scaling smart by right‑sizing headcount, prioritizing pipeline health over headcount, employing a 2:1 BDR‑to‑AE model, hiring top‑performing reps, and adopting single‑threaded ownership where sales leaders own post‑sales outcomes; (3) investing early in RevOps, enablement, and operational rigor through monthly business reviews, performance stack‑ranking, and systematic documentation. He also discusses compensation adjustments, outbound mastery rooted in boiler‑room experience, and the importance of P&L fluency for revenue leaders. The session is practical, data‑rich, and aimed at founders and revenue executives post‑product‑market‑fit seeking repeatable, efficient growth.
Chapters
Really excited that this week we have Kyle Norton joining us. He is the CRO of Owner.com and his topic today is walking through how to build go-to-market efficiency, specifically in SMB sales. Kyle, welcome. Thanks for joining us.
Thank you for having me. Excited to chat with everybody today. 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, rev ops, 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. We're going to talk about building efficiency and go-to-market. Little bit about me. 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. Uh, and previous to this, I ran a quarter billion dollar go-to-market unit at Shopify. 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, um, 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 manager versus later stage when you've got support teams and other layers of leadership. But we'll talk about 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 or 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. Okay. A little bit about owner, because this is going to frame up the journey. I'm going to try to keep this as real world and as practical as possible. So we're going to 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 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've 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 dollar of revenue, you acquire, how much did that cost you? And if your burn multiple's 2, 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 1 manager, 4 reps, and early churn was a massive drag on efficiency. So it was a, 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 and we really needed to get our hands on early churn, which is going to 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 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 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 in an LTV CAC of 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 step by step how we got there. And then this year, the goal is to find the outskirts of rep capacity. I keep thinking that we've 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 the This year is all about really finding how much more efficient we can make the AE team now that we've really nailed the DemandGen 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 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 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 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. Culprit number one was deal quality. And we had a growth plan and I basically paused on it. I said, until we get, uh, churn 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 and 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 It 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, uh, 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 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 time. And he just, he basically said to me, sounds great. None of it's showing up in your revenue number. So let me know when that's, 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 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 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 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 a revenue leader partnering with your data team, RevOps, or whoever to fill their funnels with 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, 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. 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 economics. 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. 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 get a lead and it's partially filled out or If it doesn't have a mobile phone, mobile phone number, they just punt it back to the Garden of Eden and we re-send that through our enrichment flow. Because you're basically saying to your BDR team, hey, just work 2.5 days a week. That's okay. 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 in its original iteration. We figured out the data thing and now each BDR cranks out like over $60,000 in close one ARR every single month. So highly efficient. And so you just have 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 was. You like, it's, it don't bother hiring more than one or two 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. 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, 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. 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 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 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 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 is 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 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 Blond 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 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 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 get better reps, take your budget. You had 6 allocated, only hire 4, give them more pipeline and hire better reps, pay, 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, this is $30 grand more than I'm making today. And everybody's hitting quota. This sounds like a sweet deal. It's expensive in quotes, but those reps are way more productive and way more impactful for a business than hiring more Slightly less qualified reps. All right. 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 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, 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 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 single-threaded ownership. Make your post-sales problems your sales leader's problem somehow. All right. I'm going to move on from this topic. All right. 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 got to 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 like the engine of our business. Steve, who runs RevOps, has been with me for 8 years. This is our third stint together, which goes to show 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. 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 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 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. Now we're going to go into pillar number 3. We're fast forwarding to 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 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 leak and break down because it's harder to communicate. The feedback loop 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 a 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 three things, like you're really getting the Pareto principle of the high impact stuff. And then all the fancy operating rigor downstream of it is important, but if you can do these three things, you'll be in a pretty good spot. 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 RevOps team is in charge of supplementing, uh, 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 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, in, in my time. And the prep work is key here. So we're a remote company. Uh, 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, 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 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 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 two 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 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 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 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 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 send it out. I was going to say email me and I'll send it, but 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 a, an older one. It's a simple one, but it's important that you have the rhythm 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 high, especially in this market, because you're giving them valuable leads. Salespeople are very expensive. And so the— 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'd encourage people to like pretty tightly performance manage. 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. So documentation is a 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 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 faster. It's really challenging to find the time to do this, but just force yourself to do it. Put in like a, 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 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, this is the recording from a training exercise. Turn it into a how-to document, turn it into a training guide, and your, 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. 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 document. It'll, it'll give you. So 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 founders need to hire for it and coach it. And if you're 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, 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 down this path. They gotta be P&L fluent.
Okay.
That is all I had for content. We learned about how to say 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 on that growth curve. I know that was a crapload of content, but Jason, before we get to the others, hey, thanks for doing this. Yeah, no problem.
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 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 tying 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. Yeah, I don't want to overcomplicate rep comp. That's not what I'm asking.
No, maybe I think it's always a fun question everyone's fascinated with is comp, right? Maybe a different, a more strategic way to think about it is, and it goes to your earlier point about And Sam Bond'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— Owner has a decent ACV, but it's still selling to SMBs, right? So in the old days, we aimed for 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?
Yeah.
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 far can we take rep capacity this year? And so we've been pretty modest in adding AEs. 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. 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 it, that makes total sense.
Yeah, no, I want to lay out 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 skillset of the sales team. I've, 2 for 1, there was a moment, I'm dating myself. I don't know. There was a moment where outbound had its second coming. Okay. Maybe, I don't know, 2016, 2015, 2016.
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 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, but 2 to 1 may sound crazy, but I think if you're good at, if you're truly good at outbound, 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, 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.
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.
Helps to have a good product and a compelling problem to solve, for sure. Yeah.
Did you do this type of outbound at Shopify? Did you learn it on the fly at Owner? How'd you get— 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, there was a whole thread on LinkedIn this week about outbound not working from Mark from Outreach, right?
One of 10,000 threads on outbound.
Yeah, it doesn't work, but it works. 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? What's the learning? What's that process to get good? 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 soft, 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 read off a script. I'm not some like phone monkey. No, scripting is awesome. Scripting is like the most powerful thing you could do. So just thinking about it. Hey, Jeff. Yeah. Scripting is, I think, really critical. And the more tightly you can get people onto what we call golden script, the better they'll perform. Because then you can smartly A/B test what's working, what's not.
Do you think—
it's learnable.
Yeah, that's the last question I'll have. I could spend the whole time on questions on this. I think 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, the 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 grown up and you've been great at wherever, I would say primarily an inbound model, can you learn it at as your first VP of sales or CRO 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 out— 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 be— 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 go and pitch. I'm very strong agreement on that. And so they're not going to pick up the phone and make cold calls. They're not going to 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.
I like those ones.
I'm a believer. Yeah. Yeah. You'll like Brett.
All right, let's let some other questions in. Thanks for those insights.
Yeah, yeah. Thanks, Jason.
Uh, uh, thank you, Jason. That covered a lot of the questions actually.
Cool. Thank you so much.
Great, 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 those insights and tips.
Thanks for having me.
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