E7: Building a Learning and Revenue Machine with Stevie Case, CRO of Vanta

Yeah. And you have one of the best fun facts of all time as the world's first ever female professional gamer, which is super cool.

Yeah, I like the random stuff. I like— I'm very curious. And you'll— you will hear in everything that I value that I value discovery. And that is fundamentally because I love to ask questions and it gets me into all kinds of interesting things that I might not have anticipated from the beginning.

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes. But first, a word from our sponsors. This episode is brought to you by Momentum.io. Momentum is a powerful tool for turning sales and customer conversations into go-to-market data. Using GenAI, it extracts, analyzes, and automates customer intelligence across your org. The best part? It's not a new platform for your team to adopt. It integrates seamlessly with your existing stack and writes data back to Salesforce directly. Some of the most innovative companies out there, like Zscaler, Demandbase, Ramp, 1Password, and even my company, owner.com, use Momentum every single day to capture, forecast, and churn risk, autofill Salesforce fields, share product signals, and track sentiment. So check it out with a free trial at momentum.io. And so today I'm joined by Stevie Case, who is the CRO at Vanta and former VP of mid-market sales at Twilio, which was a small half a billion dollar business where she spent almost 6 years from one of their earliest reps to obviously running a massive business unit. And Stevie is somebody that came heavily recommended by a whole ton of people when I reached out for Podcast Recos. So, really excited to have you, and thanks for joining.

Thank you for having me.

So, why don't you give folks your quick 60-second background, who you are and how you got to Vanta?

Yeah, absolutely. So, I am about 2.5 years into the Vanta journey. I joined when Vanta was a Series A, kind of late Series A, although it was a large Series A at that stage and around 200 employees. So, really exciting time. We operate in the security compliance space. You may know us from the tagline, compliance that doesn't suck too much. We're all about helping unlock revenue for startups and then helping larger companies solve problems around governance, risk, and compliance. So, I do not have a background in GRC, security, compliance, or any of the things that my team now sells. So, it's been really fun to learn about that. I actually came from 6 years at Twilio prior to this, where I was in sales. And then prior to that, you know, I've really spent the last almost 20 years specializing in technical sales. So, whether that's APIs or complex platforms, typically the teams that I have sold into have been made up of developers or other technical folks with a lot of expertise. So, I get a lot of enjoyment out of that. I spent some good time in the payments and, and FinServ industry. So, did global payments platforms and ended up at a company acquired by Visa. So, had a whole adventure there. But a lot of it has centered around this idea of technical platforms for folks who create these large complex systems that have to operate globally at really high scale. So, I've built lots of revenue teams related to that. Prior to that, started my career in video games of all places, which led me into tech, but originally aspired to be a lawyer.

Yeah. And you have one of the best fun facts of all time as the world's first-ever female professional gamer, which is super cool.

Yeah. I like the random stuff.

I like—

I'm very curious. And you will hear in everything that I value, that I value discovery. And that is fundamentally because I love to ask questions and it gets me into all kinds of interesting things that I might not have anticipated from the beginning.

Awesome. And started your career as a PM, so on the product side of the house. Yeah.

Yeah. Started making games so that, that path into playing games turned into a path making games, which was not a career I anticipated, but I did 3D level design and then I was like a game producer, which is essentially the equivalent of a PM on the game team. And got involved in everything it took to make video games and make software. So that was my intro. And, you know, then moved more into mainstream tech from there. So games as an entry point was a great place because such a dynamic industry, things move very fast. You iterate on software very fast and you get very direct user feedback. So it was a great way to enter the world of mainstream tech. Although it was not something I had originally planned, it just sort of happened that way.

Yeah. What did you take, what do you take as a revenue leader from your experience as a PM?

Yeah, you know, I mean, I truly like, I will, I joke about the overlap of that like gaming experience and how you think about games and the overlap with the CRO role, but it's actually quite concrete. And you know, when you think about building games or these large worlds, these large 3D worlds, a lot of it is about asset management and optimization and the experience and how you organize multiple people through a world or experience. There's a tremendous amount of overlap with my, my current role. It's really about how do you more efficiently than the other side, get the mission accomplished, manage your assets and resources, and how do you really cohesively put together a strategy strategy that helps build a great outcome. So, I am deeply competitive. I definitely carry from that period of my life, that like competitive spirit. It's part of what I love about my current role. Like what, a lot of what motivates me to do what I do, like I love the art of it and I love the day-to-day, just like tactics of how to sell and how to build a revenue org. But at the end of it all, the thing that really excites me is the competition and winning. Like I love to win and that really motivates me. Inmates a lot of the work I do day to day.

And there's just a little bit of competition in this space.

Just a bit. Just a bit. Yeah. You know, it's, I, I joined the category leader. It's a really special company. Christina Cassiopo is our CEO founder. She created the space. You know, she came up with this idea of automating this compliance process and getting folks through an audit. And she, been, you know, a, a PM herself and really came up with this concept, created the product where none existed, had wild product market fit. And as with anything that has wild product market fit, what we saw was a whole bunch of folks create copies of that and, and try to bring their own versions of that to market. And often what happens when you've got fast follow copies is like the value prop for those things is, hey, we are quote unquote the same, we're just like cheaper or half the price or whatever. Whatever. And the products are never the same, but, you know, you put enough marketing sizzle behind stuff and it gets to be a noisy market. So I am very grateful for that. Like, it has made for a really exciting, uh, journey as a revenue leader to have dozens of competitors in the space. And, you know, we're kind of exiting the era of, of those copycat competitors now. We put a lot of focus on moving upmarket. And that has brought with it an entirely different competitive landscape of legacy players where we're now more, uh, the, the new player on the block in this like governance, risk, and compliance space. So, I've loved taking on some of these older legacy competitors as well. It's a whole different flavor of competition.

Very cool. And I'll direct people to your podcast with Mark Roberge on The Science of Scaling to talk about your ankle biter strategy, which I, I got a lot from. It was cool. One of the other things I picked up from your podcast with Scott Barker and others was this idea of you've evolved from operating with a chip on your shoulder and being a single mom in sales and all of the challenges that came with that perception to now operating from a place of abundance. And I thought this was a cool way to start the to end the conversation with this question. Can you have both? I've been reading a bunch about Buddhism and nondual thinking. Do you think you carry both of those now with you, or have you fully been able to transition into this abundance mindset?

I deeply carry both, and I always will. I believe you can change as a human. You can evolve in lots of great ways. But that underdog spirit will always live within me. You know, somebody asked me not that long ago, like, now that you've made it and you're in this role and you're doing— like, have I made it? Like, really? You know, that is just like not a— that is not a mindset I am capable of having, if that makes sense. And so, that chip on my shoulder, like, it is fundamental to who I am and how I see the world. And I think it's why I love competition so much. And, you know, when I find things are hard, what I go back to is like what I can control. I focus on execution. I focus on competition. I focus on like the control the controllables, which is something my team hears me say quite a lot these days. So you just, you know, go back to those things that you yourself can action and do. And, you know, I have added to that, that sense of a little bit more of the calm of that coming from a place of abundance. So I do feel like both of those things live in me at this point. And, you know, the first 2 and a half years of being— this is my first CRO role. I was talking about this with Christina last night, and it's like that first 2 and a half years, really hard. Like, there's no CRO playbook. There's no real, like, there's nobody to teach you how to do this job. And, you know, if you're lucky, you can witness other people doing it really well and you might get some mentorship, but there's not a book, right? There's no, there's no textbook. So the first 2 and a half years, I feel so grateful to have been in a great spot where I was truly able to have the space to learn and very grateful that things have gone well enough to like earn me the opportunity to keep going. And I do feel that something in that first 2 and a half years very much unlocked for me. And I say both jokingly and, and very truthfully, like, if I were to do it again, oh my gosh, it'd be like 10 times better next time because I've just learned so much in the first 2 and a half years. And it's unfortunate that you kind of have to learn it that way, but you know, here we are and I get to keep going. So I am trying to approach this, this next run, this next phase of my existence in this role with like more confidence. And I do feel like I put it last night as I, I feel like I've got my hands on the levers now. Like I understand how to solve core problems in a revenue organization. I understand how to move real metrics. And fundamentally, I view that as the job of the CRO. It's like, give me a North Star metric. I will figure out how to get there. And I know I know now how to pull the levers to make that happen.

And so, is that the big unlock, is feeling like you know the levers now?

Yeah, yeah. It's, you know, coming into this role, you've got like a notion of the levers and this like theoretical grasp of what that might look like. But, you know, every problem that you face in a revenue org in a company is unique. Like every company is a little bit different. Every go-to-market is a little bit different. You know, we had this discussion a couple of weeks ago with one of our investors who's phenomenal, lovely person. And, you know, one of the points he made was it's great to look at the benchmarks of other companies and, you know, try to think about like where you fit on that line. Like, do you, are you following those benchmarks? Do you look roughly like other successful companies? But his feedback was like, deeply, you also kind of can throw those out. And well, obviously you want to be a healthy company and you got like certain rules, like there's a rule of 40 and there's all these like top line rules that investors like to follow. Every business is unique and you should be comfortable straying from that benchmark line and having a point of view about why your business is unique and why it strays from the line and why that's okay. So, you know, I think you come in with this idea of a playbook that's based on benchmarks and how it's been done before. And what I feel now is I've reached that, that point of confidence and comfort and abundance where I'm like, I know what the levers are and I've got a point of view of like whether we should be on that line or not, how, where, when, why, and what we're going to do next. And, uh, that is the gift of a few more years of experience and a great network of people that I can call for advice, which is truly what has made the difference.

I think that is such a good framing because I talk about this a lot. I want people to say high probability practices instead of best practices. There is no best practice. There's a thing that's worked for many companies and it's a pattern without a doubt. And we should look at those things and evaluate them, but knowing our company stage, our market, our customer type, the reality of the macro climate means what we do today might have to be different than what was done previously. Throw in AI, throw in tooling, like you can't take this carbon copy thing and move forward. But I resonate so deeply with that feeling of you're trying to grok in that first 12 months or however long it is. Okay, like what, what does apply? What are the things? And then you, you develop that your own mental model for exactly what this thing needs to look like. That, that's, uh, I think a really cool insight.

Well, and I, I think you're really onto something with that, that idea of like the difference that can come from different macroeconomic conditions and the differences in the business. And I actually find it to be when we get candidates who come in, for leadership roles or other, and they're like, oh no, I know exactly what to do. I've got the playbook. I'm going to tell you, like, I did it here and I'm going to do the exact same thing here. That is a huge red flag for me because it just ignores that there are so many wildcards in every business, in every situation, and that the market is completely different than it was 2 years ago, 5 years ago, 10 years ago. You've got to run a different playbook now. And if you come in and try to take the playbook, even from another company that was like wildly successful, the chances that it's actually gonna work for you in the second business are not high. Like the same playbook just can't be applied in that way. So, you know, for me, one of the big unlocks in understanding how to approach that was, uh, my mentor at Twilio, George Hu, he was our COO. He came from Salesforce. He was like Benioff's right-hand guy. One of the questions I asked him, because his first marketing job had been CMO of Salesforce, and I just like could not wrap my brain around that of like, how do you approach a situation like that? And he really talked me through this idea of you come into a new role, one, people just wanna know where to focus. So like, give folks priorities. It's gonna be wrong. You're gonna iterate on it. That's okay. Like, just pick a direction. Any direction is better than no direction. And two, the other thing I saw him do was like pick up the phone and call other people for advice all the time. And that's the thing that I have come to realize that executives do is you're not expected to know everything. No one knows everything. No one knows what to do every time. So, when I get stuck, I pick up the phone and I call other CROs, CMOs, CEOs. And I ask them, what are you seeing? What are you doing about it? How do you think about this problem? And like that collective knowledge sharing is really like what unlocks things for me often. And it, it comes from that network of, of other great leaders.

Yeah, very much agree. It's, it's such a superpower. And I'm trying to bring a little scale to that to provide now some sort of a roadmap or a map for CROs to follow to figure some of these things out. Hence why I like to go deep on one topic so that people can pull these episodes off the shelf and be like, all right, how the heck should I operate a big team at scale? Or with Dini Mehta, we talked about going multi-product. Anytime you're going multi-product, just listen to that episode. And so hopefully this can help. Okay. So let's transition into our focus area of today, which is how to scale execution both at a rep level. But I think more interestingly and less commonly discussed is how do you scale execution across managers? And I personally believe this is the single most important thing that a revenue leader can do. Our jobs are about systems engineering. I heard you say on Robert's podcast Execution is the only moat. So I feel like we see the world similarly there. So just to cue it up, because your business is very unique, well, Twilio and Vanta in the speed of scaling. So can you just talk about how fast those teams grew to give people a sense for and what your org looks like today?

Absolutely. So the Twilio experience was a really unique one. I joined when the company was about 500 people, but there was really a very minimal go-to-market team, maybe only 20 folks. And that's because that business started as truly self-service PLG. So that PLG motion, inbound self-serve via the website, uh, that really, uh, accounted for the first $200 million in ARR. So that's the point at which I joined, and I joined to help create the enterprise sales function there. Um, you know, at that point in time, there were— the only real enterprise customers of Twilio were like big tech scale-ups, Amazon, Netflix. There weren't a lot of traditional enterprise customers. So, I got to help build that team over the course of several years. We went from just having the tech scale-ups to 6 years later, we went from 500 people to 9,000 people globally, from $200 million in revenue to about $3.5 billion. And the enterprise line of business alone went from really just those tech scale-ups to $1 billion out of the $3.5 billion run rate. So it was a wild experience and run to add that many people, that many customers. You know, the Vanta experience has been, you know, equally fast, but quite different because everything we do is direct sales. So we have no PLG component. So I joined Vanta around, uh, like after the Series A, around about 180 people. Um, we have since scaled that up and we're now about 600 people. We announced earlier this year that we crossed the $100 million ARR threshold. And, you know, it's been incredibly fun to just watch the acceleration of revenue growth. And, you know, we're heading into the next year. We just raised our Series C. We had Sequoia triple down with us and a lot of fun folks join the round, Goldman Sachs and others. So, We've gone from really like a very early stage startup to a much later stage growth startup that is really in hypergrowth. So, you know, we expect to continue that over the next year. Scope of my team, I've got basically all of go-to-market with the exception of marketing. So, got the entire direct sales team, which we've got segmented into a velocity business focused on startups. We've then got an SMB and mid-market team, an enterprise organization. So, I've gotten to create enterprise out of the gate, which has been really fun and didn't exist here before. I also have our post-sales organization, and I've taken that through a real transformation. It is now customer success and account management split into two. Tackled that side of the world. We've put a lot of work into net retention, which has been really fun. Um, probably one of the most enjoyable and rewarding, uh, challenges has been like, how do you, uh, increase net retention? Uh, which is, I know, something a lot of revenue leaders are focused on right now. And, and we've had a, a lot of success doing that. And then I've got RevOps and SDR, SEs, and, uh, it's a global organization as well. So offices in San Francisco, New York, Dublin, London, and Sydney today. I'm actually getting on a plane to our Sydney office here in just a few hours, and it's a, it's a great global crew. So, my team today is almost 300, so almost half of the company globally.

Okay. And what was it on the day you started?

On the day I started, I just had North American sales on day 1. So, I had a team of like 30. So, my team has 10x'd, you know? It's increased a little bit.

Okay, awesome. I want to— maybe we can come back to the CS and account management topic as we talk about scaling execution, because I'm sure that was an endeavor. So maybe just explain to folks what you mean by execution is the only moat.

Yeah. So, you know, we are at this point where we've seen such an acceleration in people's ability to ship great products, you know, the advent of AI, like you can ship a really powerful product pretty quickly. And, you know, as we saw with Vanta, lots of folks went out and tried to, to build copies of that product. And, uh, certainly nobody was able to, uh, do that fully successfully. Like, the product has continued to, to lag behind ours. But the truth is, like, buyers have a hard time differentiating, um, great product from less than great product. You know, it's, especially when you get into technical sales, you're dealing with platforms that are quite deep. So, the differences in products may not manifest until months after you've bought the product. It may be hard for somebody to grok at the beginning of a sales cycle because it's deeply technical and, you know, they're trying to run a relatively efficient buying process. So, you end up in this situation.

Not everybody is fully transparent.

Very true. Not everybody is fully transparent. You know, that is one thing that compelled me when joining Vanta was like highly transparent team and leader. But it's true. Like there's a, you know, there's a lot of marketing layered on top of lots of folks' sales cycles. So, kind of working in these murky waters where even if your product is truly the best product, getting buyers there to understand that can be quite hard. And like, I view that deeply as, uh, my team's job is really expose the truth and the reality that we've got the strongest product, and then simply create a better prospect and customer experience. And I deeply believe if we do that and we do it repeatedly and we do it at scale, we will win. We know we've got the best product, we're innovating faster. If it was that simple, I wish it was that simple that the best product always wins. It's not always the case. Like, it really does take a go-to-market effort to create a great differentiated experience that centers the prospect, centers the customer. If you can do that, to me, that is that moat that will create the win. And without that, you end up with a pretty murky marketplace where people are just kind of relying on, you know, limited information and often making decisions based on what looks shinier from the outside. So that execution is the key.

And growth can be sporadic and less predictable and all the things we really—

Yes. Yes. That is the thing that terrifies a CRO the most is the idea of unpredictable growth. You know, I tell my sales leaders often that I would rather that they are accurate rather than trying to paint a shiny picture of a positive outcome that's not actually going to happen. Like, I don't want to be lied to in forecast and given a rosy picture and told they're going to make the number. Like, if they're not going to make the number, I'd rather I have an accurate story from them and that we've got a predictable business where We tell you what's going to happen. That's what happens. And then we iterate and improve with every cycle.

I always tell people, give me the forecast that if you got within $10,000 on either side, you got double commission. Now, what's that number? That's the accuracy number. Don't give me the upside best case. You never know.

No. No, I like the range. I want to know your commit, which give me that as your worst case. That is like, even if everything falls apart, what's the worst case scenario? Give me your best case, which is your true outlier. Like if everything fell into place and you got as lucky as could be, what's the best case? And then give me your most likely, and that is truly your accuracy number. This is what I deeply believe my outcome is going to be. And if I had to stake my commission on it, what number I would call. And that way I've got that full range to operate within, and it helps them frame up how to think about those numbers and what level of confidence should go into each. Yeah.

Nice. That'll be a good example when we talk about frontline execution. But just more generally, what are the pillars to you of great execution? What are the things that you need to have built in the organization's systems rhythms, like how do you think about the, the system you need to build?

Yeah, I really think that there are, there are kind of like 3 key components here to having a great system that works, and the details can vary quite a lot. And like, you don't actually have to have a tremendous amount of infrastructure or systems. Like, you can do this in a really simple machined way, but You know, number one is you need to know with extreme clarity what the goal is. And that can be a little deceptive because I think people think of like, oh, well, we've got like a revenue target for the year and that's the goal. But I actually think it, it has to be something a little bit different than that. You know, in, in many companies that are growth stage companies like mine, the goal, the north star will be like, a growth, a year-over-year growth percentage. A lot of companies have that. And, you know, that really comes back to like investor perception, what you're trying to accomplish in terms of how you think about like the next several years of the company, what you're trying to prove. So, I think everybody in the company has to understand what is that north star thing with a number attached that we are trying to achieve and why have we selected that number. And that has to be your organizing force for everything you do because that's that North Star metric that's going to propel you forward. If you get lost, you get stuck, you've got problems in the business, you just have to reorient around that North Star. So, the North Star is one. Everybody's got to be aligned around it. And then, you know, the second piece you've got to have is the, like, how you work. And I deeply believe that you've got to have this foundation that's focused on the activities and the inputs. Like in sales, we get very focused on the outputs, and obviously the output is what matters, but the output you don't have total control over. What you do have control over is how you run your sales cycles, how you measure things, the way you operate. And, you know, at Vanta, we've implemented, implemented a value-based selling framework. You know, we use MedPic for discovery. We've got this framework that describes when you're running your cycle, how do you talk about the product? How do you anchor value for the customer? And how does that relate back to our offering? And then we've got, you know, a methodology for discovery. So that is that foundational framework, and you need everybody using that same framework. Framework, you need your managers inspecting that their team is actually using it and then like encouraging them to continue to go deeper into their deals using that framework as the guide. So that like how we operate is fundamental. And then once you've got your North Star metric and you've got how you operate, then it comes back to a rock-solid operating cadence. And the way I like to describe this is you're trying to build a learning machine. You know, there, you will never have execution that is perfect. Like, there will always be, like, you'll have talent issues, you'll have folks that haven't fully adopted the framework, you'll have macroeconomic conditions, you'll have things that go wrong, you'll have people that have to go on leave. You're dealing with a hu— a bunch of human beings. Like, stuff will happen. If you build a machine with a rock-solid operating cadence where, you know, at the foundation, you can think of this as like the forecast call is like the, the, the, fundamental element of this operating cadence, but it's bigger than that, where your team gets together on a regular basis, preferably weekly. You've got a mechanism to inspect the same metrics in the business and troubleshoot, like, where are we? What do we need to do next? What don't we know? And then learn and iterate. If you can build that learning machine and you build it around the how we work and the north star metric, That's really the whole ballgame. And building that machine effectively is the key to building an organization that can truly scale.

And so when you say learning machine, this is a manager's ability to learn about the deals and inputs. Is this about you learning about what's going on? Just unpack that a touch.

All of that. It is essentially an operating system for your organization that allows everyone at every level to inspect the way we're working the deals, the way we're operating, um, at a micro level, diagnose what's going on, like, and find patterns. And these can be patterns of things that are going well that you want to double down on. They can be patterns of things that aren't going well. It can be diagnosing risks, but it is fundamentally understanding why is what's happening happening, and then creating a mechanism to take action on that. So for me, like the simplest version of this is you run a weekly forecast call. That weekly forecast call shouldn't just be like a status readout. Like it should be a deep inspection of your deals, your business, your key KPIs. You know, in my forecast, we look at what are, what are our win rates, win rates by competitor. We're looking at conversion by stage of the funnel. Then we're doing like deep deal inspection on top deals and we're inspecting using MedPic. Like, what do we know about this deal? What are the risks to it closing? And through that process of group inspection, we're uncovering all sorts of things. Like sometimes they're good, sometimes they're bad. We take those away, and then we make an action plan to address them. We come back next week, and I've got action items, ops has action items, managers have action items. We all learn. We try to come back and do better the next time. And if you just keep doing that every week, you will figure things out. That's why there's, like, no magic playbook to tell you how to do it. But if every week you learn what needs to be improved, You improve 1% every week. That is the magic behind it.

Yeah. And that learning organization is really how a company becomes antifragile. No matter what's happening in the market or competitors doing things or regulatory change, if your company can understand, see, respond faster than your competitors, you win.

Absolutely.

I really like that framing. And it seems like the learning engine at the manager is about learning about the deals, and then at the director level, it's learning about sort of a bigger set of trends. And then you're really looking at the top, the top type of metrics and trying to cut the funnel by as many.

Yeah, exactly. And, you know, sometimes it takes time to even get to, like, what, what are the metrics as a baseline? And then you set a baseline and, and sometimes the discussion even becomes like, we'll look at a metric and it's not even about like, how do we improve it 1%? Sometimes like, is that even the right number? Like, what would it take for us to 2x that, to 10x that? And we use that as a mechanism to drive the conversation around like, how could we change the way we operate? Like, what if we completely broke the mold? And didn't take the current numbers as like the assumed baseline? What if we wanted to, to double it? What if we wanted to double our win rate against X competitor? What, how would we do that? So sometimes it's very iterative. Sometimes it's more like mold breaking like that of like, if we wanted to just break the benchmarks completely, there's always a way to do it. Like what, what would it take? And we use that discussion and that operating cadence as the place to do it. And so I run a weekly forecast like that. I've also introduced these quarterly QBRs, and in the QBRs, a lot of what we're doing is talking about those macro trends of like what's working and not working. How can we break some of those bigger trends or double down on them? And that's led us to make major changes in the business that have been incredibly positive. And then, you know, we learn, we come back again and we, we reset and that process of inspection really drives it. Cool.

And how clearly is this documented? Because, you know, the one question I wrote down is, okay, so managers need to inspect, but how do you make sure the managers are inspecting the right way? So what's the system to try to get that consistency across VP, director, manager, all the way down to rep? And how do you as a CRO know that it's being done or not being done?

You know, a lot of it is like spot checking. So the how I know it's being done is within my operating cadence, I've got opportunities to spot check. And I know I've got these touch points where I can go super deep to drill into, like, we'll drill into individual deals in, in my forecast. And part of why I do that, yeah, it's about like checking into the deal, but it's also about spot checking. Like, is this deal being run in the correct manner? And if I inspect enough deals, I can identify patterns all the way down to my frontline to say like, oh, there's like a whole practice missing in this part of the org where the manager isn't doing the thing I need them to be doing. So, ideally, yes, that is all documented and written down. Generally, what I find is, like, we have created great manager playbooks. We've got, like, really clean documentation at our frontline level. Our second-line level is relatively new. So, as a growing organization, we've only recently sort of added that second line. So, that's now where we're starting to add more documentation. And, you know, as I look at my org over the next year, I'm going to be introducing a number of second-line leadership roles. And once we get a little deeper into that, we've got more scale there, we'll likely have a more documented playbook. That'll be kind of our evolving edge of the organization, and that'll get written down. And then we do, you know, I work with my RevOps partners very closely. They are the single most important org for me. They're like my right hand, my head of RevOps. I probably talk to him more than anybody else in my life. And, you know, you're here. Yeah, he's a total bestie. Mark Lail, shout out. And Lail's team, he's got a— we've got a head of operations, Kyle Piercy, who's phenomenal. Like, these guys, I talk to them constantly, and they, with me, are really the ones owning this operating rhythm. So, you know, on basically quarterly basis, we get back together and re-document what that rhythm is. We rethink, like, are we inspecting the right things. We rework the way we're doing the forecast. It's like, what's our opportunity to go deeper now that the business is bigger? But they really help drive the structure around that and the documentation around it.

Very cool. And so a manager will have like a fully laid out, this is how you run a forecast call. These are the questions that, that's in a training as well.

That's exactly right. That's exactly right. And you know what I find is, Absolutely, you can train managers to do that. It's also a mindset. So, you got to make sure you've got the right folks who have that level of urgency and really want to adopt those frameworks. So, getting the right talent, getting the right leaders on your team is just as important as the training aspects of, like, having the playbook and showing them what you need them to do.

Awesome. Yeah. Couldn't agree more. We're a stage behind. I am on a on a mission to document everything a manager does and be way more explicit than we are today about what does good look like there. So it's cool to see that you guys have come out the other side of it and that we're on the right track. So we talked learning machine. Any other key parts of this operating rhythm that give you the insight you need to make great decisions, like things that you've built that you're like, I wish we had that a couple quarters before. And going back to this idea of being able to like grok the levers.

Yeah, I mean, the math is truly at the heart of it, and this is something I'm really passionate about, is like, you know, at the heart of this practice is math, and it starts with the North Star metric. You need to then, of course, understand your secondary metrics and what you're driving towards. And, you know, for a lot of businesses, your North Star metric is going to be your top line revenue growth. Your secondary metric is very likely to be net retention. You know, law of big numbers, the bigger a business gets, you really need that net retention to be driving your growth in addition to new logo revenue growth. So, you know, once you've got those established, you've got to have clarity down to the penny and down to the point of what your expectations are of how you're going to get there. I think that a lot of— I work with a lot of early-stage founders and it's super fun. Um, and a lot of what they enter thinking is you just sort of like make great product and then you hire some salespeople and you go sell. But the truth is like there's just so much math behind a predictable model. So, you know, we now have a model down to the penny that predicts everything from You know, how productive our salespeople are going to be to what conversion needs to be at every stage for a lead moving through the funnel, down to what percentage of our pipeline is coming from what sources and what the CAC is going to be for each of those. So, like, we take that math as the basis for our inspection, and we're then measuring against it. And it's, it's okay if it deviates, but the key is understanding why it its deviation, and then yeah, you just iterate from there. So, you know, this year is a great example for us. We identified a completely new lead source this year, which is very rare and hard to do. Very lucky. So identified a great new lead source and, you know, next year we'll build that into the model. And now the discussion is, okay, we've got this new lead source. How do we like 2x that or 10x that? Like, how does that become a real part of the business? So, like, having the math and the assumptions is what allows you to do that deep inspection. And, you know, I find some of our most important week-to-week metrics on that front are going to be average contract value by segment is incredibly important. Win rate is incredibly important. We look at that by segment and by competitor. We're just, that's, those are things we're looking at every single week. And when they move up, when they move down, it's just about understanding why, so we can then go figure out what to do about it. And, uh, you know, then we've got this extended set of metrics that we look at on a, a less regular basis.

Hmm. So you look at those every week?

Yes.

Okay.

Every week.

How many key assumptions are in that weekly audit?

Quite a few. So, and it's, we've extended the number of metrics that are going into that weekly view. You know, we, I'd say The goal is to continue to extend it. You don't want to get into analysis paralysis. So, that's the other trade-off is you want to make sure that the metrics you look at every week are actually ones that really matter and that are actionable. So, you know, we're always walking that fine line of like, let's look at the stuff that really matters, not too little, not too much. We find that, you know, things like contract value and win rate, um, time to close is another one that I find to be very important. These, because we have a very competitive landscape, those numbers move up, they move down, um, pretty frequently. And the faster we can action it, the more successful we are encountering, um, any kind of downward trend. So, you know, we, I would, I couldn't even tell you how many metrics we look at weekly and forecast best guess now, but I will say, like, I want to say we, you know, have, we have Tableau infrastructure set up where we're basically looking at a key set of dashboards and we're looking at dozens of different metrics. And with each iteration, we're trying to get more precise. So we're not necessarily looking at the business overall anymore. We're looking at like our business selling to startups and we're looking at our business selling into SMBs and selling into the mid-market. And like with every iteration, we're getting more precise in how we look at those assumptions.

Yeah. And I think a lot of revenue leaders listening to this could easily get overwhelmed, like, well, that's Vanta. They're like this. They've got the product, the resources, the this, the that. And my advice commonly to people starting out is just like, just get started. Just put 3 metrics in a spreadsheet or a dashboard that are the most important ones. It could just be pipeline generated win rates and then pick something else and that could be enough. And every month we're in a transactional business. So we do monthly business reviews instead of quarterly. But every month that MBR pack, our red, yellow, green chart gets a little bigger, a little bigger. and we get more refined. The feedback that hopefully people can take is you don't need to get there out of the gate.

Absolutely not. Yeah. It is like the starting is the key. We were talking about this yesterday. We, 2 and a half years ago when I joined, we didn't have forecast calls. There were no forecast calls. Wow. Okay. Yeah. So there were not forecast calls. You know, when I joined, I said, what's the churn rate? And I think ops went into a panic. And they're like, I'm not sure what calculate that? Like, give us a few days. So, you know, there was a lot of, you know, infrastructure missing there. And we started very simple and it really was like, can we literally get on a call together and call a forecast number, single number, and like, can we just start there? And then can we start to measure accuracy? And then can we start to get into a little bit more of the like, KPIs and the causation. So, yeah, that iteration is everything. Your first go at it, it will be rough, and that is okay. That tells you you're on the right path. Like, get uncomfortable, do, do the thing, even if it's one metric, and you will learn what you need to add to the picture as you go.

Yeah, I, I have gotten obsessed with product management over the last 5 or 6 years. When you are a revenue person at Shopify, you quickly understand the hierarchy. And so in order to be taken seriously, I'm like, I need to learn how to speak product. And in doing so, I discovered, I was like, oh my Lord, this is the best framework to look at anything, building a revenue team, building a business. And one of the things that I try to impress upon people is just the bias to action and then the need to ship something to get feedback. And so, if it's a dashboard or an MBR, it's, oh, we don't really have time for an MBR. Just put the hour on the calendar. You can all just pile into the meeting and open up dashboards randomly. It can be that hack. But just by starting that process of building a habit, you're going to feel the need to iterate and improve. It's just about, like, doing the thing.

It absolutely is. And if you do it together as a group, I find that to be the key. It's like one thing to do that in isolation as an individual, but like bringing the team together to all sit together and look at those numbers, like there's something in that practice where discussion emerges, you start to learn together, and then you figure out like, oh, what's the next metric? And like, what does this tell us? And then what do we not know based on that? And then you start to build into this much more complex structure that evolves over time. But it takes that practice of doing it with other people and that group learning together and iterating into something more complex.

I can't remember what podcast it was, but I heard you recommend to founders, even for early reps, just bring them into anything. It could be an investor conversation, just the context. The context will help them level up, which I think is a great approach. Like, if you don't have it documented in systems, just bring them in the room.

You know, let them see everything. You know, we talk a lot about this idea of at-bats and just having the at-bats to learn. Like, you can train people and it's great if you've got like a training course and you kind of put your reps or whoever through it. But like, it's extra true early stage, but it's true at every stage of a business. The more at-bats your team can get, the more conversations they can hear, the quicker they're going to learn because they're learning from what real conversations sound like. So, it is glorious that we're in the age of Gong and like you've got call recordings and you can hear more things now than you could in the past. But like, yeah, bring them into everything. Like it's really your goal should be, especially for early stage, to have your salespeople able to speak as if they are a founder of the company. You want them to talk with that level of confidence. You know, I was, I posted something yesterday about like, I don't think there are any real magic tricks in sales. I think it is like very simple, honestly. And a lot of it comes down to curiosity, great discovery, and then it comes down to confidence. It's just like the confidence to come in the room and like, You know, we talk about this when it comes to value selling, but like being audible ready, being able to like speak to things comfortably, not from a script, but from deep knowledge and understanding that comes from hearing lots of conversations. That is the magic. And if you can get to that place of comfort through hearing all those conversations, you just are so much more successful.

Yeah. Yeah. And so what else? This is a good transition to talk about how do you scale this across multiple levels of leadership now? So in the early days, it's just get people in the room, get people at bats. That's obviously harder when your team's 300 people. How do you scale your values, the approach you want to take to stuff? Because obviously you've got a strong opinion about this rock-solid operating cadence. So What are the ways that you're scaling this across the organization? We, we've talked documentation, getting in the room. What, what else is in there?

At the end of the day, truthfully, you've gotta have the right people at all layers of leadership, and you've gotta have folks that are bought into the methodology, they're bought into the operating cadence, and they can help enforce it. So, my piece of advice, number one, as you're doing that, it's like, don't settle if you've got managers or folks on your team who don't understand the way you're trying to run the business, the team under them will be unfixable. Like, it is not, you can't fix the structure if you've got a layer of that structure that isn't enforcing the operating cadence and like trying to make it real. So, you gotta have great people, be willing to make change on that front and bring in people who are bought in on the methodology and who have the urgency. In seat. So, if you've got those great people in seat, then it's about creating not just clear expectations, that's sort of table stakes, but also starting to give exposure to each layer to understand the problems that the next layer up are trying to solve. So, for example, I've got a VP of sales and partnerships and he's phenomenal, Elliot Goldwater, great guy. You know, it's his first time in a role like this, one thing I often am trying to do for him is expose him to the way I'm thinking about the problems I have to solve. So, the way I am interacting with the board or the leadership team, and I'm really trying to give him a glimpse into, like, what are the problems that I'm trying to address in the business? Because that helps frame how he runs his team and how he starts to prioritize in his business. We do the same with frontline leaders. We've got great frontline leaders. And one thing we love to do is once they're comfortable doing the job is we'll bring them into the one layer up. They'll come to my forecast meeting instead of just running their own for Elliot so they can start to see, like, what are the questions I'm asking him? What is his job? What are the problems he's trying to solve? So sometimes it's just about giving them a little bit more visibility to the next next layer of priorities and challenges. And that sets the context for them to learn and understand, like, what role does their team play? What role does the framework we've given them play in the bigger picture of the business? If you can create that, you start to have a team that really understands, like, not just what we expect of them, but like why and how it fits into what we're trying to accomplish as a bigger team.

I really like that. That's a good prompt for me personally to try to do more of that with my team. That's an awesome takeaway. I want to quickly touch on strategy. So as a part of this whole rhythm, you've inspected, you've found opportunities. How do you think about prioritization? Do you have a framework for your team to understand what you're taking on? What resources get put behind it? How are you, how are you managing those trade-offs?

Yeah, a lot of it comes back to the North Star. You know, we, we run our team based on math. That math stays consistent every year. If we're going to make a change to that math, it is like a huge deal. And like all of us are engaged in that. That's even beyond our team. So we're all clear on that North Star of what we're trying to accomplish. So basically, as we, make our progress through the year, we learn, we iterate, whether we see an opportunity or we want to make a change to counter a negative trend, everything we do gets tied back to that North Star metric. So, you know, when my team brings me things, often what I will ask them is sort of like, how does this tie back to growth? Like, how does this ladder back to our our North Star metric for the year. And if it doesn't, frankly, it's rarely going to get prioritized. You know, the one exception to that will be with my more senior leaders. We are looking at a longer time horizon. So, we want the majority of our team focused on the 12 months we're in. We are also a very high-velocity business. We're bringing in hundreds of customers a month and it's all direct sales-led. And so, we close every single month. We don't do a quarterly close. We do a monthly close. And so, you know, I want most my team thinking not even just about the year. I want them thinking about like the quarter and the month. My more senior leaders, I do want them thinking on like a 24-month or even a 36-month time horizon. So there are exceptions where we will orient around the, like, OK, we know that here's our goal this year. We also know next year, we need to deliver similar kind of growth. And this is an investment we need to make in the current year to make next year possible. But like all the decisions we make still fundamentally come back to the math, the growth rate, and those North Star goals. And if they're not on that list, frankly, they typically don't get prioritized.

Makes sense. So let's talk about behavior change. So as a— your operating cadence is delivering insights, opportunities to get better. It matches with your math. And your North Star. Now you have to get a bunch of people to change what they do, which I think is arguably the hardest part of what we do is, you know, it's way easier to get in a spreadsheet, build a great plan, but the rubber meets the road when it comes to how do you get a manager to actually do something different after they've been doing it the same way for quarters or years.

Yeah.

And so you talked about this CS and account management change, so maybe we can share some stories from that. But how do you lead people through change? What are the big pillars for you to drive behavior change across an organization?

Yeah, I mean, this is truly one of the hardest things. You know, people get comfortable doing something, and it's particularly hard, and this is counterintuitive, but it's actually even harder when the business is doing exceptionally well to make change because What I'm doing is working. Like, why are you asking me to do something different? Like, I'm crushing my quota, things are going great. And that can sort of be the curse of success is like there's more resistance to change in a lot of ways. But, you know, the truth is every business as it grows and scales has to undergo change because the numbers get so much bigger. The way you operate does have to change. So to do that, I find a couple of things are really important. One is just like overcommunicating that information. It's not just like, what is the change expected, but how does it relate back to the big picture and why are we doing it? You gotta communicate what's in it for the person making the change. So, like, it's great if the answer is we're making the change because we think it's gonna lead to more growth, but like that individual might not care that much about that because they're kind of like, I've got a quota, I'm doing my thing. You know, outbound is a great example of this. Like every business that scales, you end up having to become an organization that builds an outbound muscle. You should expect that every AE is going to have to source more of their own pipeline. And when you've got a team that's like hitting their numbers and you start telling them, I now expect you to dial up outbound, sometimes you'll get that like, uh, why should I do that? Like, I am doing great. Like, why are you wasting my time? Isn't that an SDR's job? And you get kind of this pushback. And, you know, so communicating to them what's in it for them. In the case of outbound, maybe that story is, hey, like, we've got a couple people on the team who are outbounding at this level, and here is their attainment. And you can see that, like, they are more successful, they are making more money. So, like, bringing it home and personalizing it is a second piece. And then you just have to have the reinforcing mechanisms. So, like, having the systems and the processes that reinforce those best practices is super important. And the other, like, less comfortable part of that is you have to set hard boundaries around it. So, if folks aren't willing to make the change, you have to be willing to part ways with them. And that can be really hard as an organization matures because you can have folks who, you know, are doing incredibly well one year and the organization changes over 2 or 3 years, the expectations are different, And if they're not able or willing to embrace that, you've got to be able to say, like, the bar is now here. I appreciate it's in a different place than it was 2 or 3 years ago. And if you don't meet that bar, there is not space in the org for you because we are a different team now. And, you know, I think you got to have that conversation compassionately, but set a firm line because the thing that will kill any organization and like any change is if you say it, but don't mean it, or say it, but don't enforce it. You know, if people see that it's flexible or that like you're saying it, but like there's really no ramifications for not doing it, you're not going to get the adoption. So, you got to be serious. You got to follow through and you got to get the right combination of like carrot and stick to make it worth people's while so they care, but also so they understand it's not optional.

That makes a ton of sense. A framework that gone back to a bunch. I've got young kids. I know your daughter's older, but there's an author, her name's Dr. Becky, and she talks about sturdy leadership and loving boundaries. And it's just language that's rattling around in my head because I have a 2.5-year-old and a 4.5-year-old and setting those same— it talks about the importance, like kids want boundaries. And I think everybody wants some sort of boundary so they don't feel like it's chaos. And, if you deploy a change and you're not that serious about it, you don't have the reinforcement or carrots and sticks, then it's hard as an individual contributor to know what's important, what do I actually action? And, that's honestly more stressful and anxiety-inducing than anything. Yeah.

Well, especially for the folks who are actually doing the change, making the change, like they start doing the thing, which in many cases you're asking them to do, and it's difficult and it takes extra effort. And if they see that there are others who are not embracing the change and it's tolerated, you end up with this situation where your folks who are your top performers who are doing what you're asking them to do become resentful because Yeah, they're doing more and then they're seeing that like it doesn't actually matter and there's no consequence for not doing that. So you got to get that balance right. And I think boundaries are exactly the right way to articulate that. You just need clear boundaries. You need clear expectations. And then you also have to have an appropriate amount of recognition. You know, one thing we ended up building that was super helpful was we called the balanced scorecard. And the idea behind this balanced scorecard was to help the team be recognized for more than just hitting quota, because the team was frankly doing so well that we had a little bit of this like, well, why would I outbound? Or like, why would I focus on increasing my deal size? Like, I'm hitting my quota. Isn't that like you want? So, we created a balanced scorecard that takes into account, um, your attainment versus quota. Plus 5 other things that we think are really important. And that includes your average deal size, it includes your win rate, and it includes the number of outbound opportunities you created. And that was turned into a leaderboard that we published to the whole team. So, you can be on the top of the leaderboard by doing those right things, even if you're not the top quote, attainer, because what we're trying to drive is these behaviors that we know drive growth over years and that we know with consistency drive success. So that scorecard and that leaderboard have been pretty transformative for our team in understanding exactly what we expect of them beyond just hitting their number.

Yeah, that's great. We do that at a leadership level. We, we run a similar exercise and we stack rank every rep every single month to understand Okay, who's getting to their number, but who's doing it in a way that's durable? You've said who's doing it with a party trick versus what is more sustainable. And so I think that's a great way to look at it because there is business value to outbound. There's business value to hitting your number with a higher win rate because you're taking less opportunities. Those things are valuable. If you're a rep that just brute forces their number, with low win rates, but just like effort. Yeah, it's great. I don't want to diminish it, but not as valuable from an efficiency or a scale perspective.

Yeah. And it's certainly just a little less durable. And there will go with all of those approaches, they can work for a period of time, but with a business that is in hypergrowth, that's undergoing so much change, they run out of runway. So the goal is really to expose the behaviors we believe are leading to durable success over years, and then really reward and encourage those. So that leaderboard for us, we expose it to the whole team. So everybody can see where they are on the leaderboard. And there's that sort of social pressure and like the clear understanding of what we expect, who's doing it well. And that also sets those folks who are at the top of the leaderboard up to be leaders on the team and to share what they're doing that's working and like We want that. Yes, it's pressure, especially for folks lower on the list, but it's also a way to really recognize the people that are, are doing those things well. And we celebrate those folks. We ask them to share what they're doing and like train their peers. And so there's a lot of prestige that comes with being on the top of that list.

Yeah, that's awesome. We've baked this into our promotion framework. There's metrics, skills, habits, character, business need. That's how you get promoted here. Metrics are important, but are you doing it with craft? Are you demonstrating the skills? Are you doing it with the right habits? Because every role is harder than the one before it. And if you've gotten by but your time management habits are bad, if you're riding this crazy roller coaster of emotion every month, that would be a habit that we get nervous about because if you're riding the roller coaster as a BDR, oh boy, it's not going to get better as an AE. So, that's our version of it. But, I think publishing something like this could be helpful. And, I had a rep who was one of the top performers, but it was party trick driven. I shared this feedback with him, didn't take it all that well, and we promoted somebody else because these were the things that were more durable. And ultimately the party trick rep ended up petering out because that thing wasn't sustainable. And, but it's hard, it's hard to get people to understand that. And ultimately, if it's not a fit, it's not a fit.

Well, and I think you're right to weave it into the promotion framework. Like you want it to be consistently woven into everything you do because then people start to understand it. They understand that it's not just like a dashboard you flashed up once, like it's foundational to what you're looking for and what will drive success in the business. And that's how you get real behavior change over time. It's not like, here's this one thing this one time, or like something we bring up maybe once a week. Like, it's foundational. And like, that is what we believe great looks like. And the folks that you want on your team, they will conform to it because they want to succeed. They want, they want that OTE to grow, to, to grow. They want to like level up And so, you just have to shine the light for them on what it looks like. And then you end up with folks who really do want to climb the leaderboard. And you want that team who's like aggressive and competitive. And, you know, we, I think we've got a very friendly team. Like we've got a very collegial environment. So, I think we're striking that right balance of extremely aggressive, competitive, but also super friendly and supportive. And, you know, we've got a couple of reps who are often, you know, near the top of the leaderboard. That come to mind in particular who are, who have become so close and they both root for each other and they also try to beat each other constantly. And like that healthy competition has been amazing and it, it really allows people to break out of the mindset. And we've also got a rep this month who he's been with us for several years now and he's been a solid performer. And as he's gotten this clarity around what great looks like and he's working with a really solid manager, He started to challenge himself and like, I think that he maybe thought he wasn't capable of some of these things. And all of a sudden he broke out of that mindset. He's going to try to do, and he's on the path to potentially do 4 times his quota this month, which is, it would be a company record. It would be. Yeah. He's like, he's on this incredible tear. I believe as of today, he's already at 2x quota. And we're on day 10 of the month. We run a monthly, a monthly quota.

Yeah.

And, uh, you know, there's just something about that. Like when you shine a light on it, it's aspirational. You celebrate, like people break out of the box and like anybody can reach for that. And, uh, to see somebody doing that right now is, uh, is really cool.

That's the most fun. Just that person finding that extra gear and, and, you know, really understanding it's like, why not me? Like, let's do something extreme. Yeah, I love hearing that. The term that gets thrown around a lot is like coopetition. Like, you're a competitive team but really cooperative. We've got a similarly built culture here, which is such a benefit. Anything else around systems to reinforce? So, we talked about leaderboards, recognition, consistently woven into anything. Anything else there, maybe on the data or infrastructure side that you want to highlight?

Yeah, I mean, the data— having the data easily accessible has got to be like step one of that. Like, everybody's got to have the data that they need. I deeply believe the future of all of this is much more like elegantly integrated systems that have been unsiloed. You know, I'm making a big investment now in, um, AI-powered workflows and And there's a lot out there. You know, the traditional revenue stack is still an extremely siloed revenue stack. You've got all these tools that are not well integrated. I think there's a massive opportunity to create an elegantly integrated revenue tech stack that serves your sales team the right information when they need it, makes them super effective, and then serves up insights as well. So, we're doing a really nice job of this through a combination of systems and humans right now. But my bet over the next 24 months is that like doubling down on AI-powered workflows and the power within like that artificial intelligence is really going to take it to the next level because we've got these incredible humans doing great work. If the machines can reinforce that work really cleanly, I think there is a next level of efficiency that we can unlock and next level of success we're gonna be able to unlock. So, I'm, I'm a real believer that like AI is not here to replace the humans, but it is truly augmentation. And if we can augment our crew, uh, with great data and great insights, right, right thing at the right time, I think we can really change the trajectory of our success.

Totally agree. We are on a very similar path right now, just trying to automate and enrich and do as much of that as possible. In your conversation with Scott, you mentioned you were just hiring these AI specialists. Did you end up putting those folks into RevOps, like dedicated AI workflow people?

So we're, we're on that journey now. So we've got some folks who are dedicated. Next year, the goal is to have like a fully dedicated team that's going to focus on that kind of AI work. Workflow optimization. We've brought in some great tooling and we've made some incredible progress here. So, you know, we, we're, I'd say we're early in that journey, but it's something that, like, one of my big lessons as a revenue leader is if you give everybody some, if you give everybody a job, it's nobody's job. And if you give somebody a side project, it'll never get done. So, like, the goal over the next year is to have a fully dedicated team that just owns workflow optimization and process optimization with AI at the heart of it. So we're going into annual planning as we speak. So wish me luck getting those requests approved.

That's a dream. I love that. Yeah, single-threaded ownership. It was a pillar of this presentation I gave at SaaStr, a SaaStr workshop. I couldn't agree more. What's the coolest thing you've done there in terms of workflow optimization?

Oh man. Well, we're doing something really cool right now with, uh, Clay, uh, which is a great tool that I'm really grateful to actually have invested in Clay. Um, I do a little bit of investing on the side with a group called 20 Sales. It's actually really fun. We've got a, a $5 million fund. It's 8 of us. We're all go-to-market operators. And, uh, it's been a blast. We get to work with early stage companies and help bring them go-to-market expertise and And so really grateful to have invested in Clay. It's just a very cool product platform that brings a combination of sort of AI-powered data enrichment and then AI-powered workflows. So we have built some really interesting workflows such that when you get an opportunity in, in our system, you can enrich it based on persona using Clay, and then that tees up some interesting workflows that are informed by that data that you've then enriched that opportunity and the account with. So, like, we've been able to build something that's really custom to our personas and, like, our buyers that is just super elegant and super clean. So, there's so much more we're hoping to do there, but, you know, we often sell to CISOs. And you know, the traditional experience here would be you've got an opportunity, you go hunt and peck and hunt down like contacts and, you know, like read, I'll read all the things. We have been able to build a lot of automation to just like elegantly deliver that. So, it's sort of a like enrich me and we've got a variety of personas and it'll pull in the, all the data enrichment for those personas in that account. It'll tell you which persona those people map to, give you all their contact info. And then it gives you workflows to take that information forward. So it's sort of a like account map in a box that is custom to our business. That's one thing that's been really transformative already, but we got a lot more coming there.

Super cool. That's awesome. I'm a big Clay believer. We ended up building a bunch of this in-house and like custom coding it because our buyer is super not online. Like we sell to restaurant owners, they're not on LinkedIn. A lot of the Clay stuff is built for a white-collar sales motion. But yeah, it's exciting. Okay. So let's transition to quickfire because we have— I think we're running out of time here. So what do you wish you knew in your role today back when you started? So CRO day one at Vanto, what do you wish you could tell yourself?

I wish that I had, uh, operated with better data sooner. Like, I think that when I look back at the mistakes I made in year one, a lot of it was rooted in not having the right data. And I knew that, but I settled for it because it was hard. And, you know, like, I didn't, didn't quite have the right resources to get the data I wanted. Like, I should not have settled that. Like, I should not have— I should have not made decisions until I had data I was confident in. And that is, you know, really like the, the ecosystems of mistakes in year one. Pretty much all of them come back to that. And it led me to make decisions about like where to invest that weren't quite right, led me to make decisions on like profiles around hiring and like reorientation of territories. Like, there were a bunch of decisions that I wish I could Go back and redo. And fundamentally, I could have made different decisions with better data. So like, get the data foundation in place, number one. And even if you can't build it out and it's not elegant and you don't have your team to deliver beautiful dashboards, like, there is always data in a business. Like, you gotta be comfortable going super deep and like pulling those pieces apart yourself, run your own reports and figure it out. Out. So data-heavy decision-making from the start should have been the MO.

That's awesome. What do you think separates a good CRO versus a great one, a truly elite one?

Hmm, you know, the— I think the great CROs are the ones who can actually move the metrics, and I think that's actually more rare than you think it might be. There are a lot of CROs out there who are doing a very competent job as like a operating the business, running forecasts, like gathering the information, you know, dialing up and down the normal stuff. But like, you've got to take it one level higher and understand from a board level, from an investor level, what is the company trying to accomplish on a longer scale? And then you've got to be able to orient your resources top to bottom to accomplish those goals. And if you can get in command of those levers, and truly redirect the resources of the business to accomplish those board-level goals, that to me is what great looks like.

Nice. What's the hardest lesson you've had to learn?

That sometimes you got to slow down to speed up, which I find very painful. You know, I have— I am a big bias for action. So, like, the, the frequent criticism I get that is incredibly fair is that sometimes I just move too fast, and that comes with either not fully communicating something or, like, making change too fast without taking everything into account. So, like, for me, the patience to slow down a little bit is one of the, the harder things that I continue to have to work on. Like, okay, it can wait one more day while I do a little more investigation. I can build a little more consensus. So, like, I'm still calibrating finding the right pace because I love to just go.

I'm trying to learn this lesson myself when it comes to deploying stuff. We, you know, we build it, we're like, go ship it, go, go. And we're really trying to just slow everything down. Comms, education, training, like it's, uh, it's a tough one. Doesn't come naturally.

It's part of what makes things durable, unfortunately. You know, you got to take the time.

Yeah. What's the best thing you've read in the last 12 months?

Oh, that's a great question. You know, I— best thing I've read. I always go back to the classics, which actually, you know, this is going to sound silly, but some of the most helpful things I've read in the last 12 months have been like benchmark reports and like the education that comes from some of those benchmark reports. And this is true in my role as CRO and also as an investor. Like, I truly have started to find that there are, there are a lot of garbage benchmark reports, but there are these like key benchmark reports out there in the world that will tell you so much about how other organizations are operating. And if you can get your hands on those, While there's not a textbook for the CRO, that is a little bit of the unlock of like, ah, I see what they're doing. Like, I see how these businesses are operating. So, like, great places to find those are, there are, um, like either PE firms or other like big venture funds that'll put out benchmarking reports. Look for those. Those are, uh, truly some of the best reading I've done in the last year.

99% of them are so bad, but you find a couple good ones and yeah.

Just so many nuggets once you find the right ones.

Yeah. Well, this was awesome, Stevie. I had a blast. I have just a whackload of notes and I think people are really going to take a lot away from this. Just the importance of being able to build this rigor, whether or not you're in an insane hypergrowth, Twilio or Vanta or something that's a little steadier. Being able to have this operational excellence and this discipline is just incredibly critical. So I think you've really given people so many tactical takeaways here. So appreciate you coming on.

Awesome. Thank you so much for having me. This has been really fun.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't Don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.