Inside Clay's Sales Playbook Scaling to $100M ARR

Thanks for having me.

So I have a lot of these types of conversations, both with peers and with folks that are having this kind of evaluation. And there’s two ways to approach it, right? A lot of folks that I talk to are at software companies. They’ve been there for like four years, five years. The learning curve is kind of flattened out. The phrase that I use to describe how they might feel is like, hey, do you feel like you’re kind of like rotting? Like you’re you’re not you’re not learning a ton more.

The learning curve is flattened for you. You’re not in an AI space, which like I think is like the next the next phase of things to learn. Almost every time they’re like, yeah, that’s exactly how I feel. And I’m like, okay, let’s let’s fix that then. Because once you stop learning, like, you actually, as a person, I think, start to settle, and then it’s just like a process of settling all the way down to the bottom.

gotta go find something else, right?

I mean, maybe you can move you can move into like a different role or like a different subsector of the company. But usually, like, if you’ve been there for four or five years, the company is pretty big. There’s a lot of structure. There’s a lot of process. There’s There’s not much more for you to innovate meaningfully. I mean, maybe you could go run the company’s VC fund or something, right? But at the end of the day, like, if you leave a company like that and you move to This is partially why I joined Clay, right?

If If you leave a company like that and you go to a next gen AI startup, you’re to learn way more. The surface area of what you can actually go and impact is much, much, higher. And I think that’s what those types of people are excited about, right? Like, if you’ve been at Salesforce for 12, 13, 14 years, like, you’ve probably had an incredible run. You probably really enjoy that and you’re probably gonna stay there. But like most people are at companies for like four or five years.

I don’t think it’s a bad read. I actually so we’re we’re recruiting a lot right now at Clay, and I see a lot of profiles. I actually ran a training for my team on on recruiting last last week, the week, before. And one of the things that we talked about is like, how do you read a LinkedIn profile?

Right. And just pulled up people’s LinkedIns. We pulled up yours. It was actually really weird. We’re like, don’t hire this guy. No, I’m kidding.

So we pull up LinkedIn profile and and I’d be like, okay. what do you like? What do you see that you like? What do you see that you don’t like? And it’s actually there’s a certain amount of time that if you spend at any company, it’s like kind of a red flag because it’s like, can you do something new? Can you operate outside of the bounds of what you’ve built and what you’ve done? Right?

There’s a lower bound too, and I think it’s two years, right? I was thinking

Yeah. I mean, I’ve spent the last decade at two companies. And I’ve built something, I’ve learned a ton. And when that learning curve starts to cap off, okay, you start to think about what’s next and what’s new. I think it’s probably like seven years, six to seven years. After that, if you’ve been in a company for eight, nine, 10 years, it’s like the company is kind built around you probably. And you you’ve built so much of it to like I don’t know the best way to describe it.

It’s like maybe like putting on someone else’s shoes. Now, like I to like, I don’t know, redo the laces and the insoles all, you know, screwed up. Like, I think it’s really tough for someone who’s been at a company that long to like adjust and and prove me wrong, right? Like, I have a friend who is at at Heap, which was at two companies ago, right? He was there for like eight or nine years. And actually, like, every time that, you know, the LinkedIn anniversary, it’s like,

your friend has been there for this many? I just, like, one year, I I screenshotted it. I sent it to him. I was like, yo, blink twice if you need me to save you. Because like, but he was like, look, I’m learning. And like, yes, there is an end date. There is an expiration date. But like when I see something like that, especially at a company like Salesforce, I’m like, okay, you you have your thing. You know what you’re doing. You probably have great hobbies outside of work.

That’s that

Well, actually, when I see that, I look at it and I’m like, okay, either you’re like, I don’t know, you’re at SCO, or the vast majority of them are are them speaking at a wedding and you can tell.

And then like, you know, look, I don’t know. I don’t know. I don’t have the perfect LinkedIn. I should probably invest way more in that. You know, everybody at Clay is like a social media star. I’m like actually very averse to that because I think that I’m like always terrified of saying something really stupid. like, you know, you look at my LinkedIn. Lucky you’re on

a podcast.

Yeah. Yeah. So yeah. great, great, great, job here. Right? But like, you know, I look at my LinkedIn, it’s like, I’m very critical of everybody else’s LinkedIn profiles. I’m the most critical of mine. I need to take a new LinkedIn picture. I have like a lazy eye in my picture and it really bothers me every time I look at it. So when I look at other people’s LinkedIn profiles, I’m like, God, what do they think about mine? But when I look at a LinkedIn profile, what’s a red flag?

Obviously jumping around. I always like, here are some of the other tips. Like, you discount recommendations. I don’t give a shit about how many recommendations I have, but some people do. Yep. I I just discount that.

Yeah. like, you know, people love to put like, oh, I was at President’s Club or like, here’s what I did on quota, right? That’s like a, that’s a green flag. I, when I look at someone’s LinkedIn and I can’t tell the story for them. So like, I’ll give an example. All All companies that like, I think are great, I love, but imagine you’re looking at someone’s profile and they’re like, yep, I did two years at Snowflake and then I did four years at Lattice and then I did three years at Marketo.

And you look at that and you’re like, this is kind of a mishmash of companies. So like, what’s the story? Where’s the expertise that you’re building?

A little bit. Like, think about there was a guy that worked for me. I actually think I gave you his contact info. His name’s John Dalton. Yeah. And we worked together. We built dbt, I mean, gosh, for four, four and a half years together. And if you look at his LinkedIn from the outside, you can see a very clear, I’m becoming the data, the early stage data sales expert. So like he was very early he was like the first rep at Cloudera, the first rep at Streamsets, then he came to dbt.

So like all in like the open source data transformation space. Now he’s at ClickHouse, right, Which is obviously like in the in the data warehousing space. So like he’s kind of built his career in this particular space. And if you’re, let’s say, I was a recruiter at ClickHouse and I saw everything before that, I’d be like, that is our person. We are going to go do everything we can to hire that person.

I don’t know about that. Think about everybody that we’ve hired at Clay. We’ve hired kind of nontraditional sellers. And actually, the thing that you can’t tell from a LinkedIn profile, but you can from things like back channels, Having a conversation with someone is like, how high slope are they? So I think about someone like, I had a rep at dbt who worked for me, spent six years at Bloomberg. We hired him in as a commercial rep, and, like almost immediately, like in the interview process, I was like, oh, this kid, this kid gets it.

Like, he’s super smart. He’s driven. He’s super coachable. Let’s go. Brought him as a commercial rep. I was like, maybe a year, a year and a half later, we moved him into the enterprise segment. Sat down with him. I was like, hey, what do you to work on together? And he was like, I’m really screwing up in the sales cycle here. Can we work on that? We like did it? And it was like, a quarter later, he he was like doing it in every single deal.

And that like just gave me the confidence to say, like, I’m gonna invest in this person. Came to me like, a year and a half later and was like, put me into this role. I mean, I can do it. And I was like, okay, let’s go do it together. And like, I think he was top three reps worldwide at dbt. So like, that’s that’s actually what I look for outside of like, you know, like domain knowledge is helpful for certain areas and certain profiles or certain levels.

So like John Dalton, who I called out, like, I’d hire John Dalton anywhere, but I’d hire him as like the first rep if I was in the data space. That’s the kind of person you need early on with like a little bit of he has a lot of expertise, but, you know, expertise, the drive to do it, that has done it before. As you get to rep 100, domain expertise becomes a little bit less important, but the high slope is the most important thing.

You know what? We actually, I incorporate this into my hiring flow for leaders. I give them feedback or I have someone else give them feedback, ideally the recruiter. And you know why? Because if I give them feedback and they push back or they’re kind of a dick about it, I’m like, oh, okay, probably not gonna work. So this is

Yeah, I’ll I’ll say, like, I’ll give an example. I hired I hired a guy in San Francisco I’m really excited about. He went on a walk with Varun. called me after, gave me a voice note and gave me gave me, like, some feedback. So I just called him and I was like, hey, how how do you think it went? Like, you know, okay, great, great, great, Hey, this is something that I got. Like, this was part of the feedback that I got. What do you think about that?

And you just listen and it tells you everything that you need to know about what it’s to be like to work with that person. If they’re like, oh, well, like, he didn’t really say it that oh, interesting. Okay. But if they’re like, okay, yeah, that’s fair. How do I go how do I go and overcome that? And they’re like, yo, what do I do That’s actually very interesting, especially in a in a company like Clay where we’re like, I don’t know, building something new. There’s a lot of like open white space.

Right? If someone’s really defensive, that’s actually the biggest red flag. And I we need to incorporate it into the into the rep interview. I I made a hire one time ever since. I’ve kind of just said, okay, I’m give you the feedback and let’s see how you react. And actually, it’s even better if the recruiter gives them the feedback. It’s sort of like when you take someone to I’ll know, take take your girlfriend, your wife to restaurant and you see how they treat, He went the hostess and the waiter.

Right? Yeah, it’s the same it’s the same thing. So if the recruiter gives them feedback and they they treat the recruiter a certain kind of way, I’m I’m out.

Ah.

That’s that’s actually that’s if you think about So like, we talked about Todd, right? Same me and Todd, we agree on that. was I like, actually don’t really care what my title is. I do care how much you pay me. I care about scope, but like, fuck, you can call me go- to- market like every other AI company. Like, I don’t really care. I actually think, I and I tell people this, If if you’re joining a sub million company and you’re the CRO, I’m like, that’s that feels my my my opinion, feels like an ego play and it feels like you are a little bit shortsighted because eventually you’re gonna stumble and then what are they gonna do?

They’re gonna say, oh, we need to hire a CRO. You’re out. Right? Now you’re not gonna learn anything because you’ve you’ve shot your shot Right?

Yeah, that’s fair.

I didn’t think about that, but that’s fair.

Versus versus if you come in as like, I don’t know, head of sales or like go to market leader, whatever, right? There’s always room to go up.

If it’s nice and actually, I listened to one of your podcasts you you’re doing with someone else, and you’re talking about this. How do you know a big enterprise rep, big deals person, how do you know? Like, they have a nine month ramp. How How the fuck are you know month three if they’re good or not? Right? You know for an IC, like, within probably three weeks. What are those signs? The signs are, can they think critically about someone else’s business? So like, and and that would be like the sign of a mishire.

You put a You put a prospect in front of them and you say, hey, here’s your target account list. You’ve gone through boot camp, the two week boot camp. Here’s your every accounts. How do you stack rank them? And they just completely whiff it. Or they’re like, I don’t know. Right? Like, oh, that’s a big red flag. The second thing is like, what are their activity metrics? Right? Like, okay, you just exited boot camp. First, I want know how they did in boot camp. Like, were they engaged?

Were they failing alone? Were they asking questions? Were they leaning on other people? Once you get out of boot camp, it’s like, okay, are you thinking critically about your prospects, their business, how we can help them? Are you fucking hitting send? Are you picking up the phone? Are you hitting send? If you’re not, you’re not generating pipeline. It means you’re not gonna be successful, right? So, like, those are the early flags of, like, this person’s not gonna work out.

Yeah, take my whole team down to Barry’s boot camp every day. Let’s go.

That’s a little bit later stage thing. When I joined Heap and when I joined dbt, we didn’t we didn’t have a bootcamp. So how should early stage founders train reps? So here’s here’s what we did at Heap. Basically, Mateen and Ravi, it’s like they showed, they did the thing, we rode along, and then that shift started to happen of like, okay, now we run the call and maybe you’re on a few. Now you have Gong, so you can actually send the people that you hired all of your Gong calls before.

Like, that’s all the founders that I work with. I tell them like, yo, do you have Gong? And if they don’t, I’m like, red flag. You gotta go just go get just buy it. And then send whoever you hire all of the calls that you’ve done. Because they’re gonna one, they’re gonna give you feedback on, like, how to sell. But two, they’ll hear how you talk about it. And that’s actually the most, that’s the most important thing to me is like, how do I take what’s in my brain and put it in your brain?

I keep coming back to like, thinking critically about your customers. So, like, I’ll give an example. Maybe you’re selling an AI widget. Does this person come in and talk about the widget, or do they talk about how, I don’t know, JPMC would use it or the company that they’re currently at, how they would use it and the impact that it has. What I mean by impact is like, I’ll give an example. Whenever we talk about AI tools, I feel like we talk about like the art of possible, like pie in the sky stuff.

And I’m like, hey, hey, hey, bring it back here, right? Why don’t you give me an AI tool that automatically tells my reps when they have a close date in the past? The basic shit, when we’re single threaded. Let’s start there. Let’s help people do the basics well before we get to like, oh, it automates the outbound and then it automates the first deck and then you know what? It automates the rest of the sales process. I’m like, okay, great, great, great, We can get there.

Let’s start with the basics. So like, when they talk about your widget in the context of their company, are they talking about pie in the sky or are they like, this is actually the real problem that it’s solving for us. And the impact of that real problem forecast is screwed up or we miss our revenue target or like our rep productivity sucks because of it. Can they tie your thing to a real business problem that they are facing and other people are facing and then tie a dollar outcome to it?

Those are the types of people that I want, and then I test for, okay, do they have the drive? Obviously, I bias towards having college athletes because they’ve they’ve learned how to work hard. All you gotta do is teach them how to work smart. If you teach them how to work smart, it’s really tough to teach someone to work hard.

Yeah, that’s true.

showed up with those pretty cool M frames.

that’s right. that’s right. The most are The pieces you post post on Instagram.

I know.

Honestly, it’s it’s really tough. And like, I obviously, I hadn’t intended to leave dbt, if I’m if I’m honest. like, I was like, I’m to finish out the fiscal year, and then maybe I’ll start to think about what’s next. And I I met Varun, and you know Varun. We went for multiple walks around. He lives around the corner from me in Brooklyn. I feel like I got a little bit of the cheat code because I I do think that Clay is like the most compelling company on the planet right now.

And like, when you think about AI companies, a lot of people have We We just hired a RevOps guy. He’s fantastic. He has this phrase. He’s like, everybody has the Claude spookies. And I’m like, that’s a really good way to describe it. The the feeling of like, well, why wouldn’t Claude just do this? Is Claude gonna overtake this market? Is Claude gonna put you out of business? Right? And it’s like, there’s a lot of companies out there that I look at it, and I’m like, I got the yeah.

I think that that could be a thing for you. And so like, the real answer is I don’t I don’t really know. But I think about, is there something that’s not just AI that’s defensible? Clay has this data marketplace. It’s really, it’s tough to build that. You could go, yeah, You could go do that. You could go buy 180 different data providers and build your own, that’s but a lot of work when you think about just buying software to do that for you. And so like I would look for some sort of other defensibility outside of just we’re automating this or like we’re we’re to automate this professional way or like a workflow.

And that’s a really tough thing to find. Like like, I can’t even think of a company that I would shout out that’s doing that. Right?

is that is 100% right.

Yeah.

It As someone who is currently selling shit that everybody wants, yeah.

It is easy in the beginning because you could grow as a company a thousand percent just by doing the thing, like, you know, having a moderate execution on your on your sales process. And And if you have a really great product, it’s to fly off the shelves. Right? But as you grow, it becomes very challenging to grow 1,000% year over year 250% year over year Right? So like, a lot of what I focused on when I was evaluating Clay was like, great that you’re landing these these logos.

How many stick around? How many double their spend with you? And like, the metrics that I got, I I think I can share. They were like, we haven’t churned a customer. Our NDR is close to 200%. Those are the types of things. if you’re talking to an AI company, that’s the biggest green flag, right? Because it’s not just can you sell the thing, it’s can you make the customer successful and successful enough that they go do more with you?

Maybe. That’s when I talk And

You’re like, it’s amazing, but it’s actually, amazing for 2011, right? people get caught up on We

Yeah, it’s impressive. It’s impressive. Here’s how I when people come to me and they’re like, should I take this offer? How How should I think about this? You know, a company, let’s call it Acme Co, right, High flying, fast growing AI startup, they might give you, let’s say they give you million dollars of stock and you’re like, holy shit, I’m rich. And And by the way, this is growing so fast, it’s to be million soon. There’s like a coefficient that I apply to that of liquidity.

How liquid is that? Do they actually do tender offers? Because I think everybody’s kind of been bit, right, by a company that’s like, oh, we’re growing so fast and we really care about employee liquidity. So we’re to do tender offers and then never does tender offer. Right? And so now you’re sitting on however much stock you have that is probably life changing for you. So like, I actually just tell people, I’m like, what have they done? Not what they say. What have they done that’s shown that they’re to provide liquidity on that on that equity and just apply a coefficient to that.

If they give you a million dollars of equity, but they haven’t done anything to allow people to you know, there’s definitely people who’ve been there longer than you. What are they doing with those folks? Just apply a certain maybe you apply 0.3x to that. Right? I’m a founder

We just rolled out a variable compensation plan at Clay. Before, everybody was just being paid a salary, whether you’re the top performer or the bottom performer. As a As a salesperson, I saw that and I said, Okay. And like, you know, there’s a lot of companies that have that have done that in the early days. Like Stripe did that in the early days.

bonus. No no cash compensation tied to any performance in a structured way.

I saw that and I said, incredible that it’s gotten you this far. Let’s figure out how you how you reward and attract and retain the right talent. Because I’ll give an example. We just hired a gtme, our version of a rep. You think of it as like a rep and a sales engineer rolled into one. We just hired a GTME out here in London, and I got off I off a red red-eye jet from JFK, got breakfast with her, and the conversation was, how do we go make a million dollars here?

How do I W to a million dollars at Clay? Walk me through the math. And that’s what the best reps want to know. I have a target. I’ll run as fast as I can towards it. Tell me how to do it. And then they’re like, If you don’t have the right math, if you’re like can’t walk walk them through it or you don’t have the right percentages, they’re like, maybe you don’t care about salespeople. But in this scenario, you’re you’re hiring what? your first first two salespeople?

Here’s what worked at Heap. And I actually really

I do, just because I’m an athlete. Right?

I think what I think what it think what it does is it just it allows people to just like, hide. And the way that I actually say this to people when they’re like, why? Oh, the variable compensation plan, what if? And I’m like, hold on here. You have a number today. You are being judged against your performance to that number. If you don’t hit that number, I’m going to fire you. And if you over perform on that number, I’m not going to pay you more. Do you think this is a good deal for you?

Most salespeople are like, yeah, if I over perform, I want to make more money. And like, know, those are the rules of the road. If I don’t have my number, you’re going to fire me. And so I understand. I think actually maybe the genesis of this is that a lot of these companies are like, they don’t know how to do comp plans or they’re like, What if, what if, what if, And so they’re like, this is actually just easier. And I think that’s maybe okay in certain areas.

But like, I’ll tell you the thing that Todd, who I just hired at Clay, we we were the first two reps at Heap and we had a compensation plan that was dead simple. It was, we had a base salary and like, I don’t know, this was like 2015 San Francisco. I think our base salary was like 60k pretty low. And then every deal that we closed We you we had to pay back our base salary. So like every month it was like, I don’t know, grand.

So the first grand of revenue was a wash. Beyond that, every dollar that we closed, we got 25%. And And if it was a two year deal, every dollar in that two year deal, we got 33%. And I have never run harder at a goal in my life than when I knew that I was going make 25% of every single deal that I closed. It aligned our incentives with the company’s incentives very, very, directly. And we just like sprinted at it. And then we compete with each other.

Be like, who could do the first deal? Oh, I got the biggest deal now. I got the biggest deal. And it was like everybody was celebrating. Everybody was making good money. And that was it. it. was simple to administer, very direct. When we built our comp plan at Clay, I feel like it’s really easy to make it really complicated Like, oh, 20% of your 20% of your variables is this, 30%. And I’m just like, just make it fucking simple. Because then it’s easy to understand and it’s easy to administer.

Everybody understands the rules of the road. And we have accelerators.

So you have a quota, obviously.

Our quota to OT ratio is like, I think it’s like seven and a half. Quite good.

Well, I think below 4x, it’s like, yikes, right? I’ve always always taught four to six. Like four is kind of shit. Six is like, wow, you’re doing great. I think in the AI era, you have 20x your base is your quota. that’s pretty wild. Punchy. Right? It’s punchy. punchy.

That’s right. It’s punchy.

Yeah. In the AI era, I feel like we’re seeing somewhere like six to 10 depending on on the business, the types of deals, size of deals, who you’re selling to. But like, we’re at and a half x quota to OT ratio today. If it doesn’t make sense, we’re gonna make it make sense. If it doesn’t make sense to have that, we’ll change quotas, or we’ll change pay, that type of stuff. We have accelerators like you would imagine, normal. So

And then you get paid more on every dollar that you close. Only then? Have you worked at a company where they have accelerators before you hit 100% your of your

Jesus fuck. So what I’m saying, what I’m hearing is you want don’t to come work for

Well, so it depends. I’m

Exhausting, Look, you have your OT and we pay pretty competitively, I would say, above and beyond your quota. And this is actually the argument that we’re actually having right now. Like I spent probably two hours in the last two days with my RevOps leader, Varun, Kareem, our finance leader, right, our strategic finance team on what are the accelerators? Because my perspective is if you’re overachieving, it should be heavily weighted towards over performance. If I’m giving you a big quota and you’re hitting 110% of that, I want you to be making good money.

If you’re hitting 150 of that, come we come back to what’s the percentage of quota attainment to make a million dollars? That’s the number that we’re fighting over because if you have, let’s say you have reps, 100 reps, Right? 60% of them are hitting their number. Great. Just Just hitting. They’re making their OTE.

The culture that I think is best is when you have 60% of people over 100%, 80% over 80%. You’re building a winning culture. People are successful. People are telling their friends they’re having so much fun. Very successful. Come work here. You get the best talent. That’s like a a rule of thumb that like. I like. Our strategic finance guy was like, oh, it’s 50 over at 100 at my last great. Whatever. You agree on some percentage of your team is over a 100% and a certain percentage is over 80%.

And if those things are true, it builds the right culture, which is actually really important in sales.

And usually you can tell by the reaction. Actually, coming back to Heap, they hired both Todd and I at roughly the same time. I think Todd was like three, maybe three, four months before me. And they told us like a year later, were like, we hired you two at a time. I tell every founder this. I’m like, hire two at a time because then you’ll actually see you hire one, you’re like, is it good? Is it not good? I don’t know. If you hire two, it’s pretty clear whether one’s good and one’s bad.

They told us like a year later, they were like, yeah, we hired both of you and we’re like, We’ll probably have to fire one and keep the better one, but you both were really good. So we kept you both, and I was like, oh, okay. Well, thanks. But like, that’s how you do it, right? let’s say you have 100 reps. There’s gonna be five that just bitch about quota and blah, blah, blah, But if you dig under the covers, they’re probably not doing the work to go and be successful, right?

And those are the people that you probably don’t want on the team.

Sounds fancy.

every pipe. That’s coming to our sales floor. We’ve hired nontraditional salespeople, so you kind of have to incrementally introduce some of these concepts. like, you better believe we’re to build the sales dashboard of how much revenue have you closed? How much pipeline have you generated? What’s been your activity this week? Who’s at the top? Probably the person who’s at the top bottoms up is going be at the top on the revenue dashboard.

That’s why if you create like a zero sum game, everybody’s kind of just looking out for themselves and they’re very scared versus that’s why I was like 60% over 100%, 80 over 80, creates this culture where people are excited to help each other and they’re excited to celebrate everybody else’s success. You think back to me and Todd, to be fair to like, for the record, I closed the first six-figure figure deal at Heap, and then he was like, awesome. Fuck. I want go do that too.

Okay, I’m to go get a bigger one. Go get a bigger one. Go get bigger one, right? And And we’d be bouncing ideas off of each other the whole time. It’s like we wanted to help each other because we knew that we were building this thing together, but we were like, I I want go beat you. And I think even even at dbt, right, which is like open source product, open source company, very like open source minded. So like, it’s like a different approach. You’re giving away software for free, and then you’re also trying to charge for it, which is kind of weird dance to do.

Once you get big enough, you do you do teams, right? So like, the last year that I was there, the central team closed the biggest deal in history. And then the EMEA team’s like, well, fuck, we we need to go get, you know, Siemens or Allianz. We need to we need to go get a bigger deal there. And you kind just cut you pit people against each other in a in a fun way or like, you know, me and Alistair. So Alistair ran EMEA for me at dbt, and he would always say, here’s the percentage of the company’s revenue that comes from EMEA.

And you’re like fighting over market share. And then I would go to the I go to the America’s team. I’d say, hey, make sure that make sure that he doesn’t get any more points, right? Hey, your goal is actually that he goes from 34% to 33%. Right? And you just of like you put a little chip on people’s shoulder, but in a fun way.

It’s not demoralizing if the company’s growing if the is growing 3 to 4x, which just you just me inherently You’re becoming

Sounds Sounds like you have some reservations.

So like if I pay you 10¢ on the dollar before, it should jump pretty But for every

It doesn’t jump up that high. You know what? know very disappointing. Why

I mean, we did it at Heap because we were the first two reps and they were like, fucking close as

I think it depends on the economics of your business. So if you think about Clay, we pay for the data that we sell, So we pay per credit in the same way that like, we charge for a credit of data. And actually our economics are very, very, good. Our head of finance is really smart about all that type of stuff. But in some businesses, you have shit margins. And I’ve worked for companies that have less than ideal margins, and and it kind of compresses what you can actually pay.

So maybe that’s something that you look for in the AI era is good margins. I don’t actually know why we can’t do that. There’s some sort of flat pay that you have a base commission rate, then on top of that you get accelerators. All that Heap did was just jump straight to the accelerators and say you have an artificially low base. Now go now go work your ass off.

I think if you You’re talking about like a PLG motion, right? And if you have usage, your your job then becomes, what are the next use cases? What are the next teams? You’re fighting over, like workloads, right? Rather than going and landing a logo. Because if you think about, think about, Salesforce, how many places, how many entrances are there for different AI tools? And then how much market share internally at Salesforce do they have? So like if you go land a logo, let’s say Salesforce is on is on a PLG motion for your company or AI widget, and that, you know, you got, like, three people in the marketing team using it, three people in the sales team, whatever.

Right? Your job then as the rep becomes how do I go take that market share in that company faster than any other AI company or any of our competitors can come in and take some of that. Because once they’re in, then you’re fighting with them over workloads versus fighting with inertia. So it’s almost like, can you go into an account and suck the oxygen out? And that’s actually how I think PLG businesses do really, really, well. Someone comes in, they’re dabbling in the product, Right?

And you as a seller, you’re like, I’m to go market that internally at that account to all of the other people and pick up all of the other use cases and secure the borders of that, not to be too American, but secure the borders on that account from anybody else. It’s like risk.

proud. but, proud. you But about you think about going and securing securing your land in that account so that other competitors can’t come in. I saw this with Snowflake and Databricks. right? Snowflake would own everything, and then Databricks would get one small foothold somewhere. and suddenly now they’re fighting over the same workloads and someone’s to win that.

Okay, so if you actually ask anybody on my team, I hope that they don’t listen to this because they’re to groan. I will oftentimes just say, okay, do do you have a champion? And they’re like, I have a I have a yeah. Yeah. Yeah. person’s my champion. I’m like, what are the three characteristics of a champion? All of them know. It’s they’re selling for you when you’re not in the room. They have access and influence over the EB and they have a personal win. If you focus on those three things, if you focus on honestly just the personal win, like, yo, why are you

Yeah. So like I’ll give an example of a champion of Clay at a company that we all would know. Her win is she’s like, hey, I’m becoming the AI person. I teach this AI course at the university in this large city, and I’m talking about how I’m using Clay and I’m building my personal brand. And like, I of to get into like venture and investing and advising companies on AI and like, I’m leveraging what I’m doing with Clay to show that I’m that person. And I’m like, that’s an that’s an incredible personal win.

At dbt, like, you would talk to folks and you’d be like, yo, why why you care so much about this? this? is just data transformation. They’d be like, but I to be the data guy. I to be the guy that owns the entire data and does all this cool shit. And then when I leave this company, I can go to another company and be the data guy and come in, you know, higher salary, get more equity, whatever. If you focus on that, if you if you if you can get to that, you probably have a champion, and they’re probably to go to war for you, and and and they have to have the other two things.

Well, I’d start with why. Why it slip? Honestly, they took longer to get back to me than I thought, and we just didn’t get over Here’s Here’s a big one. Oh, this actually happened to to one of my reps. Oh, you know, didn’t know how many approvers needed to sign this big expansion. The signer is actually the CEO of this big company. He’s on his island in Hawaii. Fuck. And I’m like, okay, well, like, let’s let’s break this down. Is there someone internally that could have told us that?

Yes, Probably. Right? So then did we talk to that person? It’s like, did you talk to that person? Did you ask the right question? Because those are two different things, You might be talking to the right person, but you just didn’t think to ask the question and they didn’t think to tell you because their job is not to buy software. Sometimes it is for your procurement. Right? And then I go to, okay, well, who’s your champion? Do you have a champion? And oftentimes what I’ll hear is someone mistaking a coach for a champion or a person who’s dabbling in the software as a champion.

They assume it’s the champion versus I always use this when I say like, and what have you seen with your two eyes that tells you that this person’s a champion, that they have those three attributes. What have you seen with your two eyes? And people make fun of me, but they remember, right? And now they’ve gotten better at it. So, like, we just opened a London office. I was talking to to one of the GTMEs out here she was like, oh, well, yeah, yeah, he’s a bad champion.

I’m like, whoa. Woah. hold on here. And you kind have to be meticulous and, like, kind of an asshole about when people say, like, qualify champion. And, like, no, no, no, It’s it’s binary, right? Like, if you’re a bad champion, is it you’re really your champion? Right? You’re either a champion or you’re not a champion. Like, let’s be really clear about it. And if you’re if you say they’re a champion, what have you seen with your two eyes? Tells you that they’re selling for you when you’re not in the room.

They have access and influence over the EB, and there’s a personal win. It’s It’s pretty simple. If you don’t have a champion, you’re probably not to get a deal done. Or if you get a deal done and you’re like, I didn’t have a champion. You had a champion. You just didn’t know that they were your champion, and you probably didn’t do the best job.

Every week on Thursdays, every one of my frontline managers goes and does a forecast call with their team. And they either do it as a team they do it individually. I actually don’t care how it gets done, but I do care that you’re sitting down with your rep and saying, okay, walk me through what’s the pain we’re solving? And then it’s like, what metric is attached to that pain? And then who gives a shit about that metric? Are we talking to them? Right? Like these types of questions that help us understand, do you have control of the deal?

Is the deal in the right stage? Right? Are we Are we making assumptions? Do we need to go back and actually you get to the end and something happens and you’re like, I have a bad champion. Well, actually, you’re back here and you skipped a couple steps, right? Let’s just be real and move it back there now and go do the work to actually build the right deal. So we do that once a week. I do that with my frontline leaders on Fridays. And the way that I do it is I just model the behavior that I want them to be doing in their forecast calls.

And I expect that they’re in the deals in the same way that like, I’m running a couple deals with reps, and it’s a lot of fun.

At the frontline, not being in the details, not being in the deals with the rep. I’ll give an example. I talked about John Dalton earlier. John Dalton is like one of my favorite people. I I would love to work with John Dalton for the rest of my life. He also lives in Santa Barbara. very chill. He has a very, very, nice life. John Dalton, if you asked him, hey, what’s going on with company? He knows because he’s in the deal with the rep doing the work, showing the rep, here’s how you do a good deal.

Let me teach you how to run these types of deals. He’s in the deal, so he doesn’t need to look at his notes. He’s like, yeah, this happened. This is the immediate next step that we’re doing to get to the EB or to, you know, we have a call on Friday to talk about all the approval processes and the signing process versus, you know, you might ask Stacy, hey, what’s going on with And she’s like, let me check let me check my notes. Ah, the last update.

And I’m like, I can read the update in Salesforce. We have a specific, like standardized way of writing your next steps. I can go read that too. But what what is your perspective on the deal? Are you in the deal? And like not every frontline manager can be in every single deal. So you have to choose which ones are the most important. Right? And it’s usually a factor of like how tenured is the rep? how good is the rep? What are we trying to develop with them?

Is it a high profile deal? Is it a great logo that we know we can go and expand? Is it the biggest deal? Right? Like, however you decide, you decide, But that’s probably the biggest mistake that I see for frontline leaders.

is going because they’re competing for the same workflow in your account because you didn’t secure the account. And you’ve got cushy

I mean, look, you’re kind of getting into the question of like, what’s the model of the go to market team? Right? And like, I’ve been in models where you do a full handoff. I’ve been in models where you do a handoff, you keep it for months, whatever. My favorite model is you sell the deal, you’re renewing the deal, you’re comped on net dollars. So what that does is that incentivizes the rep to sell a good deal, right, and protect your unit economics. Someone on John’s team sold a deal that was slightly above list price, right?

Wow. They had a much easier time than the rep that discounted 40% and is trying to go and claw that back now. So it it helps protect the unit economics because you know that you’re to have, you to go and expand that. But two, you sell a shitty deal, you’re to renew that shitty deal and you’re probably going take some churn or contraction, right? And like that’s actually the model that I love because it incentivizes you, the hunter, to go and secure the border in that account.

Right? And not let anybody else come take your workflows. You look at like a Snowflake or a Databricks, that’s their model and and it’s because they’re competing over workflows in the account. It’s the same for us.

think that’s a shitty way to incentivize people. Here’s why. Someone said this when I was at dbt. This was a long time ago. We were talking to a buyer and they just straight up called us on it. They were like, is my money not green on April 1st? And I was like, Fair play. right? think everybody knows at this point that if I’m giving you a discount on the last day of the quarter, you’re probably going to be able to get that same discount on the first day of the next quarter.

And when we buy software, I don’t know, the rep was like, hey, I can only do this if you do this by next Friday. it’s like, actually, I don’t give a shit about your timeline. I need this software today. So yeah, I’m to move fast. We know, We bought a forecasting tool. I need this because I have no control over the business. I have no visibility into what’s happening. I need this more than you need to sell this deal. So sure, I’ll take your discount, but we’re dollars try to get this deal done before next Friday.

And So if you find that, that’s why I’m like, what’s the metric that we’re attached to? Who cares about that metric? Now go talk to that person and say, hey, how do I help get this in your hands faster? And if they say, I don’t really care about it, you probably, you probably skipped a step. Let’s go back and let’s figure it out.

Absolutely not. No way. So it’s funny people ask this question. When I first started Clay, they were like, SDRs, what’s your perspective? And I was like, I’m building an SDR team. I’m building a ClayDR team because outbound will never be dead. You can’t reach every single company and every single buyer with whatever marketing you’re doing. Or if you do, it’s less efficient. Right? It might be efficient when you’re trying to generate million of pipeline because you have a, I don’t know, 10 or million revenue target.

But like when you get into having to build a quarter billion dollars of pipeline, like, it’s actually probably a little bit more efficient to just put some hungry, scrappy 24 year old on the field, pay them, you know, a certain amount of money and say, go run at these accounts. Right? That’s the first thing. The second thing is like, hey, you you don’t have an SDR team. Who the hell are you to promote into your closing roles? It’s competitively, de risked if you have an SDR that you’re promoting.

Those are the best people.

outbound is not

No, Outbound is not

Everybody should be responsible for pipeline generation. Everybody owns pipeline. I’m out here. We We have, we call it Clay Day on Tuesdays. You might know it as its former name, PG Tuesday. Yeah. Every Tuesday, I ask my team, hey. who can I reach out to for you? you? know, we have a whole channel called multithreading requests. Who can Varun? Who can Kareem? Who can our chief of staff, Julia? Who can she have our VCs reach out to for you, rep? Because everybody should own pipeline generation to help make the rep successful.

That’s it. It’s so funny that like, just the same message coming from a different mouth

Yeah. It It gets a completely different response. And so, like, I encourage people to think about it. One of the GTMEs that I was talking to out here in London, you know, Tuesday rolls around, we kick off Clay Day. I’m like, hey, what’s working well? She’s like, you know what? I’m just doing the basics. I take an account and I think about what are all of the ways that I can go and make contact with them. So is it a VC? Is it me? Is it you?

Is it our partners? Right?

Yes. 100%. 100%.

Yeah.

I I tell people I need to be better at this. I need to follow my own advice. We do really cool shit at Clay. So I’ll give an example. You can if you work at Clay and you to try out a new AI tool, you can just go into a channel and say, can I have a ramp card to try this tool out? And they’ll give you a ramp card. Like, no questions asked. They’re like, I want to try this AI widget. Can I do it?

And they’re like, yeah. get after it. Versus like a lot of other companies are like, oh, that needs to go through approvals. needs to go through our AI council and they need to evaluate it and we’ll get back to you never. How’s that, right? And so things like that, I’m like, whoa, hey, you should actually post about that because, one, that’s something that no other company is doing. And anybody who’s out there and sees that and is currently rotting at their company, they’re like, holy shit, I want to do that.

We do a lot of We talked a lot about the cultural things that we do that are that are fun. I think that it should have some sort of learning or training. Hey, I’m getting better at my job. I think that’s a great way. that’s modern marketing. You said

I didn’t say it doesn’t change it. I just said it doesn’t replace it. I think about this, like, if I can, and and this is like my thesis with the ClayDR team is like, let’s say 2018, an SDR can book in a in a given month. Say they’re booking 15 meetings, right? right? If I can arm that rep with Clay and a a Claude seat, maybe a lovable seat, I don’t know, I can tool them with some sort of AI stack And now they can book 40 meetings a month.

I’m to say, yes, please. Thank you. Okay? Now I want grow my team of SDRs from eight to fucking infinity, right? Because I see a ton more productivity. Anybody that’s like, oh, well, you know, we’re just gonna cut our SDR team in half. I’m like, okay. that’s an interesting move, right? That’s a That’s a scared play that you’re making because you’re saying I can get the same productivity for half versus saying can get this productivity, and now I’m gonna go multiply that into infinity and take all the space, all the oxygen out of these accounts.

Well, I think how many businesses do you think out there can actually replace the entire SDR process and just hand it off to an AI Right now, none. Right? Yeah. So it’s like, okay, you’re going have some number of SDRs. What’s been the best AI

I don’t know that I have particularly found the AI tool and brought it in, but here’s like two tools that we use pretty aggressively. Like everybody uses Level, everybody uses Claude, right? I was talking last night with a of my team about on the plane back to New York, I’m probably just going to look at the Claude saved projects and just steal a bunch of ideas. The two tools that I’m obsessed with right now, Granola. Everybody’s obsessed with Granola. Great. They just raised a big round.

Happy for them. The other tool is Whisperflow. Are you familiar with them?

money. Well, Chris

Well, they gotta think what,

know what, though? It’s very objective. I did a reference call last night on my phone, and I used Granola to take the notes, and I just sent it to Varun and my partner. And it’s very cut and dry. There’s no emotion in the granola notes. And Varun was like, is this a positive? Was this a positive reference? And I was like, yes, it was glowing. And I looked back at the granola notes and it was just objective. Like, yes, Stacy helped me in this deal. Like, blah And I was like, okay, got it.

I’ll figure out a different process. So they got some things to work on.

Yeah, that is kind of annoying, especially if you don’t have it open. So hey, Whisperflow, if you could fix that for me, that would be really great. So annoying. But I love that, I’m with you. I don’t know if you have this problem. If I open up a new email tab and I just have a blank email, I get I’m like, oh my God, Like, what am I gonna say? If I can just press a button and say, like, that’s how I I send out like, a weekly update.

And if I can just press a button, I say, yo, squad, this is what’s going on this week. Here’s the numbers. Here’s the pipeline. Like, da, And it does the whole thing for me. And I just hyperlink And you can

yeah. So I don’t know if you know Bill Binch over at Battery.

Oh, yeah. I I have a ton of respect for him. if if you’ve been an operator that long, God, you’ve got some thick skin. But he said the other day, he was like, no one’s to type anymore. If you’re typing, you’re behind. You should be talking to your technology. And I was like, that’s a weird way to think about it. It’s like a very futuristic Jetsons way to think about it. But it’s actually true. I don’t really type that much anymore.

I mean, we use Clay. right? We use Clay to supercharge our SDR team. Because if I can build a system that then tells the SDR where to focus, and then I can go train that SDR, let’s a dick.

not that intuitive.

Well, it’s not that easy.

Okay.

Well, so actually, it’s It’s bit of a

problem. That’s right. It’s the same problem as WhisperFlow and email, right? It’s a spreadsheet. You open it up. It’s a blank spreadsheet. So where do you start?

You can now. Well, can’t verbal. You can type diarrhea. Maybe if you can use WhisperFlow into Sculptor, is like our of like, you know, clippy from the Microsoft Word. Right? Sculptor is like our little Clippy, you can say. I’m trying to find the 100 best Indian restaurants in London and find out who their owners are, what is their Yelp reviews, and what are people actually saying in those Yelp reviews is the best dish And then craft me an outbound email saying, hey, owner, I’d love to sit with you on Thursday and talk about whatever while we eat this dish.

You can put that into Sculptor and it will build the table for you. So you’re actually not starting because that that was like when, you know, when I was, interviewing or talking to Varun about joining Clay, there were a bunch of things that I was like, hey, and what about this? Because my wife uses Clay. Or like, we bought Clay at dbt. Like, what about this? this? is a gap. And I’d be like, yo, this blank it is a blank page problem. How do you start that?

And he was like, we’re actually building Dick Coleman, Is that

claudified? You could probably use Claude to say, hey, give me the top 50 oil companies in Austin. right?

Well, I think Well,

But But think about it. One rep could do that. How do you do that when you have a 100 reps? What do you do How do? you scale that out? How do you add in something new and iterate on it? That’s a lot of people we talked about my favorite phrase, the Claude spookies, right? Like, oh, why doesn’t Claude just do that? It’s like, hey, have you ever tried to like, get a 100 people to do something different, to change something to iterate in the same way that you iterate?

Good luck. Because we’re still humans, right? We’re not bots yet.

Yeah. we’ll do we’ll do our best.

Focusing on the last company that they were at and if it was a playbook company or not. like, I’ll give an example. It’s actually interesting. You see, I don’t know if you saw, Brian McCarthy just joined Cursor from Rubrik. And actually, you know, I was texting with a friend last night. A lot of people are now moving from Rubrik to Cursor. Rubrik, very Playbook company. Cursor AI first company. And I have a ton of respect for those guys and all Playbook folks. And like I think what they’ve done and what they’ve taught the craft of sales is really, really, valuable.

It’s if be very interesting to see how they modify their playbook to be AI first, because I think there’s a lot of parts that are still very relevant, but I think there’s some parts that are to be thrown out. give an example like understanding entire business case before you do anything in the product or you show any value. Like, you can’t really sell that way in the AI space. So like, I’m very interested to see how that works. But like, I’ve worked for leaders in the past that they have a certain hiring profile and they do not want to deviate from that even for high slope individuals.

I think that that’s a mistake because then you just get the same you get a 100 of the same kind of person versus people who are to actually push the envelope.

12 months ago, I actively resisted using AI. I was like, I think it’s to make people dumber. I think that, you know, you see some folks that just ask Claude the answer rather than reasoning about it themselves. And I was like, oh, I don’t love that. Obviously, like, now I work at an AI company, so maybe maybe I’m a hypocrite. But basically I went from saying, fuck that. I’m not to use this thing. I’ve got a brain and I’m to use it. To, okay, how can I offload some of the things? or how can I teach Claude to think like me so that I have two of me and I can converse with myself and be my own thought partner?

person? In person with customers or in person in an office?

I’m a five day five-day-a-weeker. weeker. I show up to the office five days a week. I’m here in London for these four days. Tomorrow, I’m gonna go to the office on Friday. I think that you get so much more when you’re working in person with your team. Like, I get FOMO when I’m not in the office.

It’s three weekend. Look, I don’t track track attendance. And like if you’re a if you’re productive, you work from wherever. You get a little bit of flexibility. But if you’re underperforming and you’re not in the office, we’re gonna have a conversation. What would

like to

about the world of sales? I think everybody would say this. I think people feel like they don’t want to be sellers. So like, maybe you’re a product leader and you’re like, I don’t really want to go into sales because it feels a certain way. I think that if people understood that, like, hey, we’re not just making 150 cold calls a day and indiscriminately trying to sling our product, like, no, I actually thought critically about your business and here’s how I can help you. I wish people would view sales more like that, but I understand there’s lot a of us out here.

That’s a good question.

you.

Yeah, You finally got a good one. I’ll tell you how we’re thinking about it at Clay. We’re going to spin out a small new verticals team. And the reason that we’re doing it is because we don’t have a complete understanding of the data coverage or the data sources. Do we have them? Do we have the right coverage? We don’t have a motion of where we land. What’s the story that we tell? So I think when you’re trying to enter a new vertical in a concerted way, that’s when it makes sense.

I also think when there’s some sort of like expertise that you need, so like everybody has a finance vertical or they hire someone in Detroit to sell to the big auto companies, If there’s some sort of like differentiated expertise, I think that makes sense. Here’s where it doesn’t make sense is where, yeah, I’ve got my guy at JPMC and he just buys whatever. Like that’s dead. Like the relationship type of sale of like, well, I know all these people, I have this Rolodex, that’s gone. Because I think today the buying cycle, the buying committee is not just one person.

You have to have the product that can go and satisfy the needs of multiple people and multiple kind of divisions in a business.

I’m not a math major, right? So there’s a math equation in there that I don’t know the intricacies of. I’ll tell you the ACVs that I’m less excited about as a sales leader. Anything below 20K, I’m like, why do you have a rep? And if it’s not like a very short sales cycle, like I’ll talk to some founders like, average deal size is 25k and our deal length is six months. And I’m like, what are we doing here, guys? Right? If you’re spending that, you’re either spending way too much time with these folks or you could add at least another zero and justify it.

Right? You You talk to like HubSpot and they’re at the size where like, yeah, they’ve got reps that are working like $9,000 deals. Right? They’re at a different scale. And they

Yeah, Right? And they’re like, our average, you know, we we do a three call close and it’s $9,000 MRR, and, like we’re just focused on logo acquisition because we know that we can go double those. Okay, cool. That makes sense from a business perspective.

That’s a good question. Thank

What What time What time frame? Any. I worked on a deal with a rep at my last company. It’s a large bank in Australia. It’s one of the big four banks. And one, we had a we had an EB. She was the chief digital officer, chief data officer, and she just fucking got it, man. Like, she she was maybe a little bit earlier in in career for for like, a a c level role. She was super innovative. She would come to us and she’d like, yo, I’m checking out these other tools.

What do you guys think? How do they play? Like, does this story make sense? So like, it was almost like working with a friend that was like really smart that was putting together their data stack. The use case was the coolest though, which is they were using our product to basically create new derivatives that they were to sell to my my classification, poor rich people, people who had between million and million of net worth. And they were to launch 10 of these products and they were expecting each of those products to generate million for them.

And I was like, wow. Like, you’ve thought about, like, we we kind of uncovered all that and helped them build the business case, but, like it was something that was like a very intricate use case that had a huge financial impact. And it was just, a it was a fun team. I actually, my favorite deals are not the biggest deals. It’s the deals where like I’m working on one right now with one of the gtmes on my team. And like, I show up to the calls and, you know, we have our plan.

We know what we’re trying to do. We’re like, hey, we need, you know, we need to drive these steps. But like, the people on the other end of the phone are two women who like have their shit together very clearly. And they’re like, we need to make a big change in this company. And like, here’s how we’re thinking about doing it. You guys have done this with other people. Are we thinking about this the right way? And I’m like, you’re thinking about it exactly the right way, Christy.

Like, you’re doing great.

Me personally? Yeah. It was million for three years. So it was, you know, like 3.3 TCV with a large financial services company.

It’s It’s a good day.

The best advice to new parent, actually, my wife and I talk about this all the time. If you have a rigid schedule, then the kid can be off schedule. If you don’t have a rigid schedule, you’re like, the baby eats when the baby eats, the baby sleeps when the baby sleeps. No way to get off schedule. No way to feel down about yourself, feel down about the kid. You just go with the flow. Makes your life a little easier.

Yeah, there’s a little bit of that in there.

Thank you for having me. Really enjoyed it.