How Cledara Scaled from Founder-Led Sales to a Highly Repeatable Sales Org | Brad van Leeuwen

Welcome back to From Start to Scale with Alex Newman, where founders, CEOs, sales leaders, investors, and the best of the best share their strategies and tactics, how they scaled their business and broke through the next level. Hear what worked and what didn't so you can avoid critical mistakes and scale your business. Now let's get into it. Welcome to the show. Today's guest is Brad Van Leeuwen, co-founder and COO at Kladara. Kladara's mission is to make SaaS scalable for the companies and people that use it. It's one place to manage all your software subscriptions and save a ton of money. They've raised over $24 million in funding. They have thousands of customers all around the globe. Brad's been on both sides of the table as both an operator and an investor. We have so much to get into. This is going to be a lot of fun. Excited to have you on the show. Welcome. Thank you very much for having me. I'm excited. So this is a really, really cool story. I'm excited to dig into it. And you have a really interesting background. You have a lot of experience. And so I think a lot of these learnings are going to be pretty powerful. Where I'd like to begin is when you guys first started and found Product Market Fit, what does the team look like? How did you actually figure it out? Provide a little bit of context for us, and then we can kind of hit the ground running and go from there. Yeah, for sure. So in a lot of ways, we had product market fit right from the start. So, you know, the reason we'd started Clodara, both Christina and myself had experienced the problem that we solved at different companies kind of at the same time. And so we knew we had at least two customers that wanted to use us. We knew exactly how to solve their problems because they were our problems before we were there. But that was really just like the start of a long journey. So, you know, we raised a very small amount of money, you know. less than 50 000 built an mvp got those first two customers and then we started going into listening mode so for us it wasn't so much around the question like what problem were we solving and how should we solve it but understanding more deeply about the whole problem space from those first two customers and the first 10 customers the first 20 customers because though we understood it from first principles you know we didn't know all the parts that happen in the water under the water line so sas touches a lot of people in the organization it's not just you know how do we buy it which was the perspective that we were looking at from how do we buy it how do we manage it but it was really like as a finance leader how does SaaS across the business affect me? As an IT leader, how does it affect me? As a people leader, how does it affect me? And so from there, we spent more than a year just having a lot of conversations with the market, but also with existing customers to say, what problems are you facing and where we spotted patterns? We went out and built those new features. That's kind of interesting because I mean, an easy way to say what you guys do is you can look at all the different types of SaaS. like packages or subscriptions that a company has and put them all in one place and actually able to see everything that's going on. And then you can obviously do a bunch of things with it. But what I'm hearing right from the get go is right out of the gates. You knew obviously from from both you and Christina's backgrounds is you knew that this was not a one touch department type of thing. People make decisions as a group, especially when it comes to money. And so. inherently what you're doing is, is you're actually figuring out this approach to say, well, what does the finance department think? And what does the IT department think? And what does the sales department, like you're, you're ultimately thinking all those things through at the earliest, earliest stage possible. Yeah, for sure. Like if we were just building a spend management platform, like brecks or ramp or something it's very simple right person goes out they buy desk chairs or donuts they pay for it they take a picture of the receipt finance is happy someone's got a donut to eat in a chair to sit on job done the fundamental difference with software is that you know they're big commitments they're ongoing commitments right they're subscriptions they don't just affect the buyer they affect at very least the buyer's team if not the whole business and not only that they don't just affect you they change the way you operate and they create work for others downstream right if someone buys software for sure the it team need to know but for sure the finance team are going to figure out about it one way or another and they're going to have work to do every month and so figuring out how we can bring all those jobs to be done from a single source of truth so that instead of a lot of people having to work for their software their software could go back to working for them that's really interesting I'm curious, from the very, very get-go, you guys had some hypotheses. And then you started talking to all these different people. And you were doing a lot of different outbound. You really focused on having conversations. Is there a core competency or is there a specific kind of theory or hypothesis that you had that you ultimately changed based on all these conversations? You know, I think, again, we were our first customers. a pretty strong view of what needed to be done and how the product needed needed to do it i think you know there have been a lot of things along the way particularly around the edge of our product so sas management certainly then it wasn't a defined category and it still isn't today so simple things like what is in scope what what should be a feature that goes into this category and what is out of scope is something we're testing all the all the time we had this idea quite early on europe had passed a law that said if you were a fintech you needed to do vendor risk management and you needed to answer these 80 questions about every third-party vendor you worked with including sas and we thought uh-huh there's a lot of fintech in europe if we go build a feature that made that really easy we'll get all those customers And in the end, you know, we spoke to people. They were excited about it because they were thinking about how they had to do it. In the end, nobody cared when we built it. Luckily, we built it in a really light MVP way to test the idea. But nobody cared. What we learned through that is that people have to say they care about compliance. They can't say they don't care about it. But are they actually going to spend money and do it? Now, having said that, like it wasn't. a massive failure because that feature stayed there a very small number of customers care about it deeply and now that we have slightly larger customers what we've learned is that that regulation actually maps really well to like SOC 2 or ISO 27001 and so that feature has started a lot of great conversations with newer customers more recently that are not fintech they're not in Europe they're in US and that's helped us close deals so we were kind of right after being quite wrong for yeah Well, that's a nice way to think about it. I know that you're a big outbound, go talk to customers kind of guy, go talk to people out in the market. And I know that's one of your keys is to say, hey, get out, do outbound as early as you possibly can. Can you give some light as to why are you so strongly in that direction and some of the things that it ultimately helped you do because of it? Yeah, for sure. I remember I came to this idea not so much in sales, but as a kid growing up playing basketball. It's a lesson that stuck with me for life. So I was too slow to be as short as I was. I either need to be much taller or much faster. And so whilst I was reasonably competitive at basketball, I got frustrated, right? I was not the best player on my team. And I remember growing up, at some point, my dad told me, like, stop complaining, just go get the ball yourself. Just go get the ball. And that helped me be a marginally better basketballer, but certainly in business. Rather than waiting for things to come to you, it's so easy to do a blog post. It's so easy to pay for a Google ad. It's really hard to pick up the phone and talk to someone that you've never spoken to before. But it's the best way to have conversations. And unless you have conversations, you're not going to learn. And like this is something that we did very, very early on in our journey. So, you know, we built our MVP. We had customer one, which was the company I used to work for, and customer two, the company that Christina used to work for. But after that, we were like, look, let's not focus even so much on sales, right? Let's not count what's coming out of the bottom of the funnel because there's so much we need to learn. We need to learn like how to message our product, how to position it, who we're selling to. how to articulate their problems in in their language what else is going on in the market how can we bring more people into our tent and so we had this metric where we just had a kpi around how many discussions we were having with people outside of the business every day and it didn't matter if they're a buyer or not they could be I don't know, an influencer or someone who could just use software. Right. But we would have more and more conversations. And eventually, you know, that led to being able to talk about things in the right way. It helped us build the muscle about going outbound. And then it certainly set the tone for our sales motion after that, which to this day is is primarily outbound. That's interesting. So when you when you think about it, I mean, this is. I don't know, I want to say pre-product or MVP type product. Like you didn't have this like full-fledged type thing going on. I mean, you had a few customers that were more friendlies than anything else. How do you really, how do you start selling via outbound without all of this? I mean, is it a confidence play to say, this is what it could be? I mean, with a KPI measured around just like the number of conversations, like, are you actually trying to sell? I feel like so many, so many founders are saying like, well, I don't have anything yet. Like, how am I supposed to sell it? Like, how am I supposed to deliver it? I don't have any of these things. Like, how do I even do outbound? And then it's this catch 22 constantly. Yeah. So our MVP basically then was like a list of all the software that you had in the business. And the way it worked was you could click a button, get a new virtual credit card and pay for something new. And once you paid for that thing, it added it to the list. Right. That was the thing. And the real value prop, the cool hook was click a button, instantly get a new virtual credit card. Click it 100 times, get 100 of them, right? It had value and it did solve a problem for a lot of teams that were putting things on personal cards or not really having a process around it. So we knew it added that minimum expression of the value that we wanted to create. But we didn't really focus on selling, right? Like we just focused on learning because we knew. that that minimum expression of the value we had wasn't the product we were going to end up with but it's how we could start the conversation and look there were customers that got value from that very basic feature set very early on and but most importantly it meant that we had the phone number of a finance leader that we could talk to that cared about our product and would tell us what what else they wished it would do that's interesting it's it's great advice i mean if you focus on trying to sell They're going to give you advice. And if you just focus on trying to learn and ask questions, you might actually figure out where your business actually has an opportunity to go. And oftentimes they're not, they're going to go, well, so can I buy this? You know, it's really fun. I remember that we'd sort of gone through this mode where we would talk to anybody that would talk to us, buyer or not, and that we learned a lot. And then we're like, okay, now we need to, now we need to start doing some proper outbound, right? Like sending emails. giving a message, trying to get a, get a meeting. And this was, this was fun because obviously we didn't know how to talk about our product yet. And everyone that's done outbound knows that they're going to get a lot of four letter words back from time to time from people that think they're responding to a machine or someone using sales loft or something. And at the time we were not, we were just like typing them out. And I remember like we probably got. half our first 30 customers that we'd got through Outbound, where someone had sent me one of these really rude messages back. And I would go back to them and say, hey, it sounds like, you know, you think really passionately about this. As a founder, that sounds like a great learning opportunity. Could we have a chat? I'd love to learn more. And they were like, you know. shit, this is actually a human being. I would never talk to a person like that in a bar. I'm kind of morally compelled to take a call here and help this guy out who's trying to build a business. And then we'd learn more about the problem and occasionally we'd get a deal from it. It worked really well. It's a lot of learning. I mean, everything you're saying right now is just learning, learning, learning. I mean, it kind of changes your perspective. So let's fast forward here. So you start to have all these outbound conversations. You learn a bunch of things. How did you know that you truly had product market fit? Obviously, you're solving a problem that you both have had in your own businesses. You're getting some customers, so it's not that you have traction that way. But how did you know you truly actually had something? I think the key thing with product market fit is with all products, as long as the onboarding is not too hard, as long as the cost is not too high, you're going to get customers come in the front door. The way you know you've got product market fit is if they keep using you and they don't churn. And of those first customers that we had, you know, certainly the first two are still customers today. One of them is quite a large customer and many of the other 30 are as well, right? So we knew that we had a product that delivered value. Our challenge then became a little bit different. It's like, how do we help more people find out about this thing that we know can help them? that then raised the question like what is our go-to-market motion do we want to focus on outbound and if so what's our next step here because at the time christina and i were doing sales doing support doing product doing everything because it was there were four or seven of us four engineers christina and myself and a graduate that we hired in the pandemic in the local like the village pub and you know he said he had our social media account and so to scale it up we had to take some sort of different approach than what we were doing and figuring out what to focus on well no better time like the present let's dive into that like how do you actually figure that out i mean so much of you know so so much of dice could be saying hey how do you how do you look at your customers right it could be small medium large and you can define that a number of ways you could say pick up by industry or pick up by department like how did you actually figure out like what was your initial go-to-market and then we can obviously dive into some of the other pieces so we when we started out obviously we solved the problem that we solved for us and so where we started selling was other companies like us we were confident that we could speak their language we were confident that We would get speaking slots at trade shows to help build that trust from calling in favors from events we'd sponsored in previous companies in the past. So we started selling to companies like our small tech companies because we knew that if you use software, we were valuable. And the easiest way to know if you use software is if you're a software company. So that's where we started. The big decision, it was a really important decision for us at the time, was we needed to make a first sales hire. We knew more or less what language worked. Outbound was a hobby. We hadn't done it in a scalable way, but we knew we could get demos. Once they were on a demo, we knew how to demo the product. We weren't very good at discovery, but hey, we could give a killer seven-minute demo of our product that would close. We were too busy to follow up real well, so we knew there was a good opportunity to close more deals just by having more capacity and following up better. So what we did was we decided to hire... our first salesperson and our approach there was we wanted someone that could be full stack so they're like a head of sales of a team of one and the person that we hired oscar we'd bought from before rather christina had bought from before and this was two years previously the experience of buying from him was so good that two years earlier christina had said to him oscar i'm going to hire you one day And so, you know, we'd like got to a point and we're ready to hire and we, we reached out to Oscar and said, Hey, Oscar, do you want to come work for us to be head of sales of a team of one? And if it works, we're going to scale it up. And fortunately he said yes. And, and it was a really great decision for us. Yeah. How that's interesting as a, I haven't heard that one from a hiring tactic to say, Hey, hire someone that you've bought from. Cause that was probably a good experience. Granted they, you know, not, not a luck thing. What was it that you were looking for that embodied this person outside of the experience that you had? But it was like, how did you know that this person could be the full stack rep? How did you know that they could thrive in such a young company where there's not a lot of structure? How did you know all the different things? Because a sales rep at that stage and a sales rep at Salesforce today and a sales rep at where you are currently, those are three different types of reps right there. Yeah, it's a really great point. And look, frankly, I'd like to say it was great strategy, but we got lucky. The one thing that was important for us and the reason why two years before that, Christina said, I'm going to hire you one day, Oscar, was that we really felt that he shared our values. And I believe this to today that the majority of interactions that the the market, the world at large has with your company is through sales, right? They're having conversations with people. And so as a founder, like to hand over the reins of that is, it's a hard thing to do. And so having bought from him and knew that he was going to be such a good steward of our values, our focus on quality, our attention to detail. And we knew that, you know, succeed or fail, he would try really hard and really care and do it in service to the greater mission that we're on meant that we just kind of guessed he would be the right person to figure it out. And he was. That's awesome. So what did that look like? So you make this hire, Oscar starts, you and Christina are running sales, obviously. Like, is it like, I'm out, you're in, go get them, Tiger. Like, what did that actual transition really look like? And how long did it take? Yeah, so he was young. So Oscar was, I don't know his age, early, maybe not early 20s, maybe just mid 20s. He'll tell me, he'll text me after he listens to this, tell me if I was right or wrong. But he hadn't been ahead of sales before. We knew he was like a good seller. We knew that he represented our values and he'd done the AE job, he'd done the SDR job. And so what I told him was that Oscar, you're our SDR. number one, and you're our AE number one. So the SDR one, like there's an approach to that. These are the type of customers we go after. See if you can book meetings, right? And if you can book meetings, we're going to go hire two SDRs and see if you can teach someone else to do that thing. When the meetings come for the first X number of meetings, I'm going to be the one taking the demo. Your job is to learn how we do the demo and then do all the follow-up that I wish I had the time to do really diligently. And you're going to bring those deals to close. And then at some point, once we know that you're in a place to take a demo, you're going to take a demo, you're going to do all of that, and you're going to improve upon the playbook. that we've iterated towards as founders. And then once there are enough deals for one AE to take in order to close, you're going to go hire your first AE. And what we're going to do is then keep scaling those SDRs and AEs as we need to. But you're going to have to prove it out. And you're going to have to be the one that can show that it can be taught to someone that's not you and not me. I love it. I mean, that makes so much sense where it's kind of like, here, let's work at the top of the funnel. Let's figure it out. Once you get it, I'll do it. You watch me, then I watch you, then you're able to do it on your own and kind of repeat, repeat, make it better, make it better, and then off and running. How long would you say that it took for him to figure out top of funnel and how to figure out the AE side? Because you don't have a lot there, right? There's no like, hey, this is how Brad and Christina did it for so many years and just follow this and you'll be successful, obviously. Yeah, I think so. The SDR one was quite quick. so it turned out that so because we're in a new category nobody was looking for a solution to their problem because it had never been solved before but we knew very well the pain that they experienced and we could articulate that to them quite well and so we figured that out within i want to say one to two months and then you start a hiring process or bring in an sdr right or two sdrs the ae one a little longer because you know there's just fewer deals coming down the bottom of the funnel there are fewer repetitions there's a sales cycle to to think about but even that might have been maybe a month or two more i think in hindsight as we were in these very early days of building out the sales machine the one mistake we made was we were too conservative on hiring it slowed us down early on because Like once you've got two SDRs that are, you know, hitting quota and booking meetings, you should already have the third and fourth in the pipe, getting trained, ready to ramp up. Because if you wait too late, then you've got, I don't know, a two or three month ramp. Yeah. And same with AEs. Interesting. How much of it, I mean, one to two months for him to come in and kind of hit the ground running, obviously you're a great seller to begin with, but to come in and hit the ground running and kind of figure this all out in a handful of months, what do you tie that to? Is it him and just overall skill? Is it a lot of the work that you and Christina did? ahead of time as far as for a year talking to all these potential prospects customers that type of thing i mean for him to hit the ground running like that and from an sdr point of view makes him pretty pretty good impact and traction to be able to turn around and say hey let's go hire more people within a handful of months it's pretty impressive yeah look also i think it was was all those things like oscar was certainly great we'd certainly done the work i think also the other thing that you can do early on that you can't do later is you can be less efficient Right. So if you say that, I don't know, at the time our targets were really high, the deal sizes were smaller, but let's say we wanted an SDR to book 25 meetings in a month. Well, your conversion rate from account touch to meeting doesn't matter so much because the TAM relative to one SDR is infinite. but as you have more strs that efficiency rate starts to really matter and so you don't have to solve the efficiency early on that certainly helped us but what what it did do was by being perhaps a little less efficient we could get deals down the funnel learn that demo learn that close and then learn that method of teaching a second ae before worrying about having to solve something like efficiency which only becomes important later That makes sense. So right out the gate, when you hired him, you put goals and KPI numbers in place to say, hey, I want you to set X number of meetings on a weekly or monthly basis right out the gate? Not right away. So we had an idea about what might be possible. What we said is one of the things that, you know, congratulations as head of sales of team of one, one of the things that you'll need to figure out by the time it's a team of two or three is where do we set targets? right so start to work through this and tell us what you think is a reasonable target and then we can start to do the maths like does this motion work from a from a unit economic standpoint yeah no that that makes sense kind of build it as you come so then then that results back into so you're not in day-to-day selling or at least nearly as much as you used to right you now you have oscar and he's doing his thing you are you have your sales higher Growing, things are starting to go well. What did the actual sales manager, sales coach, founder, whatever you want to call it, what did that look like from that perspective now that you had all the million other things to do as a founder, but you also needed to manage a salesperson? And there was a lot of challenges there, both for that. our head of sales the team and and also me right we're all figuring out what's what was important whilst it was happening and and generally what we found was we only knew what was important when it was already in the rear vision mirror and we realized we did something well or poorly i think the oscar like our we we had a lot of free reign because we needed we were running very fast in a lot of directions at the same time so it was about like For me, there were two really important things. So number one, having that cadence of conversations. It was daily, right? Until people begged us to stop, our entire go-to-market team, that was sales and marketing, were on a call every single day. Every single day, all together, trading highs, lows, and asks, learning, making sure information was flowing really, really fast. So that was number one. Number two, and this still exists to this day, is that we had to set up the infrastructure to be really transparent on data. So my big thing is you should be able to ask anyone at Kladara, you know, was last month a good month or not? And everyone should give the same answer because everyone should know how to measure that thing and everyone should know how to interpret it. And so having a lot of data, you know. for from the perspective of sales like how many demos are booked how many have taken how are they converting how does that how are the different performances of the different reps how is that mapping down to our performance versus targets at a company level our revenue what's our revenue today right and and how is the work we've done influenced that and so that way there actually didn't really need to be a lot of management because everyone knew if what we were doing was working or not and if it didn't work that was okay we should just go try something else now that so at what point in time that you moved from daily to another cadence is it oscar started to build out the team a little bit more and you took on different responsibilities or like what did that look like because i would imagine meeting daily sharing all those learnings data transparency like that's That's a lot. I mean, it's obviously extremely important and right so a top priority, but it evolved over time. Yeah, for sure. So the data piece, we found ways to do asynchronously. So in our office, we would have big 50-inch televisions with real-time data on it. Some data that was designed to help us measure our performance. Other data, which just made sure you look at the screen, here all the sas products that our customers have bought in the last 30 seconds oh look it's changed again 30 seconds later isn't that cool right so to draw attention to it pouring daily data at this like the top three kpis of the company to the company to the general channel in slack at the same time automatically every single day seven days a week these pieces helped a lot in terms of the stand-ups the first thing that broke was they just got too big so we had to make them smaller so instead of having a sales and marketing one every day we had a sales one and a marketing one separately and then they got together as a go-to-market function maybe twice a week right so we we changed that and then as we you know now the team is quite a bit bigger we're 25 i think in in sales they they now have you know pods, they have pods and teams is how we call it. So small pods, SDRs and AEs together. Teams will be, for example, a group of SDRs that work together on enablement and things. You know, they have their own cadence, but constantly as things get too big, thinking about how we break them down, but always with the idea of how do we bring people together to share learnings as frequently as possible? Like a learning that's three days old is just old. right it should be it should happen every single day if possible ideally and then second of all like some obviously accountability right sales is hard but you know celebrating people that do the dials and send the emails and get that great chase is super important yeah in the in the earlier days when it got beyond oscar and you had a smaller team how much were you still involved in leading sales Like, I mean, are you reading emails? Are you digging into like call recordings and that type of thing? I still watch demo recordings every single day and also success onboarding calls every single day. Not as many as I would like, right? But I think, you know, we have to know our customer and our market and that's a great one of the ways to do it. I think, so what happened over time, so this was Oscar's first management position, right? all of a sudden managing a team that's bigger than any team that probably he'd ever worked for. Right. So I spent I increasingly spent more and more time with him and helping him on that journey as the team grew, as opposed to like. joining every sales stand up right that that became harder and i had to choose how i i spent my time especially as we were growing other teams in the business like marketing like success which also needed you know we're perhaps in a more nascent stage because they were smaller but needed different kinds of attention sure That's interesting. Tell me more what that means because it's one thing to just get in and start running a pipeline meeting or running a one-on-one, which you have your scorecards or you have your frameworks and that type of thing. But right now, you're essentially coaching a player, a coach who's figuring out both things on the fly. One is how to sell this product from them. that doesn't know anything about right two is building a team both an sdr team and an a team like there's a lot going on there's a pandemic that's happening so you're obviously not able to like see everybody face to face every single minute of the day when you say hey we're i'm really working with him one-on-one what does that exactly mean it just means spending the time right like i i would like to say there was some overall story arc or some structure some days it was super tactical other days it was you know helping him think through that what if we wanted to change comp for example how that would flow through to cac and margin and the performance of the business right so helping him understand some of the wider context that maybe he hadn't come across before he knew all the theories but just hadn't had the opportunity to have to think through it so trying to always give him more context for the decision so instead of taking a decision like a great decision as an individual contributor but a great decision as someone that's got that peripheral vision about how it affects things in the second and third order That's interesting. How much were you involved with just kind of helping build out the team versus were you trying to kind of release it and let him kind of do his thing? Or, I mean, you come up with this SDR AE model with one manager and then it obviously has grown and we can get into that. But how much was it Brad's influence versus, hey, you go figure it out and you tell me? Yeah, I much prefer the second model. Now, we're going to have a discussion once you figure it out. i don't want i'd never in anything i don't want to like spoon feed it because having been involved with a few companies now what i know what i've come to believe to be true is the problems are always the same the solutions are usually different and so i don't think there's like if there was just one way to solve every problem every tech company in the world would be a unicorn already and that's just not the not the case and so you know taking the inputs we have, really trusting his judgment. And then, you know, sometimes often we agreed, sometimes we didn't and just like talking it out and talking about why. Yeah. You said something, you slipped it in there. Trust. I don't think that trust that I see in some of the most successful companies, the ones that scale the fastest. There's a lot of trust between founders and kind of leadership team to next level leadership team all the way down. Trust is so key. Otherwise, it's going to take forever and good people are going to leave. Yeah, I think you have to trust by default. You have to start from trust and then, you know, you of course calibrate, right? It doesn't mean that someone has to take all the same decisions as you. They just have to know like the types of things where the materiality or the novelty. of it or the risk of it means that you need to kind of discuss it before running ahead or whether it's a situation where you can can run ahead and i think the most important thing is that if you know if uh if trust was a deposit account it starts at 100 it can go up but it also can go down and i think making sure that it always goes up is really important because once it starts coming down it's really hard to reverse that there's hard to reverse gravity You figure that out and you're a rich person. So this is all happening and you're starting to make some pretty good progress here. Team's starting to grow. What does the actual kind of go-to-market team look like? So you have your SDRs, you have your AEs, Oster's kind of leading the team. I mean, what does marketing look like? What does CS look like? Do you have RevOps, SalesOps, something like that? Like how is everybody actually org together? Yeah. So by the time we'd raised our Series A, we, you know, we had a marketing function, right? So the way I would, where our marketing function was strong at this point was, you know, really around, really around brand. It was strong around, you know, collecting testimonials. It was strong around providing collateral to salespeople. It wasn't. It wasn't yet like bringing in opportunities for AEs to close, right? That we were not there yet on. We also had a really nascent success team. So we, our CMO at the time, he'd been at a bunch of tech companies. We didn't know what CS needed to be at Clodara. So, but we knew we needed something. So we said, hey, Rob, go out and hire, go out and hire. our first two cs people see what that looks like so we had something but we didn't have very much structure yet and that was that was really it we i don't remember if we had sales ops yet we had it like right around that time but effectively within sales it was our head of sales and a bunch of aes and a bunch of sdrs and that was it and you know we learned a ton of lessons about why that probably shouldn't be it I'm curious, what's one or two that pops off the top of your head just because we're on the subject? Yeah, I think sales ops or revenue ops is important. So how you can automate as much as possible within the business. So identify in the go-to-market motion where there are opportunities to optimize either in terms of automating processes or automating the way we figure out like which of these accounts in Outbound we're going to prioritize and put extra effort into. that's a really high leverage point around integrating all the tooling the other thing i think that we did not well another two things we didn't get right so we the way i saw i sell and the way oscar sold was hey we're smart people we love figuring it out we think everyone the whole world should operate that way too and obviously that's not the case and so we didn't have anything around enablement we didn't really have a structured onboarding program we didn't do enough to set new hires up for success particularly sdrs that were often in their first job when they when they join us and then the other pieces that we didn't get right and we're still iterating on but i think we're doing a lot better is that we had you know by the time the team was this big bunch of sdrs a bunch of aes all rolling up into a single person we needed more structure and we you know we needed more experienced kind of people in the middle so that one person didn't technically have to do i don't know 25 one-on-ones every month so when you look back on it is there a signal that you could point to to say you know hey this is when i would have hired you know sales enablement or hired sales ops or you know here's where i would have hired you know a more quote-unquote experienced sales leader like you how do you think about the woulda shoulda couldas or if i had to do it again type of things You know, it's interesting because in a perfect world with infinite capital, you do all these things really early. The challenge you have is you need to decide how you allocate capital within a team and across teams. And so, you know, would it be great if we had, you know, more managers, more experienced managers? Would it have been great if we had a sales trainer early on? Would it have been great if we had sales? Yeah, it would have been really awesome. And probably we should have done things a little bit earlier than we did. But that's only because we know how it worked out. I think in the time, you kind of have to wait for things to break because in a startup, right, if you build everything as if you're, I don't know, Salesforce, when you've got a million dollars in the bank, you're just not going to get there, right? You're building like a school project or something, not a business. Yep, that makes a lot of sense. So when you think about it, is there anything that you would say, hey, if I had a chance, I'd do it differently? Or is it like what I'm hearing a little bit from you is to say, hey, if I had infinite money, I would have done it a little bit differently. But I probably would do it kind of the same way because we had to, to your point, you had to do it, let things break a little bit. We were a month or two or three or four behind, but we weren't like six years behind. Yeah, I think there were maybe some things we could have done earlier on around creating more structure within the team without adding. more people in sales that weren't carrying quota right but how could we use the resources we had within the team to provide new support so things like right now one of the things we've done that's helped a lot is group SDRs and AEs into pods so that an SDR is going to be booking for the same AE so they can they can see their deals from the cradle to the grave that it speeds up their learning and and just by the way things work, AEs are going to be more experienced and further along in their career. So they've got someone with them that is aligned and interested in their success and will help them out, even if their job is not managing that person, but just closing deals, right? Their interests are aligned that way. Now, that's interesting. How do you think of kind of the SDR to AE relationship? Do you have it so that they're segmented by deal sizes, industries? customer profiles? I mean, with 25 salespeople on the team, like how have you segmented it out over the course of growing it? So we've experimented a little bit segmenting it by geography. So effectively US and not US, right? So we've learned that people in the US like to buy from people sitting somewhere in the US. That works well. People in Europe don't care. right they're used to buying software from people in other places we starting to think about how we can build expertise around narrower verticals than we currently define them but we're we're still early on in that process i think when it comes to particularly strs the biggest lever that you have is around helping helping them build their knowledge in the persona that you sell to and the product i think the industry and geography are dimensions which at some level of scale are valuable but less valuable because you know in our case all things being equal a finance person that is sitting in san francisco is generally doing the same types of jobs to be done as a you know the same person doing the same role in book arrest you can see that that's interesting so I mean, one of the things that you hear a lot about from SDRs, or maybe it's a complaint, is to say, I am, you know, to your point, this is my first job ever. I don't, and I'm selling to the head of finance. What can I possibly say that this guy or this gal is going to be able to go, I want to take this conversation. To your point, like having them feel it is a huge, huge thing. obviously there's all the training and, you know, you write it in this way and that type of thing. But like, how did you get, how did you help SDRs learn it so much faster to be able to make that impact? You know, I think that the training and the onboarding is, well, the ongoing training, but the initial onboarding is really, really important. But the thing is, even what I've come to learn is that The best SDRs, even in the absence of any training, in the absence of any onboarding, they always get there, right? So it's the cherry on top of the cake if you can train them a bit. But the smartest, most driven people just figure it out. It doesn't scale real well, though. Sure. So with that, tell me a little bit about how you guys hire. because you that must mean you're looking for a specific type of profile or specific types of attributes that you just don't compromise them yeah so there's part of it about what type of people we hire particularly as sdrs and the second of it is about our process so In terms of the process, maybe that's the easiest place to start. We do some things that are not earth-shattering, which is we do a screening call to check that we can have a decent conversation on a telephone. We give them a take-home. The important thing is we always give feedback during the take-home. Some are excellent, some are average, but we always give feedback to see how coachable they are. We always have them meet a peer as well. The best SDRs are the best screen of. future great sdrs and then we all either christina or myself will interview everyone that joins the company and that's not so much can you do the job we trust that by the time a candidate comes to us they can do the job we believe they can we've interviewed them for values because we think that the values help you in two ways so as a team we can be super diverse but if we operate from the same sense of values we're going to function really well as a team where they you know no matter what religion gender sexual preference whatever those things are same values we can we can work together and the the other piece is that we believe that people that exhibit our values are the types of people that express things like curiosity right which is actually one of our values and if you're curious that's a necessary but not sufficient condition to go figure it out for yourself so that's the interview process and then in terms of the candidate look i i'm a big believer in hiring people for their strengths not an absence of of weaknesses we look for competitive people you need to be competitive in sales we have a lot of former professional sales sports people on the team that you know maybe they've retired maybe they reached a really high level but not a not the place um where they're going to go on and earn a great living doing it they're looking to take their first professional job and look they're just used to doing the repetitions and they're certainly used to failing because it's It's really hard to hit a golf ball perfectly on every swing, right? They're used to practicing. And, you know, they're great fits for the team because they're used to doing the work, learning, and figuring it out. No, that makes a lot of sense. I think there's a lot of good attributes in there. Coachability, curiosity, competitiveness, those are all... those are all big ones that i also look for i mean curiosity is just such a such a gold mine right there i mean if they're if you're truly curious and you can look at it obviously in a bunch of different ways about the company about the problem about so on and so forth that person's just naturally going to go over the top and they're going to do the work that somebody who's not that curious isn't going to do so that makes a lot of sense so let's talk a little bit about kind of where you guys are at today because with 25 people you're right You mentioned that the 25 one-on-ones that obviously only can happen for so many days before you crack. But what does the team look like today and kind of how is it structured? Yeah, and this is a thing that we're still iterating on. So now Chris has joined us. He's our current head of sales. He used to lead sales for Northern Europe for Box, right? So he used to running big teams, used to operating at a high level, knew what, great look like actually had done that stuff before and so that's that's been the first change we've we've reorganized a lot the sdr team so as i've talked about pods i've talked about organizing them into sdr teams that work on enablement together we've added a person to focus on onboarding and enablement for particularly for sdrs who actually side she was our third sdr hire she's awesome really lucky to have her and and she's just been so great in thinking from first principles what does onboarding look like for a newly hired sdr the we've added two sales ops people so we added a sales ops person that turns out that once you had a sales ops person that can do fun stuff with salesforce Success and marketing really want a lot of their time as well. So we've hired someone with an engineering background to be a second sales ops person to scale that. And now we're thinking about how we add extra structure within those SDR teams. So who's looking at currently hiring and interviewing for a head of sales development. And the other big piece where we're in the process of doing is actually on product marketing. We haven't had a product marketing function before, but how can we embed a sales centric product marketer within sales to join those conversations, to ask those questions and really distill that optimal messaging positioning and everything else that's driven from that so that sales people can be the most effective they possibly can be, but so can everyone else in the business so we can understand really how to speak the language of our customers. That's really interesting in just how the team has ultimately evolved from, you know, SDRs, AEs, and then obviously to what you have today with marketing support, you have sales ops support, you have kind of the go-to person who's done something like this before. When you think about where you were to where you are today, like what do you point to as these, like, hey, I made this bet and it absolutely worked, or I made this bet and maybe should not have made that bet before. or wouldn't make that bet again i think in terms of bets i think they've been too big from a business go-to-market standpoint there have been two big bets that really have paid off so the first one is around pricing and packaging we're in our fifth generation of pricing we increased our pricing most recently eight days ago i think to be substantially higher than than what it was before and i think the reason why this is a bet is obviously you don't know if you can sell it especially in a new category you don't know if you can sell it until you try it's high risk because aes want products that sell but also it's high reward because you can grow faster and what ae doesn't like a higher acv product they can sell to the same customer with the same sales cycle and so that's worked really well every time so far and i'm touching wood here you can't see me off camera but i'm touching wood Saying that every time we've done it, it hasn't had a material impact on sales cycle. It has not had a material impact on win rates. And we've not had to go to a different market segment or move up market or anything. And that just means, you know, more growth, which everyone's happy with. And then the second piece that we've done is around the second bet was around investing much more heavily in customer success since the turn of this year. So we hired a really great VP of customer success. So Amy. joined us here in denver actually she was the 21st employee at sengrid she was running sale support services and success for them almost all the way to ipo and so bringing her in focused entirely on success it's been a game changer for us in terms of revenue right because we get we make more revenue when our customers use our product We get less churn when our customers use our product. Not that churn was ever a big problem for us, but it just made a good thing much better. And also, for the first time, we were doing upsells. And so that has given us another lever to grow revenue, to complement all the good work sales was doing. And it was substantial for us because with more than 1,000 companies using us, you can have a very big impact on revenue today just by working more closely with 1,000 customers that already like you. Interesting. Yeah. I mean, and you can learn so much. I mean, you take all that and you funnel it back into sales, marketing, plus customer success can use it to better customer success. When you think about this, I mean, you're in scale mode. I mean, you're in growth mode. You're investing in all these different areas of the business. How do you do it in any kind of efficient way without just burning the bank down? So one of the virtues of starting a company in Europe is that you just don't have people throwing money at you at 200 times ARR, right? And yet the metrics you need to hit are the same or higher, right? So in terms of you want to go raise a round, it doesn't matter that you had a third of the money, you've got to have double the revenue of what it would be for a similar American company. And so we've never had any choice but to be efficient, I think. What's helped us? are a few different things so we that focus on that shared understanding of data and the transparent data that enables that is really really important because then everyone can see how you're allocating capital and everyone can see the result either it worked or it failed if it failed that's okay just don't fail the same way four times right go do go do something different the so that that's been really really helpful and i think the other thing is like a hiring choice i think in your leaders you need to know if you're hiring a spreadsheet or a novel now novels and spreadsheets don't talk real well together sometimes you need a little bit of the novel especially in in marketing but you need to make sure that if it comes down to how do i allocate capital you have leaders that understand the impact of how that capital is allocated both with them immediately and through downstream decisions right so Coming back to it, it's really easy to lower targets and increase OTE for AEs. They're going to be happy, right? But what does that mean for your CAC? And what does that mean for your LTV to CAC? And what does that mean for how you're viewed in the market? And you can have that same discussion with different metrics about lots and lots of decisions. But understanding the metrics is really, really key for efficiency. One of the things that you hear a lot around scale is process, systems, metrics. One of the things that I do with my own little company is we build up metrics-driven approaches and systems in order to be able to show the measurable growth. I think there's also a balance between becoming too focused on the metrics and too focused on what do the numbers say. A lot of times salespeople are like, you don't, you guys don't get it over there in the numbers space and on the numbers department, like sales is an art sales, you know, sales is me talking to people. How do you like, what, what did the numbers look like? Not the actual numbers themselves, but like, what is it that you're looking at each and every single day or week or month from a sales KPI metrics? And then including balance. So it's not just here's 100 metrics that we're looking at, and that's obviously challenging to make decisions of. Yeah, I think, you know, you can definitely have analysis paralysis with too many metrics. And I think it's not so much, oftentimes the decisions that you make and the changes you make, it's not so much like, oh, what's that going to do to our CAC, for example. It's more about what's happening to the first derivative. So how is that? changing it did we expect that to drive cac down and did it go up and if so should we understand that or should we run the run the experiment a little bit longer you know it's also the case that it's totally fine to have hypotheses that are not supported by data right that's that's awesome we wouldn't have a product if we waited to have data if people wanted a product right we had to go build an mvp first but you need to understand like how do you run those experiments what do you expect to happen going into it did that thing happen that you thought would happen and if not what happened and does that mean that that thing was proven or maybe it's just not proven yet or not at all and so just having some intellectual honesty around that i think you need to run experiments you need to try new things you need to be aware that that they can't all be supported with data certainly as a founder you place bets all the time largely on you know instinct sometimes oftentimes with data but your biggest bets are always on instinct and that's okay i think it's just being comfortable with that and making sure that the culture of the organization understands that but you know the truth is like when you start out everything's gut driven and by the time you're you know doing your earnings call once you're ipo'd and people are you know analysts are debating over whether you miss something by 100 basis points or not then you have to be really numbers oriented and if if you're in the middle or somewhere along that journey then you just have to know that you're somewhere between those two extremes and manage accordingly When I think about some of the tests, I'm a big hypothesis testing kind of guy as well. And so I think about it and saying, okay, well, I increased my, you know, I doubled my pricing. And that's an easy test to make, right? Did it work or not? Do people still buy or is all of a sudden the ones that we think are going to buy all of a sudden delaying and that type of thing? Do you have an example of something that you have made some hypotheses around that weren't really about data and you were able to make a decision on them? the other one i think about is to make a hypothesis but you're a startup you have a finite amount of time and cash this the experiment can't last for a year to get enough data to be able to make it like do you have an example as far as like what you what you mean by that in order to kind of share with the audience yeah i think there's a lot there i completely agree that you can't wait you know any experiment that takes more than a quarter you have to really want to do and has to have potentially really big impact i think You've got to look. So a great example of this was our space isn't defined. When we came into this year, we realized, well, we'd known for a few months now that everyone wanted to cut their SaaS costs. And we knew that our customers on average reduced their software spend by 30% just by starting to manage something they never managed before. And so we had this hypothesis that we could make the like the h1 on cloudara.com basically like our customers reduce sas cost by 30 you know right that that being the h1 now we thought that would be really compelling we use google optimize i think it was at the time to a b test surely enough we got more clicks on the button next to that h1 we we probably didn't like lock in the change Soon enough, we waited for too much of a statistical certainty before locking that in. And so we'd kind of proven our hypothesis. The fun thing was we actually didn't design a good test because the purpose of a business is not to get people to click a button. The purpose of a business is to get people to be customers. And so what we realized, it took us sort of two or three months because we were not looking at this. What we realized was actually that change might have got more clicks, but it made. our SDRs job harder on on outbound because now like when when prospects checked our website it wasn't a message that really moved them to a sale to a to a purchase right we learned that actually the people booking the demo through the website like the conversion rates from that next step had dropped off and so we had a hypothesis we proved it but actually we learned that we were testing the wrong thing that's really interesting and I and I and I would bet that a lot of companies make that mistake they make the change and you say oh well this made this smoother but it actually made this other part behind it a lot clunkier so it's really to understand the full scope of that of that hypothesis and the overall process is going to be really important yeah i think that that's definitely the case and the other thing i would say is like optimizing is a really great way to find like a local maxima like the best version of that thing but actually what you don't know if you're in the foothills or at the top of Mount Everest. Right. And that's really where being bold and not being incremental, you have to be bold sometimes, even if you don't have data like we knew that that headline was some percentage better than the one that we had before. But how did we know that that was actually very good at all? We didn't or the best possible way to express ourselves. And so even once you find something that works better than what you had before, you kind of have to keep testing because otherwise maybe you've optimized towards a dead end. Yeah, it's not a set it and forget it type of thing. So I got one last thing and then we can start to wrap up because I know you got to run. So now that you've hired Chris, you've hired this sales leader who has seen what good looks like. They've done this before. They understand what to do. They're starting to make some changes. Can you point to one or two things that they've done or that you're starting to see that it's like, oh my gosh, this is what we need. We're so happy here. This is a game changer to us. So I think there have been three things. So number one, another doubling down on enablement, right? Chris being a very loud voice for the value of that. Really, really key. Number two has been around setting up kind of upstream KPIs around activities. So like it's great when everyone's hitting their number, but what are those leading indicators? that you're going to hit your number and how do we help you understand what you need to be doing you know first day of the month or first day of the quarter so you by the end of the month or quarter you're going to hit your number and so we've introduced what Chris calls the focus 250. So the activities and the process that you need to follow today to hit your, you hit your number at the end of the quarter and measuring those, communicating those, putting those on leaderboards. We never did that. I think I'm a huge, huge, huge fan of it and it's already bearing results, right? Just helping an SDR in their first job, understand how many dials do I need to do today so that I can organize my day and prioritize. And then the third thing is bringing kind of a more nuanced perspective around how comp is calculated, particularly for AEs. So making sure that we've got comp designed in a way that drives the behaviors that are aligned with the success of the business, especially as we go through these pricing changes and substantial pricing changes that change the rules of the game. No, that's huge. I mean, when prices change, comp needs to evolve with it, which I think a lot of A lot of founders fail to kind of see how everything's really, really intertwined. Not to mention what other systems, ops, other departments, that type of thing that all need to understand how this has a ripple effect. It's easy to just change a number to go up. You know, it's harder to understand what are all the ripple effects through all that. So that makes a lot of sense. Brad, this is awesome. You are a wealth of knowledge. I think we could talk for a couple more hours about how you've been able to build this. I wanted to see, is there a favorite book? I like to ask all guests if there's a favorite book or a favorite resource that you found to be very impactful that you'd recommend to anybody listening today. You know, I'm a huge, huge fan of Frank Slootman's book, Amp It Up. It's not specifically targeted at sales, but I think it's something that everyone can learn from regardless of their job. It's basically do things better. do things faster and and communicate more more candidly which is like a really simple idea but he walks through like why it's okay that you can discuss failure very candidly very directly you know you've got to hold people to a really high standard around you you've got to you've got to know things you've got to be willing to stand by the work you do and keep that quality bar real, real high, which that quality bar for me in sales is everything because they're the shop front of your business most often. They're the people, how people interact with you. And if the quality bar is not there, it's really hard to build a great business. I mean, salespeople are out there talking to your customers and your prospects every single day. So make sure you're listening to them. That makes a lot of sense. Any last remaining wisdom that you can share before we wrap this up? I think I'll share a quote, or at least the Brad synthesis of a quote from that book, Amp It Up. And that's that execution, each strategy for breakfast. I think that we can all think about what will work or whatnot. Kind of like the question you asked, like, what would you do differently? Who knows, right? Like, it's really easy to be a Monday morning quarterback. In the end, it's about executing real fast and iterating, iterating fast to keep progressing. Yeah. Well, that's great advice. How does the audience get more of you? Where can they find more about Cladara or more about you? Well, if you, for example, don't know how many SaaS products you've got, why you've got them, or even who to ask about it, you should definitely go to cladara.com, C-L-E-D-A-R-A.com. Or if you just want to chat, ask questions or follow up, you can find me on Twitter. On my personal account, it's Brad Van L. And if you really want to talk to me, my email is brad.cladara.com and I always respond to emails. That's awesome. And we'll link all that stuff in the show notes. Brad, this is awesome. I appreciate you coming on. We're going to have to, when you guys go IPO, we'll have to do this again and we'll have to hear about the rest of the story. And I can't wait to hear about that investor call. So that's going to be a lot of fun. Alex, thank you so much for having me. I appreciate it. We'll have to have you again soon. Talk to you soon. Bye-bye. That's it for this week's episode of From Start to Scale. Be sure to click that subscribe button and follow us so you don't miss our next episode. I'm Alex Newman. See you next time.

Brad van Leeuwen co-founded Cledara after living the problem firsthand - unmanaged SaaS subscriptions eating into company budgets with no good solution. He and co-founder Christina built an MVP for under $50K, spent serious time in listening mode with their first 20 customers, and grew it into a structured sales organization of 25 people.

We cover how they found early product-market fit by selling to companies just like their own, why their first sales hire was someone they'd previously bought from, and how that hire ran a full-stack solo motion before they brought on anyone else. We also get into the outbound playbook they've run from day one, including how they turned cold email rejections into real conversations.

We also dig into how they've built the org over time: the pod model that pairs SDRs with AEs so reps see deals through the full lifecycle, the radical transparency approach to KPIs across the company, and why doubling down on customer success in early 2026 became a game changer for revenue.

Good episode if you're early in your sales build, trying to figure out your first sales hire, or working through pricing and packaging as you scale.
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