Inside Clay's Sales Playbook | Becca Lindquist

How do you read a LinkedIn profile?

Oh, wow.

Which 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.

Today, we have Backer Lindquist, head of sales at Clay, one of the fastest growing companies to scale to $100 million in ARR.

Our quota OT ratio is like 7 and 1/2. It should be heavily weighted towards overperformance. If I'm giving you a big quota and you're hitting 110% of that, I want you to be making good money.

This was an exceptional deep dive that goes very granular into how to scale a sales org.

When you have 60% of people over 100%, 80% over 80%, I think is best. You're building a winning culture, people are successful.

Get your pen and paper out. You'll be taking a lot of notes in this one.

Hire 2 at a time because you hire 1, you're like, "Is it good? Is it not good? I don't know." If you hire 2, it's pretty clear. Outbound will never be dead. Ready to go?

Becca, it is so good to have you on this show. It's so nice to do it in person. I went for a walk around Hyde Park with Varun, and he said so many wonderful things, so thank you so much for joining me today.

Thanks for having me. It's fun.

A lot of sales leaders and salespeople are looking at themselves and saying, “Am I in the right place?” You're in a SaaS company, and you're thinking, “Well, it's not an AI company.” You're seeing a lot of friends make a lot of money at AI companies. How should people actually think about the decision: should I leave my SaaS company and join a hot AI company, or should I just stay?

I have a lot of these kinds of conversations, both with peers and with folks who are evaluating this, and I think there are 2 ways to approach it. A lot of folks I talk to are at software companies. They've been there for 4 or 5 years, and the learning curve has kind of flattened out.

The phrase that I use to describe how they might feel is, “Hey, do you feel like you're rotting?” You're not learning a ton more. The learning curve is flattened for you. You're not in an AI space, which I think is 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 fix that then,” because once you stop learning, as a person, I think you start to settle, and then it's just a process of settling all the way down to the bottom.

What do you do when you feel, as a sales rep or leader, that you are rotting? What do you do?

You have to go find something else, right? You can't reinvigorate it. Maybe you can move into a different role or a different subsector of the company, but usually, if you've been there for 4 or 5 years, the company is pretty big. There's a lot of structure and process. There's not much more for you to innovate meaningfully.

Maybe you could go run the company's VC fund or something, This is partially why I joined Clay, right? If you leave a company like that and move to a next-generation AI startup, you're going to learn way more. The surface area of what you can actually go and impact is much, much higher. I think that's what those types of people are excited about.

If you've been at Salesforce for 12, 13, or 14 years, you've probably had an incredible run. You probably really enjoyed that, and you're probably going to stay there. But most people are at companies for 4 or 5 years.

Dick Coleman, if you've been at Salesforce for 12, 13, or 14 years, I automatically think you're not great. I'm like, “You got stuck in your ways. You've been there for way too long.” Seriously, you were happy just in this melee of mediocrity for 12, 13, or 14 years. Is that a bad read?

I don't think it's a bad read. 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 recruiting last week or the week before. One of the things that we talked about is, “How do you read a LinkedIn profile?”

Oh, wow.

Right? We just pulled up people's LinkedIn profiles. We pulled up yours. It was actually really weird. We were like, “Don't hire this guy.” No, I'm kidding.

It's terrible. Look at that page: egotistical, arrogant. Why would I hire him? He's a diva. Next.

So, we pull up a LinkedIn profile, 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?” There's a certain amount of time that, if you spend it at any company, is 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?”

What is that amount of time? Because I also hate the job-hopping. I don't know—the biggest red flag for me is 13 months here.

Yeah, there's a lower bound, too, and I think it's 2 years. I would say 4 to 5 years is optimal.

Yeah.

I've spent the last decade at 2 companies. I've built something, I've learned a ton, and when that learning curve starts to cap off, you start to think about what's next and what's new. I think it's probably 7 years—6 to 7 years. After that, if you've been in a company for 8, 9, or 10 years, the company is probably kind of built around you, and you've built so much of it, too.

I don't know the best way to describe it. It's like putting on someone else's shoes, right? Now you're giving me your shoes, and I have to redo the laces. The insole's all screwed up. I think it's really tough for someone who's been in a company that long to adjust. Prove me wrong, right?

I have a friend who was at Heap, which I was at 2 companies ago. He was there for 8 or 9 years, and every time there was a LinkedIn anniversary, it was like, “Your friend has been there for this many years.” One year, I just screenshotted it and sent it to him. I was like, “Yo, blink twice if you need me to save you.”

He was like, “Look, I'm learning, and yes, there is an end date. There is an expiration date.” But when I see something like that, especially at a company like Salesforce, I'm like, “Okay, you have your thing. You know what you're doing. You probably have great hobbies outside of work.”

Don't put that on me. That's so derogatory. I love that. That's so funny.

Training recruiting—take me to that day on LinkedIn specifically. Is there anything else you watch out for? Don't laugh, but one of my big red flags is someone who has a picture of themselves speaking at an event. It just tells me that they have great self-importance. You're just a dick.

Well, actually, when I see that, I look at it and I'm like, “Okay, either you're at a conference, or the vast majority of them are you speaking at a wedding.” And you can tell.

Oh, wow. That's bleak. That's really sad.

And then, look, I don't have the perfect LinkedIn profile. I should probably invest way more in it. Everybody at Clay is like a social media star. I'm actually very averse to that because I'm always terrified of saying something really stupid. You look at my LinkedIn and it's—

You're lucky you're on a podcast.

Yeah, great job here, right? But I look at my LinkedIn and 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 a lazy eye in my picture, and it really bothers me every time I look at it. When I look at other people's LinkedIn profiles, I'm like, “God, what do they think about mine?”

When I look at a LinkedIn profile, what's a red flag? Obviously, jumping around. Here are some of the other tips: you discount recommendations, right? I don't give a fuck about how many recommendations I have, but some people do.

Yep.

I just discount that, right? Any big green flags? For me, data centricity is really helpful. If you talk about your Heap experience—

Of course.

—and you're like, “I drove a 387% increase in SDR volume,” whatever it is, or pipeline, that's helpful. People love to put, “Oh, is it President's Club?” or “Here's what I did on quota,” right? That's a green flag.

When I look at someone's LinkedIn and I can't tell the story for them, I'll give an example. All of the companies are great—I love them—but imagine you're looking at someone's profile and they're like, “Yep, I did 2 years at Snowflake, then I did 4 years at Lattice, and then I did 3 years at Marketo.” You look at that and you're like, “This is kind of a mishmash of companies. What's the story? Where's the expertise that you're building?”

Can you explain that to me? Do you want aligned companies where you see aligned knowledge growing in that sector?

A little bit.

Think about a guy who worked for me. I actually think I gave you his contact info. His name is John Dalton.

Yeah.

We worked together. We built dbt—I mean, gosh—for 4½ years together. If you look at his LinkedIn from the outside, you can see a very clear story: “I’m becoming the early-stage data sales expert.” He was very early—he was the first rep at Cloudera, the first rep at StreamSets. Then he went and did something else like that in sales, and then he came to dbt. It was all in the open-source data transformation space.

Now he’s at ClickHouse, which is obviously in the cloud and data warehousing space. He’s built his career in this particular space. If I were a recruiter at ClickHouse and I saw everything before that, I’d be like, “That is our person. We are going to do everything we can to hire that person.”

That’s so interesting you say that. I’m really like that, but I have so many sales leaders on the show who say, “I don’t care if you don’t have the domain knowledge. We can teach that, but it’s much harder to teach knowledge of contract size. I’d rather have someone who’s dealt with large enterprise before than someone who’s worked in databases before.”

I don’t know about that. Think about everybody that we’ve hired at Clay. We’ve hired nontraditional sellers. The thing that you can’t tell from a LinkedIn profile, but you can tell from backchannels and from having a conversation with someone, is how high-slope they are.

I think about someone who worked for me at dbt. He spent 6 years at Bloomberg, and we hired him as a commercial rep. I can’t remember if it was 6 years, but he came from Bloomberg. Almost immediately, during the interview process, I was like, “This kid gets it. He’s super smart, driven, and coachable. Let’s go.” We brought him in as a commercial rep.

Maybe a year or a year and a half later, we moved him into the enterprise segment. I sat down with him and said, “Hey, what do you want to work on together?” He said, “I’m really screwing up in the sales cycle here. Can we work on that?” We did, and a quarter later, he was doing it in every single deal. That gave me the confidence to say, “I’m going to invest in this person.”

A year and a half later, he came to me and said, “Put me into this role. I could do it.” I said, “Okay, let’s go do it together.” I think he was a top-3 rep worldwide at dbt. That’s what I look for outside of domain knowledge, which is helpful for certain areas, profiles, or levels.

John Dalton, who I called out, I would hire anywhere. But I’d hire him as the first rep if I were in the data space. That’s the kind of person you need early on: someone with a little bit of expertise, the drive to do it, and who has done it before. As you get to rep 100, domain expertise becomes a little less important, but being high-slope is the most important thing.

When you’ve made a bad hire, what did you not see that you should have seen?

You know what? I actually 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, “Ooh, okay. Probably not going to work.” So that’s—

In the job interview?

Yeah. I’ll give you an example. I hired a guy in San Francisco who I’m really excited about. He went on a walk with Varun, and Varun called me afterward, left me a voice note, and gave me some feedback.

So I called him and said, “Hey, how do you think it went?” He said, “Okay, great, great, great.” I said, “This is something I got as part of the feedback. What do you think about that?” You just listen, and it tells you everything you need to know about what it’s going to be like to work with that person.

If they say, “Oh, well, he didn’t really say it that way. Oh, interesting. Okay.” But if they say, “Okay, yeah, that’s fair. How do I go and overcome that?” or, “What do I do?” that’s very interesting, especially in a company like Clay, where we’re building something new. There’s a lot of open white space.

If someone’s really defensive, that’s actually the biggest red flag. We need to incorporate it into the rep interview. I made a hire one time, and ever since, I’ve just said, “Okay, I’m going to give you the feedback, and let’s see how you react.” It’s even better if the recruiter gives them the feedback.

It’s like when you take your girlfriend or your wife to a restaurant and see how they treat the hostess and the waiter.

One of the biggest signs I look for is how they treat the bar and the staff.

Right, yeah. It’s the same thing. If the recruiter gives them feedback and they treat the recruiter a certain way, I’m out.

Stuff like that just beats me. The one thing I’ve learned about hiring is that when they push on title, that’s bad. When they push on salary, they tend to be good and know their worth.

All my bad hires are when someone says, “I’m not happy being an EA. I want to be a chief of staff.” I think, “Ah, you’re an EA. You’re happy with the salary,” but that’s actually always a mistake. When they say, “I don’t care about title, but I’m worth more,” that’s when I make mistakes.

That’s actually—if you think about it, we talked about Todd, right? Me and Todd agree on that. I don’t really care what my title is. I do care how much you pay me, how much equity I have, and what my scope is. You can call me go-to-market, like every other AI company. I don’t really care.

I tell people this: if you’re joining a sub-$50 million company and you’re the CRO, that feels—my opinion is that it feels like an ego play, and it feels like you’re a little bit shortsighted. Eventually, you’re going to stumble, and then what are they going to do? They’re going to say, “Oh, we need to hire a CRO. You’re out,” right? Now you’re not going to learn anything because you’ve shot your shot.

It’s also indicative of a founder. If you’ve got a really strong, solid founder who’s able to hire incredibly well, they’re not going to give premature CRO titles. It’s a real sign of an immature founder.

Interesting. I didn’t think about that, but that’s fair. You protect titles like that because you know it will likely lead to them being demoted in 2 years, then leaving, and then you’ve got another situation. Versus if you come in as head of sales or a go-to-market leader, there’s always room to go up.

How fast do you know when someone you hire is good? If it’s an IC, naturally—I listened to one of your podcasts with someone else, and you were talking about this. How do you know a big-enterprise rep, a big-deals person, is good when they have a 9-month ramp? How are you going to know in month 3 if they’re good or not? For an IC, probably within 3 weeks, right? What are those signs?

The signs are: can they think critically about someone else’s business? That would be the sign of a missed hire, right? You put a prospect in front of them, or you say, “Hey, here’s your target account list. You’ve gone through boot camp, the 2-week boot camp. Here are your 100 accounts. How do you stack-rank them?” If they completely whiff it or say, “I don’t know,” that’s a big red flag.

The second thing is their activity metrics. You just exited boot camp, so first I want to know how they did in boot camp. 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, and how we can help them? Are you hitting send? Are you doing the thing? Are you picking up the phone? Are you hitting send?” If you’re not, you’re not generating pipeline. It means you’re not going to be successful. Those are the early signs that this person isn’t going to work out.

Totally get you. You said “boot camp” quite a few times. I presume we’re not talking about Pilates, which is what my mother will think about. I take my whole team down to Barry’s Bootcamp every day. The kids are bored; we’re pleased.

A lot of founders, especially early-stage founders, really struggle with, “How the hell do I train my reps? I’ve never run a sales team.” What is boot camp, Becca?

That’s a little bit later-stage. When I joined Heap and when I joined dbt, we didn’t have a boot camp.

So, how should early-stage founders train reps?

Here’s what we did at Heap.

Basically, Matteen and Ravi showed that they did the thing. We rode along, and then that shift started to happen: “Okay, now we run the call, and maybe you’re on a few.”

Now you have Gong, so you can actually send the people you hired all of your previous Gong calls. All the founders I work with, I tell them, “Yo, do you have Gong?” If they don’t, I’m like, “Ooh, red flag. You have to go and just buy it, right?”

Then send whoever you hire all of the calls that you’ve done. One, they’re going to give you feedback on how to sell, but two, they’ll hear how you talk about it. That’s the most important thing to me: how do I take what’s in my brain and put it in your brain?

So, if I’m a founder hiring today at an early-stage company under $10 million in revenue, what should I look for in the people that I’m hiring? Just people who press send and have a lot of energy? Remember, this is really early stage. What is that profile?

I keep coming back to thinking critically about your customers. I’ll give you 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 JPMC would use it? Or how the company that they’re currently at would use it and the impact that it has?

What I mean by impact is—I’ll give you an example. Whenever we talk about AI tools, I feel like we talk about the art of the possible, pie-in-the-sky stuff. I’m like, “Hey, hey, hey. Let’s 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 basics: when we’re single-threaded, let’s start there. Let’s help people do the basics well before we get to, “Oh, it automates the outbound, and then it automates the first deck, and then 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.”

When they talk about your widget in the context of their company, are they talking about pie-in-the-sky ideas, or are they saying, “This is actually the real problem that it’s solving for us, and the impact of that real problem is that our forecast is screwed up, we miss our revenue target, or our rep productivity sucks because of it”?

Can they tie your thing to a real business problem that they and other people are facing, and then tie a dollar outcome to it? Those are the types of people that I want. Then I test for, “Okay, do they have the drive?”

Obviously, I’m biased toward having college athletes because they’ve learned how to work hard. All you have to do is teach them how to work smart. If you teach them how to work smart, it’s really tough to teach someone how to work hard.

I think they also have the discipline to do the work when no one is watching. You were an athlete, and I like to think that I am.

Well, you—I don’t know. You showed up with those pretty cool M-Frames.

Thank you so much. Most of the time is spent in a gym with no one else at 5:00 a.m. in the morning, and that black-tie dinner where you hopefully look relatively athletic is once every 6 months, where the world might see that you’re fit. The posts that you post on Instagram now—

Yeah, that’s right. The posts that you post on Instagram now.

Of skipping donut time and skipping everything else. I totally get you.

On the flip side of that, what do you look for? We were going back earlier; we were like, “Oh, the FOMO of late: should I join the AI company or not?” There are so many well-funded AI companies today. They all have shiny VCs, and they all have people who are pronouncing themselves to be replacing work for every large profession.

What would you advise those sales reps who feel like they’ve plateaued—rotting, as you put it nicely—which one should I choose?

That’s honestly really tough. I obviously hadn’t intended to leave dbt, if I’m honest. I was like, “I’m going to finish out the fiscal year, and then maybe I’ll start to think about what’s next.”

Then I met Varun, and you know Varun. We went for multiple walks around the neighborhood. He lives around the corner from me in Brooklyn. I feel like I got a little bit of the cheat code because I do think that Clay is the most compelling company on the planet right now.

When you think about AI companies, a lot of people have—we just hired a RevOps guy, and he’s fantastic. He has this phrase: “Everybody has the Claude spookies.” I’m like, “That’s a really good way to describe it.”

It’s the feeling of, “Well, why wouldn’t Claude just do this? Is Claude going to overtake this market? Is Claude going to put you out of business?” There are a lot of companies out there that I look at and I’m like, “Mm-hmm, I get it. Yeah, I think that could be a thing for you.”

The real answer is, I don’t really know. What I think about is: is there something that’s not just AI that’s defensible?

Clay has this data marketplace. It’s really tough to build that. You could go buy 180 different data providers and build your own, but that’s a lot of work when you think about just buying software to do that for you.

I would look for some sort of other defensibility outside of just, “We’re automating this,” or, “We’re going to automate this profession away,” or, “We’re going to automate a workflow.” There’s not—I can’t even think of a company that I would shout out that’s doing that, right?

But I would say just look for a company with unwavering product-market fit. It’s pretty hard to sell something no one wants.

That is 100% right. It’s pretty easy to sell something that everyone wants.

Yeah. Is it? As someone who is currently selling something that everybody wants, is it easy? It is easy in the beginning, because you could grow as a company 1,000% just by doing the thing, by having moderate execution on your sales process. If you have a really great product, it’s going to fly off the shelves, right?

But as you grow, it becomes very challenging to grow 1,000% year over year or 250% year over year. A lot of what I focused on when I was evaluating Clay was, “Great that you’re landing these logos. How many stick around? How many double their spend with you?”

The metrics that I got—I think I can share—were, “We haven’t churned a customer. Our NDR is close to 200%.” Those are the types of things that, if you’re talking to an AI company, are the biggest green flag, right?

It’s not just, can you sell the thing? It’s, can you make the customer successful, and successful enough that they want to go do more with you?

The whole thing is, today, I don’t know if that matters as much as top-line revenue growth, as ridiculous as that sounds. But if you’re thinking about actual personal wealth accumulation, especially in the short term, if you can go from 1 to 200 in a year—

Yeah.

—like some of the AI companies with worse NDR and worse churn metrics. If you can carry that out for 2 to 3 years on a comp basis from stock, you’ll have secondary opportunities to sell $10 million, $20 million, or $30 million worth.

Maybe. Maybe, right?

When I talk about a really secure business that grows 3–4x, which, by the way, is amazing—

Great, which is incredible.

Just not that.

So you’re like, “It’s amazing, but it’s actually amazing for 2011,” right?

People get caught up in this. We did Lagora and we did Lovable—I mean, 13 months to $100 million in revenue.

Yeah. It’s impressive. It’s impressive. Here’s how I think about it: when people come to me and they’re like, “Should I take this offer? How should I think about this?”

A company—let’s call it Acme Co.—a high-flying, fast-growing AI startup might give you $1 million of stock, and you’re like, “Holy shit, I’m rich. By the way, this is growing so fast, it’s going to be $20 million soon.”

There’s a coefficient that I apply to that of liquidity. How liquid is that? Do they actually do tender offers? I think everybody’s been bitten by a company that’s like, “Oh, we’re growing so fast, and we really care about employee liquidity, so we’re going to do tender offers,” and then never does a tender offer, right?

Now you’re sitting on however much stock you have that is probably life-changing for you. I tell people, “What have they done? Not what they say—what have they done that’s shown they’re going to provide liquidity on that equity?”

Just apply a coefficient to that. If they give you $1 million of equity but they haven’t done anything to allow people to sell, and there are definitely people who’ve been there longer than you, what are they doing with those folks? Maybe you apply 0.3x to that, right?

I’m a founder, and you’re an angel investor in my company. Thank you. You’re advising me.

I don’t know how to do sales comp. How do I pay salespeople? What would you advise me in terms of genuinely how to think about salary and comp? How would you advise me?

We just rolled out a variable compensation plan at Clay, right? Before, everybody was just being paid a salary, whether you were the top performer or the bottom performer.

As a salesperson, I saw that and said, “Huh, okay.” A lot of companies have done that in the early days. Stripe did that in the early days.

And I think, as a founder—in other words, no bonuses?

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

Yeah, yeah. I mean, I did this too. It's stupid.

I saw that and said, “Incredible that it's gotten you this far. Let's figure out how you reward, attract, and retain the right talent.”

I'll give you an example. We just hired a GTME, our version of a rep. You can think of it as a rep and a sales engineer rolled into one. We just hired a GTME out here in London, and I got off a red-eye from JFK and had breakfast with her. The conversation was, “How do we go make $1 million here? How do I W-2 $1 million at Clay? Walk me through the math.”

That's what the best reps want to know. They're like, “I have a target. I'll run as fast as I can toward it. Tell me how to do it.” If you don't have the right math, or you can't 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 hiring what—your first 2 salespeople?

Yeah. Here's what worked at Heap.

Can I be pushy? Do you agree with me? It's stupid not to incentivize performance.

I do, just because I'm an athlete, right?

I honestly think it's arrogance because I don't want you paying that equity too. So, like, good luck.

Well, then that's your point: it has no tenders. I think what it does is it just allows people to hide.

The way that I actually say this to people when they're like, “What? The variable compensation plan? What if—” 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. If you overperform on that number, I'm not going to pay you more. Do you think this is a good deal for you?” [laughter]

It sucks. Most salespeople are like, “Yeah, if I overperform, I want to make more money.” Those are the rules of the road. If I don't hit my number, you're going to fire me.

I understand it. I think the genesis of this is that a lot of these companies don't know how to do comp plans, or they're like, “What if?” So they're like, “This is actually just easier.” I think that's maybe okay in certain areas, but I'll tell you the thing that Todd, who I just hired at Clay, and I did at Heap.

We were the first 2 reps at Heap, and we had a compensation plan that was dead simple. We had a base salary. This was 2015 in San Francisco, and I think our base salary was around $60,000. It was pretty low, I guess, by most standards.

Every deal that we closed, we had to pay back our base salary. Every month, it was about $5,000, so the first $5,000 of revenue was a wash. Beyond that, every dollar that we closed, we got 25%. If it was a 2-year deal, every dollar in that 2-year deal, we got 33%.

I have never run harder at a goal in my life than when I knew I was going to make 25% of every single deal that I closed. It aligned our incentives with the company's incentives very directly, and we sprinted at it.

Then we competed with each other. We'd be like, “Who could do the first $100,000 deal?” “Oh, I got the biggest deal.” “Now I got the biggest deal.” Everybody was celebrating, and everybody was making good money.

That was it. It was simple to administer and very direct. When we built our comp plan at Clay, I felt like it was really easy to make it complicated: “20% of your 20% of your variable is 30%...” I'm just like, “Make it simple.” Then it's easy to understand, easy to administer, and everybody understands the rules of the road.

We have accelerators.

So what do you have, then? You have a quota, obviously.

Our quota-to-OTE ratio is around 7.5, which is quite good, right? Quite high.

I was always brought up in the enterprise world, where 3x to 4x was kind of where you were.

I think below 4x, it's like, yikes, right? I've always been taught 4 to 6. Four is kind of solid; 6 is like, wow, you're doing great.

I think in the AI era, you're seeing somewhere like 6x to 10x, depending on the business, the types of deals, the size of the deals, and who you're selling to. We're at a 7.5x quota-to-OTE ratio today. If it doesn't make sense, we're going to make it make sense. We'll change quotas or change pay—that type of thing.

We have accelerators, as you would imagine.

So sorry, I'm not too fast, which is why I'm a venture capitalist.

Punchy, right? It's punchy.

Punchy?

But I hit the ground running for that one.

Yeah, right. It's punchy, but in the AI era, I feel like we're seeing somewhere like 6x to 10x.

So I need to hit 6x to 8x my salary, yeah?

Yeah.

And then what happens? And then I get what?

Then you get paid more on every dollar that you close. It's an accelerator.

Have you worked at a company where they have accelerators before you hit 100% of your number? I mean, 6x to 8x is quite a lot, and only then I get it? Jesus. You don't want to come work for me.

No, it feels like, “Be the perfect husband, bring me coffee and tea every day for 365 days a year, and only then you might get lucky on the 366th day.” [laughter]

Well, it depends.

I'm exhausted. I've cleaned the house for a year. I've made you dinner every night, and I might get one shag. It's exhausting.

Look, you have your OTE, and we pay pretty competitively, I would say. Above and beyond your quota—and this is actually the argument we're having right now—what are the accelerators?

I spent probably 2 hours in the last 2 days with my RevOps leader, Varun, Kareem, our finance leader, and our strategic finance team discussing what the accelerators should be. My perspective is that if you're overachieving, it should be heavily weighted toward overperformance.

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, we come back to the question: what's the percentage of quota attainment at which you make $1 million? That's the number we're fighting over.

Let's say you have 100 reps. If 60% of them are hitting their number, great—they're making their OTE. But is that a good amount to hit? The culture that I think is best is when you have 60% of people over 100% and 80% over 80%.

You're building a winning culture. People are successful, telling their friends they're having so much fun, and saying, “Very successful—come work here.” You get the best talent. That's a rule of thumb that I like.

Our strategic finance guy was like, “Oh, it was 50% over 100 at my last company.” Great, whatever. You should agree on some percentage of your team being over 100% and a certain percentage being over 80%. If those things are true, it builds the right culture, which is actually really important in sales.

I know when you're setting the wrong goals versus having the right team, because 2 different people could say, “We have too-high expectations.” Or it could be that you're just hiring the wrong people.

Yeah, and usually you can tell by the reaction.

Coming back to Heap, they hired both Todd and me at roughly the same time. I think Todd was 3 or 4 months ahead of me. They told us a year later, “We hired you 2 at the same time. We figured we were probably going to fire 1 and keep the better one, but you were both really good, so we kept you both.” I was like, “Oh, okay. Well, thanks.”

I tell every founder this: hire 2 at a time because then you'll actually see whether one is good and one is bad. That's how you do it. Let's say you have 100 reps. There are going to be 5 who just about hit quota. But if you dig under the covers, they're probably not doing the work to be successful, and those are the people you probably don't want on the team.

Well, I'm an investor as well. I was in Vienna the other day trying to lead a Series A, which I did.

Thank you.

I'm leading a very glamorous life. It's not just short shorts.

We went into this office, and there was a sales leaderboard. It had, I don't know, 8 reps at a Series A, early-stage company. My partner at the firm and I were like, “Oh, yeah, we like this.” We felt the competition, and we felt that they were all looking at their numbers. They were on every new deal, every pipe.

That's coming to our sales floor, right? We've hired nontraditional salespeople, so you have to incrementally introduce some of these concepts. But you better believe we're going to build the sales dashboard: how much revenue have we 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 to be at the top on the revenue dashboard, right?

100%. Is there anything we can do to inspire that competitiveness within sales teams, to make them incentivized and encouraged to fight between themselves? The Hunger Games of sales.

Well, I don't actually think so. That's why, if you create a zero-sum game, everybody's just looking out for themselves and they're very scared. That's why I was like, 60% over 100%, 80 over 80 creates this culture where people are excited to help each other and excited to celebrate everybody else's success.

Think back to me and Todd. To be fair, for the record, I closed the first six-figure deal at Heap. And then he was like, "Awesome. I want to go do that, too. Okay, I'm going to go get a bigger one." "Go get a bigger one. Go get a bigger one." We'd be bouncing ideas off each other the whole time. We wanted to help each other because we knew we were building this thing together, but we were like, "I want to go beat you," right?

Even at dbt, which is an open-source product and open-source company, very open-source-minded, it's a different approach. You're giving away software for free and then you're also trying to charge for it, which is kind of a weird dance to do.

Once you get big enough, you do teams, right? The last year that I was there, the central team closed the biggest deal in history. The EMEA team's like, "Well, we need to go get Siemens or Allianz. We need to go get a bigger deal there." You kind of pit people against each other in a fun way.

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." You're fighting over market share, right? Then I would go to the Americas team and say, "Hey, make sure that he doesn't get any more points. Your goal is actually that he goes from 34% to 33%." You put a little chip on people's shoulder, but in a fun way.

I totally get it—just kind of demoralize them in a really fun way.

It's not demoralizing if the company's growing. If the company's growing 3 to 4 times, as you just told me, it's less and less important.

But you feel good about it.

So, we have 6 to 8 times quota. What happens then with the accelerators? If I pay you 10 cents on the dollar before—

Yeah, it should jump pretty high.

—a new deal at Clay, do I get 25%?

It doesn't jump up that high. You know what? I know, I'm very disappointing.

Why did it at Heap and not at Clay?

We did it at Heap because we were the first 2 reps, and they were like—

So, you don't have that higher rate with scale?

I think it depends on the economics of your business. If you think about Clay, we pay for the data that we sell. We pay per credit in the same way that we charge for a credit of data. 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 margins.

I've worked for companies that have less-than-ideal margins, and it compresses what you can actually pay. Maybe that's something that you look for in the AI era: good margins.

Yeah. I don't actually know why we can't do that. There's some sort of flat pay where you have a base commission rate, and then on top of that you get accelerators, right? All Heap did was jump straight to the accelerators and say you have an artificially low base. Now go work your ass off. I like it.

One thing that you said there, about not quite margins with AI companies: a lot of them don't have great margins because they also give a lot up front.

That's right.

And in a sense, is that kind of sales and marketing cost in some ways? How does your job change when people have tried the product already, they've got usage already, and it's not the SDR outbound that it used to be?

I think if you're talking about a PLG motion, and if you have usage, your job then becomes: what are the next use cases? What are the next teams? You're fighting over workloads rather than going and landing a logo.

Think about Salesforce. How many entry points are there for different AI tools? How much market share internally at Salesforce do they have? If you go land a logo—let's say Salesforce is on a PLG motion for your AI widget, and you have 3 people in the marketing team using it, 3 people in the sales team, whatever—your job 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?

Once they're in, you're fighting with them over workloads versus fighting with inertia. It's almost like, can you go into an account and suck the oxygen out? That's actually how I think PLG businesses do really, really well. Someone comes in and they're dabbling in the product, and you as a seller are like, "I'm going to market that internally at that account to all the other people, pick up all the other use cases, and secure the borders of that—not to be too American—from anybody else." It's like Risk, right?

You're thinking about going and securing your land in that account so that other competitors can't come in. You saw this with Snowflake and Databricks. 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 going to win that.

Trump would be proud.

How do you build internal champions within businesses? What's your biggest lesson?

If you actually ask anybody on my team—I hope they don't listen to this because they're going to groan—I will often just say, "Okay, who do you have as a champion?" And they're like, "I have a—yeah, I got this person, my champion." I'm like, "What are the 3 characteristics of a champion?" All of them know: 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 3 things, honestly, just the personal win—"Why are you doing this?"

The win is that they personally gain from your tool benefiting their company.

I'll give an example of a champion of Clay at a company that we all would know. Her win is, "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. I'm building my personal brand, and I want to get into venture and investing and advising companies on AI. I'm leveraging what I'm doing with Clay to show that I'm that person." I'm like, "That's an incredible personal win."

At dbt, you would talk to folks and be like, "Why do you care so much about this? Is this just data transformation?" They'd be like, "But I want to be the data guy. I want to be the guy that owns the entire data stack and does all this cool stuff. Then, when I leave this company, I can go to another company and be the data guy and come in with a higher salary, get more equity, whatever."

If you focus on that, if you can get to that, you probably have a champion, and they're probably going to go to war for you. They have to have the other 2 things.

Becca, I'm one of your reps. I'm sorry, Becca. It just slipped to next quarter. I know I said this quarter. I know I said this quarter, but Mitsubishi—they just—

That never happens.

That never happens, but Mitsubishi—they just—I just slipped to next quarter. What do you say to me?

Well, I'd start with why. Why did it slip?

Honestly, they took longer to get back to me than I thought, and we just didn't get it over the line.

Here's a big one. This actually happened to one of my reps: "I 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."

I'm like, "Okay, let's break this down. Is there someone internally who could have told us that?" "Yes, probably." So then, did we talk to that person? Did you talk to that person? Did you ask the right question? Because those are 2 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 that's your procurement's job, right?

Then I go to, "Okay, who's your champion? Do you have a champion?" And often what I'll hear is someone mistaking a coach for a champion, or a person who's dabbling in the software for a champion.

They assume it’s the champion, versus—I always use this when I say, “What have you seen with your two eyes that tells you this person’s a champion?” Right? That they have those 3 attributes. What have you seen with your 2 eyes? People make fun of me, but they remember, and now they’ve gotten better at it.

We just opened a London office. I was talking to one of the GTM-ers out here, and she was like, “Oh, well, yeah, yeah, he’s a bad champion.” I’m like, “Whoa, whoa, whoa, hold on here.” You have to be meticulous and kind of an ass about it when people say, “Qualify champion.” I’m like, “No, no, no, it’s binary.” You’re either a champion or you’re not a champion.

Let’s be really clear about it. If you say they’re a champion, what have you seen with your 2 eyes that tells you they’re selling for you when you’re not in the room, that they have access and influence over the EB, and that there’s a personal win? It’s pretty simple. If you don’t have a champion, you’re probably not going 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 they were your champion, and you probably didn’t do the best job.

When we sit down and do postmortems and collaborative forecasting on what we’ve done and what we have ahead of us, how often do we do that? Every week on Thursdays, every one of my front-line managers goes and does a forecast call with their team. They either do it as a team or 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?”

Then it’s, “Okay, what metric is attached to that pain? Who gives a shit about that metric? Are we talking to them?” These types of questions help us understand: Do you have control of the deal? Is the deal in the right stage? Are we making assumptions?

Do we need to go back and actually get to the end? Something happens, and you’re like, “I have a bad champion.” Well, actually, you’re back here and you skipped a couple of steps. Let’s just be real and move it back there now, and go do the work to actually build the right deal.

We do that once a week. I do that with my front-line 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. I expect that they’re in the deals in the same way that I’m running a couple of deals with reps. It’s a lot of fun.

What are the biggest mistakes sales leaders make in forecasting?

I think, at the front line, it’s not being in the details—not being in the deals with the rep. I’ll give you an example. I talked about John Dalton earlier. John Dalton is one of my favorite people. I would love to work with John Dalton for the rest of my life. He also lives in Santa Barbara, so he’s very chill.

John Dalton, if you asked him, “Hey, what’s going on with the company?” he knows, because he’s in the deal with the rep, doing the work and 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. We have a call on Friday to talk about all the approval processes and the signing process.”

Versus, you might ask Stacy, “Hey, what’s going on with the company?” and she’s like, “Let me check my notes. The last update…” I’m like, “I can read the update in Salesforce.” We have a specific, standardized way of writing your next steps. I can go read that, too. But what is your perspective on the deal? Are you in the deal?

Not every front-line manager can be in every single deal, so you have to choose which ones are the most important. It’s usually a factor of how tenured the rep is, how good the rep is, what we’re trying to develop with them, whether it’s a high-profile deal, whether it’s a great logo that we can go and expand, or whether it’s the biggest deal. However you decide, you decide. That’s probably the biggest mistake that I see from front-line leaders.

We get that big logo. Yeah, I never forget what someone told me on the show once: “You never want your farmer going against someone else’s hunter.”

How do you think about maintaining that relationship with the rep who’s a hunter versus handing off to pushy, cushy, nice CS, and then one of your competitors’ hunters is going after the same workflow in your account because you didn’t secure the account? You’ve got cushy CS who’s now like, “Oh, softly, softly,” and the hunter’s going hard.

I mean, look, you’re getting into the question of what the model of the go-to-market team is. I’ve been in models where you do a full handoff, and I’ve been in models where you do a handoff and keep it for 12 months, whatever. My favorite model is: you sell the deal, you renew the deal, and you’re comped on net dollars.

What that does is incentivize the rep to sell a good deal and protect your unit economics. Someone on John’s team sold a deal that was slightly above list price. They had a much easier time than the rep that discounted 40% and is trying to claw that back now.

It helps protect the unit economics because you know that you’re going to want to go and expand that. But, 2, you sell a shitty deal, you’re going to renew that shitty deal, and you’re probably going to take some churn or contraction. That’s actually the model that I love because it incentivizes you, the hunter, to go and secure the border in that account and not let anybody else come take your workflows.

You look at Snowflake or Databricks—that’s their model—and it’s because they’re competing over workflows in the account. It’s the same for us.

You said, “Oh, the discount, then you have to make it up over time.” Discounting is a great way to stop what I said earlier about, “Oh, it slipped into next quarter.” It encourages urgency: “I’ll give you a discount if you sign.”

We don’t like discounting, and I 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 1?” I was like, “Fair play.”

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.

When we buy software, the rep is 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.” I’m going to move fast because I need it. We bought a forecasting tool. I need this because I have no control over the business and no visibility into what’s happening. I need this more than you need to sell this deal.

Sure, I’ll take your discount, but we’re going to try to get this deal done before next Friday. 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, ‘How do I help get this in your hands faster?’” If they say, “I don’t really care about it,” you probably skipped a step. Let’s go back and figure it out.

You said you buy software. I’m friends with Jason Lemkin from SaaStr. He said, “I just got rid of a lot of my team, including a lot of my sales team. We have AI SDRs, Outreach, Qualified, and Moniker now. I don’t need them. I’m doing more. I’m doing better with less.”

How does the world change with AI SDRs? Are SDRs dead? Is outbound dead?

Absolutely not. No way. When I first started Clay, people asked, “SDRs—what’s your perspective?” I was like, “I’m building an SDR team. I’m building a Clay SDR team.” 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.

It might be efficient when you’re trying to generate $40 million of pipeline because you have, I don’t know, a $10 million or $15 million revenue target. But when you get into having to build $250 million of pipeline, it’s probably a little bit more efficient to put some hungry, scrappy 24-year-old on the field, pay them a certain amount of money, and say, “Go run at these accounts.”

The second thing is: If you don’t have an SDR team, who the hell are you going to promote into your closing roles? It’s really de-risked if you have an SDR that you’re promoting. Those are the best people. So, outbound is not dead. No, outbound is not dead.

Should AEs be responsible for pipeline generation?

Everybody should be responsible for pipeline generation. Everybody owns pipeline. We have what we call Clay Day on Tuesdays.

You might know it by its former name, PG Tuesday.

Yeah. Every Tuesday, I ask my team, “Who can I reach out to for you?” We have a whole channel called “multi-threading requests.” Who can Varun, Kareem, or our chief of staff, Julia, 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 funny—just the same message coming from a different mouth totally changes everything.

Yeah. It gets a completely different response. I encourage people to think about it. One of the GTMs I was talking to out here in London—Tuesday rolls around, we kick off Clay Day, and 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 think about all the ways I can make contact with them. Is it a VC? Is it me? Is it you? Is it our partners?”

You get a Sequoia partner to LinkedIn-message a CEO, and it 100% has an increased chance of getting a response.

Yes, 100%.

One of our portfolio companies—the CRO comes in monthly and gives me the top 10 targets, and I just go with them to the CEOs on LinkedIn. I have a blue check mark and lots of followers on LinkedIn.

Yeah, I know. Important. I heard—very important channel on LinkedIn. Nine out of 10 respond.

Yeah, and they’re like one out of 10. Totally different. I completely agree with you. So yes, 100%. You said something really interesting: everyone at Clay is a social media star. Do you encourage your reps to be public online? We had the head of growth at Lovable on, and she said, “The best form of marketing is employee-led marketing.”

Yeah. I think we do. I tell people I need to be better at this—I need to follow my own advice. We do really cool things at Clay. For example, if you work at Clay and want to try a new AI tool, you can 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, 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 a lot of other companies that are like—

“These are approvals. It needs to go through our AI council, they need to evaluate it, and we’ll get back to you never. How’s that?”

And so things like that, I’m like, “Whoa. You should actually post about that,” because that’s something no other company is doing. Anybody who’s out there and sees that and is currently rotting at their company is like, “Holy shit, I want to do that.”

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

You said AI doesn’t change SDRs. It doesn’t change outbound. What does it change?

Well, I wouldn’t say that it doesn’t change it. I just said it doesn’t replace it. If I can—and this is my thesis with the Clay SDR team—let’s say in 2018 an SDR can book 15 meetings in a given month. If I can arm that rep with Clay and a Clay seat, maybe a Lovable seat, I can tool them with some sort of AI stack, and now they can book 40 meetings a month, I’m going to say, “Yes, please. Thank you.”

Now I want to grow my team of SDRs from 8 to infinity because I see a ton more productivity. Anybody who’s like, “We’re just going to cut our SDR team in half,” I’m like, “Hmm, okay. That’s an interesting move.” That’s a scared play that you’re making, because you’re saying, “I can get the same productivity for half,” versus saying, “I can get this productivity, and now I’m going to multiply that into infinity and take all the space, all the oxygen, out of these accounts.”

Unless one assumes that you need the SDR for part of the work, and the other assumes that you can replace it entirely and just hand it off to an AE.

If you think you can replace it entirely and just hand it off to an AE, you can get to infinity with one tool.

How many businesses do you think out there can actually replace the entire SDR process and just hand it off to an AE?

Right now, none. So you’re going to have some number of SDRs.

What’s been the best AI tool that you’ve brought into the company from a sales perspective?

I don’t know that I have particularly found an AI tool and brought it in, but here are 2 tools that we use pretty aggressively. Everybody uses Lovable, everybody uses Clay. I was talking last night with a bunch of my team about how, on the plane back to New York, I’m probably just going to look at Claude’s saved projects and steal a bunch of ideas.

The 2 tools I’m obsessed with right now are Granola. Everybody’s obsessed with Granola. They just founded the company and raised a big round, and I’m happy for them. The other tool is WhisperFlow. Are you familiar with it?

No. This is very personal, sir. Granola—I was the first VC they met, and I turned them down. I sent my partner a note saying, “Someone should set up a JustGiving page for them, because no one would give them money.”

Chris is a friend of mine, and he basically came to me and was like, “AI and notes—it’s going to be a thing. I don’t have any clue how, what, where, or when, but that’s the thing.” I’ve been in Rome research, I’ve been in all the others.

But you 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. I sent it to Varun and my talent partner, and it’s very cut-and-dry—there’s no emotion in the Granola notes.

Varun was like, “Is this a positive? Was this a positive reference?” and I was like, “Yes, it was glowing.” I looked back at the Granola notes, and it was just objective: “Yes, Stacy helped me in this deal,” and so on. I was like, “Okay, got it. I’ll figure out a different process.” They have some things to work on.

WhisperFlow, to be fair, I never had the chance to mess with them, but I love them. I use them the whole freaking time. I never type anymore. The only thing that really annoys me on the phone is the toggle.

Yeah, that is kind of annoying, especially if you don’t have it open.

Yeah. Wispr Flow, if you could fix that for me, that would be really great.

I love that. I’m with you. I don’t know if you have this problem, but if I open a new email tab and just have a blank email, I’m like, “Oh my God, what am I going to say?” If I can just press a button and say, “Yo, squad, this is what’s going on this week. Here are the numbers, here’s the pipeline,” and so on, it does the whole thing for me, and I just hyperlink the whole thing.

You can add a little bit if you like: “Ah, I didn’t want to say—”

Yeah, yeah. So I think that that’s—

Hard emails, ironically, where it’s difficult to know what to type. It’s easier to know what to say.

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

I remember interviewing him when he was at Pendo.

Oh, yeah. I have a ton of respect for him, and if you’ve been an operator that long, God, you’ve got some thick skin. He said the other day, “No one’s going to type anymore. If you’re typing, you’re behind. You should be talking to your technology.”

I was like, “That’s a weird way to think about it. It’s a very futuristic, Jetsons way to think about it, but it’s actually true.” I don’t type that much anymore.

Never. Yeah, I completely agree. But you haven’t used the AI sales tools to boost productivity? You’re not pushing them?

I mean, we use Clay. We use Clay to supercharge our SDR team, because if I can build a system that tells the SDR where to focus, and then I can go train that SDR, “Don’t be a dick.” It’s not intuitive. It’s not that easy. I’ve—

Well, I’ve tried. Bruno and Bruno keep on trying to get me to do stuff.

And I’m trying. It’s a bit complex.

I don’t know where to start.

Well, actually, it’s a bit of a blank-page problem.

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

With WhisperFlow, it’s like, “Just talk.” I can’t just verbal-diarrhea Clay.

You can now.

Well, you can’t verbal—

You can type-diarrhea.

Maybe, yeah. You can use WhisperFlow into Sculptor, which is our kind of Clippy.

Yeah, from 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 their Yelp reviews are, and what people are actually saying in those Yelp reviews is the best dish. 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 from a blank page, because that was when I was interviewing or talking to Varun about joining Clay. There were a bunch of things where I was like, “Hey, and what about this?” My wife uses Clay, or we bought Clay at dbt. “What about this? This is a gap.” And he’d be like, “Yeah, we did.”

I’d be like, “Yo, this is a blank-page problem. How do you start that?” And he was like, “We’re actually building it.” Again, come on. Is that not Claude-ified? Is that not something Claude would just do?

You could probably use Claude to say, “Hey, give me the top 50 oil companies in Austin. Find the CEOs of all of them. Get me their email for each of them. Actually, open up Clay on that one straight away.” They’re like, “No, we don’t provide emails.”

Well, I think that was useful. But think about it: 1 rep could do that. How do you do that when you have 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. They’re like, “Why doesn’t Claude just do that?” It’s like, “Hey, have you ever tried to get 100 people to do something different, to change something, to iterate in the same way that you iterate?” Good luck. It’s hard.

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

I totally get that. Listen, I could talk to you all day. I want to move to a quick-fire round. I’ll say a short statement, and you give me your immediate thoughts. Does that sound good?

Okay, yeah. We’ll do our best.

What’s the worst hiring mistake sales leaders make?

Focusing on the last company that they were at and whether it was a playbook company or not. I’ll give an example. It’s actually interesting: I don’t know if you saw that Brian McCarthy just joined Cursor from Rubrik, right? I was texting with a friend last night, and a lot of people are now moving from Rubrik to Cursor.

Rubrik is a very playbook-driven company. Cursor is an AI-first company. I have a ton of respect for those guys and all the playbook folks. What they’ve done and what they’ve taught the craft of sales is really valuable. It’s going to be very interesting to see how they modify their playbook to be AI-first, because I think there are a lot of parts that are still very relevant, but there are some parts that are going to be thrown out.

I’ll give an example: understanding the entire business case before you do anything in the product or show any value. You can’t really sell that way in the AI space, so I’m very interested to see how that works. I’ve worked for leaders in the past who have a certain hiring profile and do not want to deviate from that, even for high-slope individuals. I think that’s a mistake, because then you just get 100 of the same kind of person instead of people who are actually going to push the envelope.

What have you changed your mind on in the last 12 months?

12 months ago, I actively resisted using AI. I thought it was going to make people dumber. You see some folks who just ask Claude for the answer rather than reasoning about it themselves, and I didn’t love that.

Obviously, now I work at an AI company, so maybe I’m a hypocrite. Basically, I went from saying, “I’m not going to use this thing. I’ve got a brain, and I’m going to use it,” to, “Okay, how can I offload some of the things? How can I teach Claude to think like me so that I have 2 of me and can converse with myself and be my own thought partner?”

Do sales teams have to be in person?

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

Office.

I think you get so much more when you’re working in person with your team. I’m a 5-day-a-weeker. I show up to the office 5 days a week. I’m here in London for these 4 days, and tomorrow I’m going to go to the office on Friday. I get FOMO when I’m not in the office.

You know what pisses me off? When you go in and other people aren’t in. Friday is the new holiday now, especially in Europe. Friday is a work-from-home Friday.

It’s not work-from-home Friday. I would never let work-from-home Friday—or Monday—basically be a new weekend. I don’t track attendance. 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 going to have a conversation.

What would you most like to change about the world of sales?

I think everybody would say this: people feel like they don’t want to be sellers. 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 wish people would view sales more like this: “Hey, we’re not just making 150 cold calls a day and indiscriminately trying to sling our product. I actually thought critically about your business, and here’s how I can help you.” I understand there are a lot of us out here, but I wish people would view sales more that way.

When is the right time to verticalize sales teams?

You asked about critically thinking about a business. I’ll tell you how we’re thinking about it at Clari. We’re going to spin out a small new-verticals team, and the reason 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 for where we land or the story that we tell.

I think when you’re trying to enter a new vertical in a concerted way, that’s when it makes sense. I also think it makes sense when there’s some sort of expertise that you need. Everybody has a finance vertical, or they hire someone in Detroit to sell to the big auto companies. If there’s some sort of differentiated expertise, that makes sense.

Yeah, I think that makes sense. Here’s where it doesn’t make sense: “I’ve got my guy at JPMC, and he just buys whatever.” That’s dead. The relationship type of sale—“I know all these people; I have this Rolodex”—is gone, because I think today the buying cycle and the buying committee are not just 1 person. You have to have the product that can satisfy the needs of multiple people in multiple divisions in a business.

What ACV is justified for a sales rep?

Ooh. You see lots of PLG tools that are super cheap, and you’re like, “Well, they could expand, but they could not.” There’s a math equation in there that I don’t know the intricacies of. I’m not a math major.

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?” If it’s not a very short sales cycle, I’ll talk to some founders and they’ll say, “Our average deal size is $25K, and our deal length is 6 months.” I’m like, “What are we doing here, guys?” You’re either spending way too much time with these folks, or you could add at least another 0 and justify it.

You talk to HubSpot, and they’re at the size where they’ve got reps working $9,000 deals. They’re at a different scale. They can do it light-touch, with a lot at the same time.

Yeah, right? They’re like, “Our average deal size is $9,000 MRR, and we do a 3-call close. We’re just focused on logo acquisition because we know that we can go double those.” Cool. That makes sense from a business perspective.

What’s your favorite win story of a deal?

I worked on a deal with a rep at my last company. It was a large bank in Australia, one of the big 4 banks. We had an EB. She was the chief digital officer and chief data officer, and she just got it. She was maybe a little earlier in her career for a C-level role, but she was super innovative.

She would come to us and be like, “I’m checking out these other tools. What do you guys think? How do they play? Does this story make sense?” It was almost like working with a friend who was really smart and putting together their data stack.

The use case was the coolest, though. They were using our product to basically create new derivatives that they were going to sell to my classification of poor rich people—people who had between $10 million and $50 million of net worth. They were going to launch 10 of these products, and they were expecting each of those products to generate $100 million for them.

I was like, “Wow. You’ve critically thought about this.” We kind of uncovered all that and helped them build the business case, but it was a very intricate use case that had a huge financial impact, and it was just a fun team.

My favorite deals are not the biggest deals. It’s the deals where I’m working on one right now with one of the GTM-ers on my team. I show up to the calls, and we have our plan. We know what we’re trying to do. We need to drive these steps.

But the people on the other end of the phone are 2 women who clearly have their shit together, and they’re like, “We need to make a big change in this company, and 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?

You’re thinking about it exactly the right way, Christie. You’re doing great.

What’s the biggest deal you’ve ever closed?

Me personally?

Yeah.

It was $1.1 million for 3 years, so $3.3 million TCV with a large financial services company.

Love it. Yeah, that’s a good day. That’s a good day. What’s your biggest advice to a new parent?

The best advice to a new parent—actually, my wife and I talk about this all the time—is that 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.”

There’s no way to get off schedule and no way to feel down about yourself or feel down about the kid. You just go with the flow. It makes your life a little easier.

Mark Henry has a reason why he called that retail therapy. La la la, life do its thing, and you’re like, “You know what? It did its thing.”

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

I love that. That’s amazing. Listen, it’s been so fun to do this. Thank you so much for being so amazing, and I’ve loved having you on.

Thank you for having me. Really enjoyed it.