# Scaling Sales Orgs: AI, Compensation, and Deal Hygiene

**Podcast:** The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
**Published:** 2026-05-02

## Transcript

How do you read a LinkedIn profile?
Our quota to OT ratio is like, I think it's like seven and a half.
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.
I think is best is when you have 60% of people over 100%, 80% over 80%.
You're building a winning culture.
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.
Outbound will never be dead.
This is 20 Sales with me, Harry Stebbings.
20 Sales is the monthly show where we sit down with the best sales leaders to unpack their tips, tactics, and strategies to scaling the best sales orgs.
Today, we have Becca Lindquist, head of sales at Clay.
Clay is one of the fastest growing companies to scale to $100 million in ARR.
And honestly, I've interviewed 100 of the best sales leaders now.
I would say Becca and Carles Rayner at Eleven Labs are the two that I have been...
most impressed by this was an exceptional deep dive that goes very granular into how to scale a sales org get your pen and paper out you'll be taking a lot of notes in this one But before we dive into the show today, a quick shout out to a company I've been genuinely blown away by and have been tracking closely, ROX.
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Becker, it is so good to have you in the studio.
It's so nice to do it in person.
I went for a walk around High Park with Varun, and he said so many wonderful things.
So thank you so much for joining me today.
Thanks for having me.
Now, I think a lot of sales leaders and salespeople are looking at themselves today going, am I in the right place?
You're in a SaaS company, and you're like, that's not an AI company.
And you're seeing a load of friends make a lot of money at AI companies.
How should people actually think about the decision of, should I leave my SaaS company and join a hot AI company, or should I actually just stay?
So I have a lot of these types of conversations, both with peers and with folks that are having this like 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 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 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, 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.
So what do you do when you feel as a sales rep or leader?
Yeah.
that you are rotting what do you do you gotta go you gotta go find something else right you can't reinvigorate it ah i mean maybe you can move maybe you can move into like a different role or like a different sub sector 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 like innovate meaningfully i mean maybe you could go run the company's like 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 like partially why I joined Clay, right?
Like if you leave a company like that and you go to a next gen AI startup, you're going 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 going to stay there but like most people are companies for like four or five years did comment if you've been at salesforce for 12 13 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 kind of melee of mediocrity for 12 13 14 years is that a bad read I don't think it's a bad read.
I actually, so we're recruiting a lot right now at Clay.
And, you know, I see a lot of profiles.
I actually ran a training for my team on recruiting last week, the week before.
And one of the things that we talked about is like, how do you read a LinkedIn profile?
Oh, wow.
Right.
And we just pulled up people's LinkedIn's.
We pulled up yours.
It was actually really weird.
We were like, don't hire this guy.
No, I'm kidding.
Terrible.
Look at that.
Egotistical, arrogant.
Why would I?
He's a diva.
Next.
So we pull up 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?
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?
What is that amount of time?
Because I also hate the bouncer.
The biggest red flag for me is 13 months here, 15 months here.
There's a lower bound too, and I think it's two years, right?
I always think four to five years is optimal.
Yeah.
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 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 of 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 got to like, I don't know, redo the laces and the insoles all screwed up.
Like, I think it's really tough for someone who's been in a company that long to like adjust and prove me wrong.
Right.
Like I have a friend who is at Heap, which I was at.
two companies ago right he was there for like eight or nine years and i'd actually like every time that you know the linkedin anniversary it's like oh my god 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 to come to 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 so denigrative.
I love that.
That's so funny.
Training, recruiting.
Take me to that day.
On the LinkedIn specifically, is there anything else we watch out for?
Don't laugh.
One of my big red flies is someone who has a picture of them speaking at an event.
It just tells me that they have great self-importance.
You're just a dick.
Well, actually, 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 them speaking at a wedding.
And you can tell.
Oh, wow.
That's bleak.
That's really sad.
And then like, you know, look, 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.
And like, you know, you look at my LinkedIn.
Lucky you're on a podcast.
Yeah, yeah, yeah.
So yeah, great, great, great job here, right?
But like, you know, I look at my LinkedIn and 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.
I just discount that.
Any big green flags?
Like for me, data centricity is really helpful.
So if you talk about your heap experience and you're like, I drove 387% increase in SDR volume, whatever it is, or pipe or.
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.
When I look at someone's LinkedIn and I can't tell the story for them.
So like, I'll give an example.
All companies that 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 what's the story?
Where's the expertise that you're building?
Can you explain that to me?
You want aligned companies where you see...
aligned knowledge growing in that sector a little bit like think about there was a guy that worked for me i actually think i gave you his uh contact info his name is 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 am 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 cloud, 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.
So that's so interesting you say that.
I 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 the knowledge on contract size.
I'd rather someone who's dealt with large enterprise before than someone who's worked in databases before.
I don't know about that.
I think about everybody that we've hired at Clay.
We've hired kind of non-traditional 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 in 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 want 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 was doing it in every single deal.
And that just gave me the confidence to say, I'm going to invest in this person.
Came to me a year and a half later and was like, put me into this role.
I can do it.
And I was like, okay, let's go do it together.
And 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, the 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.
When you've made a bad hire, what did you not see that you should have seen?
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, okay, probably not going to work.
So this is feedback in the job interview?
Yeah.
I'll give an example.
I hired a guy in San Francisco who I'm really excited about.
He went on a walk with Varun.
Varun called me after, gave me a voice note and gave me some feedback.
So I just called him and I was like, hey, how do you think it went?
I'm like, okay, great, great, great.
Hey, this is something that I got.
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 going to be like to work with that person.
If they're like, oh, well, like, oh, he didn't really say that.
Oh, interesting.
OK.
But if they're like, OK, 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 company like Clay, where we're like, I don't know, building something new.
There's a lot of like open white space.
If someone's really defensive, that's actually the biggest red flag.
And we need to incorporate it into the rep interview.
I made a hire one time ever since.
I've kind of just said, okay, I'm going to 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 your girlfriend or your wife to a restaurant and you see how they treat the hostess and the waiter.
One of the biggest signs I look for.
If it's bad, I'm out.
Right?
Yeah.
It's the same thing.
So if the recruiter gives them feedback and they're just, they treat the recruiter a certain kind of way, I'm out.
You know, the one thing I've learned on hiring as well is when they push on title, they're bad.
When they push on salary, they tend to be good and know their worth.
It's really all my mishires are when I'm not happy being a EA.
I want to be a chief of staff.
You're an EA.
I agree.
You're happy with the salary, so you're not going to that, but it's actually that.
always a mistake when i don't care about title but i'm worth more yeah that's when i make mistakes that's that's actually that's if you think about so like we talked about todd right same same me and todd we agree on that i was like i actually don't really care what my title is i do care how much you pay me i care about scope but like 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 50 million dollar company and you're the cro I'm like, that feels, my opinion, feels like an ego play.
And it feels like you are a little bit short-sighted because 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, right?
I think 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.
Yeah, that's fair.
It's a real sign of a...
immature founder.
Interesting.
I didn't think about that, but that's fair.
You protect titles like that because you know it will lead to them likely being demoted in two years and then leaving and then you've got another shit situation.
Versus if you come in as like, I don't know, head of sales or like gold market leader, whatever, right?
There's always room to go up.
How fast do you know when someone shit that you hire?
If it's nice to see it, and actually I listened to one of your pod...
podcast 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 the fuck are you gonna know in month three if they're good or not right do 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 that would be like the sign of a mishire.
You put a prospect in front of them or you say, hey, here's your target account list.
You've gone through bootcamp, the two-week bootcamp.
Here's your hundred accounts.
How do you stack rank them?
And they just completely whiff it.
Or they're like, I don't know, right?
Like, ooh, that's a big red flag.
The second thing is like, what are their activity metrics, right?
Like, okay, you just exited bootcamp.
First, I want to know how they did in bootcamp.
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 going to be successful, right?
So those are the early flags of like, this person's not going to work out.
Totally get it.
You said that bootcamp quite a few times.
Yeah, yeah.
I presume we're not talking about Pilates, which is what my mother will think about.
Yeah, I take my whole team down to various bootcamps every day.
It's like, whoa, kids are a boy will be pleased.
No, like a lot of founders really struggle with it, especially early founders.
Like, how the fuck do I train my reps?
I've never run a sales.
What is bootcamp, Becca?
That's a little bit later stage thing.
When I joined Heap and when I joined DBT, we didn't have a bootcamp.
So how should early stage founders train reps?
So 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, OK, 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, oh, red flag.
You got to go just go get just buy it and then send whoever you hire all of the calls that you've done.
Because they're going to, one, they're going to give you feedback on like how to sell, but two, they'll hear how you talk about it.
And that's actually the most, like 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?
So if I'm a founder hiring today, early stage company, under 10 million in revenue, what should I look for in the people that I'm hiring?
Just people that press send and have a lot of energy.
And remember this really early stage, what is that profile?
I keep coming back to like thinking critically about your customers.
So 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 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 is that i don't know our forecast is is screwed up or we miss our revenue target or like our rep productivity sucks because of it can they tie can they tie your your thing to a real business problem that they are facing and other people are facing and then tie a dollar outcome to it.
Like 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 learned how to work hard.
All you got 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.
Yeah, that's true.
You're an athlete and I like to think that I am.
I don't know.
You shut up with those pretty cool M frames.
Thank you so much.
But most of the time is spent in a gym with no one else at 5 a.m.
in the morning.
And that black tie dinner where you hopefully look relatively athletic is once every six months where the world might see that you're fit.
Yeah, that's right.
But that's it.
That's right.
The posts are the things you post on Instagram.
Yeah, yeah, yeah.
of skipping donut time and skipping everything else i totally get you on the flip side of that what you look for we were going back earlier we were like oh the fomo of like oh should i join an ai company or not there are so many well-funded ai companies today i know and they will have shiny vcs and they will 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 they're rotting nicely which one should i choose Honestly, it's really tough.
And, like, I obviously, like, I hadn't intended to leave DBT, if I'm honest.
Like, I was like, I'm going to finish out the fiscal year, and then maybe I'll start to think about what's next.
And I met Varun, and you know Varun.
We went for multiple walks around.
He lives around the corner from me in Brooklyn.
feel like I got a little bit of the cheat code because 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 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 feeling of like, well, why wouldn't Claude just do this?
Is Claude going to overtake this market?
Is Claude going to put you out of business?
Right.
And it's like, there's a lot of companies out there that I look at and I'm like.
Yeah, I think that that could be a thing for you.
The real answer is 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 tough to build that.
Yeah, you could go do 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.
And so I would look for some sort of other defensibility outside of just, we're automating this, or we're going to automate this professional way, or a workflow.
And that's a really tough thing to find.
I can't even think of a company that I would shout out that's doing that, right?
I totally get that.
I would say just look for a company with unwavering product market fit.
It's pretty hard to sell shit no one wants.
That is 100% right.
And it's pretty easy to sell shit that everyone wants.
Is it?
As someone who is currently selling shit that everybody wants, yeah.
Is it easy?
It is easy in the beginning because you could grow as a company 1,000% just by doing the thing, like having a moderate.
execution on your sales process.
And 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, 250% year over year, right?
So a lot of what I focused on when I was evaluating Clay was like, great that you're landing these logos.
How many stick around?
How many double their spend with you?
And the metrics that I got, I think I can share.
They were like, we haven't turned 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 want to go do more with you?
The hard 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 like actually like personal wealth accumulation, especially in the short term, if you can go from one to 200 in a year, like some of the AI companies with shitter NDR and shitter churn metrics, if you can carry that out for two to three years on a comp basis from stock, you'll have secondary opportunities to sell 10, 20, 30 million dollars worth.
Maybe.
And building a really secure business that grows 3, 4X, which, by the way, is amazing.
Which is great, which is incredible.
Yeah, but it's just like not that.
You're like, it's amazing, but it's actually amazing for 2011, right?
People get caught up on 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 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., right, a high-flying, fast-growing AI startup, they might give you, let's say they give you a million dollars of stock and you're like, holy shit, I'm rich.
And by the way, this is growing so fast, it's going to be $20 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 going to do tender offers and then never does a tender offer.
And so now you're sitting on however much stock you have that is probably life changing for you.
So 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 going to provide liquidity 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 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, comp?
We had a guest on the show that said before, you know, 20x quota.
How would you advise me?
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 salesperson, I saw that and I said, huh, okay.
And like, you know, there's a lot of companies that have done that in the early days, like Stripe did that in the early days.
In other words, no bonuses.
No bonus.
No cash compensation tied to any performance in a structured way.
Yeah, yeah.
OpenAI did this too.
I saw that and I said...
Incredible that it's gotten you this far.
Let's figure out how you reward and attract and retain the right talent.
I'll give an example.
We just hired a GTME, our version of a rep.
You 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-eyed jet from JFK, got breakfast with her, and the conversation was, how do we go make a million dollars here?
How do I W-2 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 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 two salespeople?
Here's what worked at Heap.
And I actually really- I'm pushy.
Do you agree with me?
It's fucking stupid not to have a title performance.
I do, just because, like, I'm an athlete, right?
I also think it's arrogant to be like, oh, don't worry, you're paid in the equity, too, so, like, just good luck.
We'll go back to your point.
If there's no tenders, we're like, thanks, but that doesn't pay the mortgage.
I think what it does is it just allows people to just, like, hide.
And the way I actually say this to people when they're like, 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 overperform 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 overperform, I want to make more money.
And like, you know, that's 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 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 OK in certain areas.
But like, I'll tell you the thing that Todd.
Todd, who I just hired at Clay, 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 had to pay back our base salary.
So like every month it was like, I don't know, five grand.
So the first five grand of revenue was a wash.
Beyond that, every dollar that we closed, we got 25%.
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 to make 25% of every single deal that I closed.
It aligned our incentives with the company's incentives very, very directly.
And we just sprinted at it.
And then we compete with each other.
We'd be like, who can do the first $100,000 deal?
Oh, I got the biggest deal now.
I got the biggest deal.
And it was like everybody was celebrating.
Everybody was making.
good, you know, good money.
And that was it.
It was simple to administer, very direct.
When we built our comp plan at Clay, you know, I feel like it's really easy to make it really complicated.
I'm like, oh, 20% of your, 20% of your variable 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 can I ask, what do you have then?
So you have a quota, obviously.
What is the quota?
Our quota to OT ratio is like, I think it's like seven and a half.
Quite good.
Quite high.
I was always brought up in the enterprise world by three to four X was kind of where you are.
Well, I think below four X, it's like, yikes, right?
I've always taught four to six.
Four is kind of shit.
Six is like, wow, you're doing great.
I think in the AI era, you have 20 X, your base salary is your quota.
That's pretty wild.
Punchy.
Right?
It's punchy.
Punchy.
But I hit the ground running for that one.
It's punchy, but like...
You've had the first 12 minutes now, Sal!
Yeah, in the AI era, I feel like, you know, we're seeing somewhere like 6 to 10, depending on...
the business, the types of deals, size of deals, who you're selling to, but we're at 7.5x quota to OT ratio today.
If it doesn't make sense, we're going to 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.
Sorry, this is where I mentioned I'm not too fast, which is why I'm a venture capitalist.
So I need to hit 6 to 8x my salary.
Yeah.
And then what happens?
And then I get what?
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% of your number?
I mean, 6, 8x is quite a lot.
And only then I get it?
Jesus, fuck.
So what I'm saying, what I'm hearing is you don't want to come work for me?
No.
This 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?
Well, so 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 shaggy.
It's exhausting.
Look, you have your OT, and we pay like, you know, pretty competitively, I would say, above and beyond your quota.
And this is actually the argument that we're actually having right now.
I spent probably two hours in the last two days with my RevOps leader, Varun, Kareem, our finance leader, our strategic finance team on what are the accelerators?
Because my perspective is if you're overachieving, 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.
If you're hitting 150% of that, we come back to like, 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 100 reps, right?
60% of them are hitting their number.
Great.
Just hitting.
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%, 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 rule of thumb that I like.
Our strategic finance guy was like, oh, it's 50 over 100 at my last.
Great, whatever.
You agree on some percentage of your team is over 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.
How do you know when you are setting the wrong goals versus have a shit team?
Because two different people could go, oh, we've got too high expectations, or it could be you're just hiring shit people.
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, they 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 were 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, OK, well, thanks.
But like, that's how you do it, right?
You have, let's say you have 100 reps.
There's going to 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.
Well, I'm an ambassador as well.
And I was in Vienna the other day to try and lead a series A.
Sounds fancy.
Thank you.
I lead a very glamorous life, not just short shorts.
But we went into this office and there was a sales leaderboard and it had, you know, whatever, eight wraps, kind of a series A early stitch company, so eight wraps.
And me and my partner in the firm were like.
oh yeah, we like this.
Like we felt the competition and we felt the like, they are looking at their numbers and they are on every new deal, every pipe.
That's coming to our sales floor.
We've hired non-traditional salespeople.
So you kind of have to like incrementally introduce some of these concepts.
But like, you better believe we're going 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 to be at the top on the revenue dashboard.
100%.
Is there anything that we can do to inspire that competitiveness within sales teams to make them incentivized, encouraged, to kind of fight between them?
Hunger Games of sales.
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 deal at Heap and then he was like, awesome.
fuck, 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, right?
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 want to go beat you.
And I think even at DBT, right, which is like an 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 a weird dance to do.
Once you get big enough, 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 need to go get Siemens or Allianz.
We need to go get a bigger deal there.
And you kind of just cut, you pit people against each other 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 Americas team, I'd say, hey, 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 kind of like, you put a little chip on people's shoulder, but in a fun way.
And totally get it, just kind of.
demoralize them in a really fun way.
It's not demoralizing if the company's growing 3 to 4x, which you've just told me is now shit.
You're becoming inherently less important, but feel good about it.
So we have 6 to 8x quota.
And then what happens?
So I'm your rap.
Say I did join.
Did you join?
No.
Sounds like you have some reservations.
You're on a high base.
You don't need to whack it up.
But 6 to 8x, what happens then with the accelerators?
So like if I pay you 10 cents on the dollar before, it should jump.
But for every new deal at Clay now, do I get 25%?
It doesn't jump up that high.
You know what?
I know, very disappointing.
Why did it at Heap and not at Clay?
I mean, we did it at Heap because we were the first two reps.
And they were like, just go fucking close as much.
So you can't have that higher with scale.
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 we charge for a credit of data.
And actually, our economics are very, very good.
Our head of finances.
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 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, and then on top of that, you get accelerators, right?
All that Heap did was just jump straight to the accelerators and say, you have an artificially low base.
Now go work your ass off.
One thing that you said there are kind of about not great margins with AI companies, and a lot of them don't have great margins because they also give a lot upfront.
That's right.
And inference is their kind of sales and marketing costs 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 like a PLG motion, right?
And if you have usage, 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 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 a PLG motion for your company, your AI widget, and then 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 them.
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 going 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.
Trump would be proud.
But you think about going and 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 going to win that.
How do you build internal champions within businesses?
What's your biggest lesson?
Okay, so if you actually ask anybody on my team, I hope that they don't listen to this because they're going to groan.
I will...
oftentimes just say, okay, do you have a champion?
And they're like, I have a, yeah, this 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 doing this?
The personal win is they personally gain from your tool benefiting their company.
Yeah.
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 I kind of want to get into venture and investing and advising companies on AI.
And I'm leveraging what I'm doing with clay to show that I'm that person.
And I'm like, that's an incredible personal win.
At DBT, you would talk to folks and you'd be like, yo, why do you care so much about this?
This is just data transformation.
And 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 shit.
And then when I leave this company, I can go to another company and be the data guy and come in, hire a salary, get more equity, whatever.
If you focus on that, if you can get to that, you probably have a champion.
And, like, they're probably going to go to war for you.
And they have to have the other two 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.
That never happens.
That never happens.
But Mitsubishi, they 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 over the line.
Here's a big one.
Oh, this actually happened to one of my reps.
Oh, you know, I didn't know how many approvers needed to sign this big expansion.
The signer is actually the CEO of this big company, is on his island in Hawaii.
Fuck.
And I'm like, okay, well, 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, right?
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 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 one of the GTMEs out here and she was like, oh, well, yeah, yeah, he's a bad champion.
I'm like, whoa, whoa, whoa, hold on here.
And you kind of have to be meticulous and like kind of an asshole about when people say like, qualify champion.
I'm like, no, no, no, it's binary, right?
If you're a bad champion, is it really your champion?
You're either a champion or you're not a champion.
Let's be really clear about it.
And if you say they're a champion, what have you seen with your two eyes?
It 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 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 that they were your champion, and you probably didn't do the best job.
When we sit down and we do postmortems and we do collaborative forecasting on what we've done and what we've got ahead of us, how often do we do that?
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, okay, 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 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 of deals with reps and it's a lot of fun.
What are the biggest mistakes sales leaders make in forecasting?
At the front line, 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 would love to work with John Dalton for the rest of my life.
He also lives in Santa Barbara.
He's very chill.
He has a very, very nice life.
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, 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 company?
And she's like, ah, 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 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.
We get that big logo.
And 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 the maintenance of that relationship with the rep, who's a hunter, versus like handing off to cushy cushy nice CS.
And then one of your competitors, hunters, 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 CS who's now like, oh, softly, softly.
And the hunter's going.
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 12 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 helps protect the unit economics because you know that you want to go and expand that.
But two, you sell a shitty deal?
You're going to renew that shitty deal and you're probably going to take some churn of 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 it's because they're competing over workflows in the account.
It's the same for us.
You said about like, oh, the discount, then you've got 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 at all.
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 like straight up called us on it.
They were like, is my money not green on April 1st?
And I was like, fair play.
I think everybody knows at this point that if I'm giving you a discount on, you know, 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 like when we buy software, right?
Like, I don't know, the rep was like, hey, I can only do this if you do this by next Friday.
And it's like, actually, I don't give a shit about your timeline.
I need this software today.
So like, yeah, I'm going to move fast.
You know, we bought like 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 going to try to get this deal done before next Friday.
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 skipped a step.
Let's go back and let's figure it out.
You said you buy software.
I am friends with Jason Lemkin from Sasta, who's like, I just got rid of a lot of my team, including a lot of my sales team.
And we have AISDRs, we have Artisan, we have Qualified, we have Monaco now.
Like, fuck, I don't need them.
I'm doing more, I'm doing better with less.
How does the world change with AISDRs?
Are SDRs dead?
Is Outbound dead?
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 $40 million of pipeline because you have a, I don't know, $10 or $15 million revenue target, but like...
When you get into having to build a quarter billion dollars of pipeline, it's actually probably a little bit more efficient to just put some hungry, scrappy 24-year-old on the field, pay them a certain amount of money and say, go run at these accounts.
That's the first thing.
The second thing is like, hey, you don't have an SDR team.
Who the hell are you going to promote into your closing roles?
It's completely 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 i'm out here we have uh 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 multi-threading 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 just the same message coming from a different mouth.
Totally changes everything.
Yeah.
It gets a completely different response.
And so I encourage people to think about it.
One of the GTMEs that I was talking to out here in London.
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?
You get a Sequoia partner to LinkedIn message a CEO.
100%.
There's an increased chance of that response.
Yes.
100%.
One of our portfolio companies, the CRO, comes in every month and gives me like a top 10 target.
So I just go with them to the CEOs on LinkedIn.
I have a blue check mark and lots of followers on LinkedIn.
Very important.
Very important.
Challenge shit on LinkedIn.
Nine out of ten respond.
Yeah.
They're like one out of ten.
Totally different.
I completely agree with you.
So yes, 100%.
You said about, 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's like the best form of marketing is employee-led marketing.
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.
If you work at Clay and you want 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.
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 are like, ooh, that 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, you know, we talked a lot about, like, the cultural things that we do that are fun, right?
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.
Like, that's kind of modern marketing.
You said AI doesn't change SDRs.
It doesn't change Outbound.
What does it change?
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 this is like my thesis with the ClayDR team is like, let's say 2018, an SDR can book in a given month, say they're booking 15 meetings, right?
If I can arm that rep with Clay and a clawed 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, Yes, please.
Thank you.
Okay.
Now I want to 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 going to cut our SDR team in half.
I'm like, hmm, okay.
That's an interesting move, right?
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 go multiply that into infinity and take all the space all the oxygen out of these accounts but 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 off to an ae if you think you can replace it entirely and just hand off to an fd you can get an infinity with one tool 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 AD?
Right now, none.
Right?
Yeah.
So it's like, okay, 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 the AI tool and brought it in, but here's two tools that we use pretty aggressively.
Everybody uses Level.
Everybody uses Claude, right?
I was talking last night with a bunch 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?
It's very personal.
So Granada, 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 will give them money.
Chris is a friend of mine and he basically came to me and he was like, AI and notes.
It's going to be a thing.
I don't have any clue how, what, where, when, but that's the thing.
I've been in Rome Research.
I've been in all the other student notes.
Do 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, and I just sent it to Varun and my talent partner.
And it's very cut and dry.
There's no emotion in the Granola notes.
And Varun was like, this is this a positive like was this a positive reference and i was like yes it was glowing and i looked back at the ganola notes and it was like just objective like yes stay you know stacy helped me in this deal like blah blah and i was like okay got it i'll figure out it i'll figure out a different process so like they got some things to work and then whisper flow to me i never had the chance to invest in them but i i loved them i used them the whole freaking time i never type anymore like never type 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.
So, hey, Whisperflow, if you could fix that for me, that would be really great.
So annoying.
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.
what am I going to say?
If I can just press a button and say, like that's how 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-da-da-da.
And it does the whole thing for me and I just hyperlink.
Yeah, and you can add it a little bit if you're like, I didn't want to say like, yeah, yeah, I have that too.
I find it better for hard emails, ironically, where like, you know, it's difficult to know what to type.
It's easier to know what to say.
To say, yeah.
Yeah.
So I don't know if you know Bill Bench over at Battery.
I remember interviewing him when he was at Pando.
Oh, yeah.
I have a ton of respect for him.
And like, if you've been an operator that long, like, God, you've got some thick skin.
But he said the other day, he was like, no one's going to type anymore.
Like, 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.
Like, I don't really type that much anymore.
I completely agree.
But you haven't used the AI SDR tools to boost productivity.
You're not pushing them.
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 go.
Don't be a dick.
It's not that intuitive.
It's not that easy.
Well, it's not that easy.
I've tried.
Varun and Bruno keep on trying to get me to do stuff.
Okay.
And it's a bit fucking complex.
I don't know where to start.
Well, so actually it's...
It's a bit of a blank page 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?
Whisperflow is like, just talk.
I can't just like verbal diarrhea clay.
You can now.
Well, you can't verbal, you can type diarrhea.
Maybe if you can use Whisperflow into Sculptor, which is like our kind 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 was like when I was...
I guess interviewing or talking to Varun about joining Clay, there were a bunch of things that I was like, hey, and what about this?
Because like my wife uses Clay or like, you know, 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 not Claudified?
You could probably use Claude to say, hey, give me the top 50 oil companies in Austin, right?
Find the CEOs of all of them.
Get me their email for each of them.
Actually, Open Air will fuck you on that one straight away.
They're like, no, we don't provide emails.
Well, that was fucking useful.
But think about it.
One 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?
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 get 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, so.
I totally get that.
Listen, I could talk to you all day.
I want to move to a quick fire round.
So I say a short statement.
You give me your immediate thoughts.
That sound okay?
Oh, okay.
Yeah, we'll do our best.
Okay, so what's the worst hiring mistake sales leaders make?
Focusing on the last company that they were at and if it was a playbook company or not.
So, 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 Rubric.
And actually, I was texting with a friend last night.
A lot of people are now moving from rubric to cursor.
Rubric, very playbook company.
Cursor, AI first company.
And I have a ton of respect for those guys and all the playbook folks.
And I think what they've done and what they've taught the craft of sales is really, really valuable.
It's going to 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 going to be thrown out.
I 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.
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 hundred of the same kind of person versus people who are going to actually push the envelope.
What have you changed your mind on in the last 12 months?
12 months ago, I actively resisted using AI.
I was like, I think it's going to make people dumber.
I think that 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, now I work at an AI company, so maybe I'm a hypocrite.
But basically, I went from saying...
Fuck that.
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?
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?
Do sales teams have to be in person?
In person with customers or in person in an office?
In an office.
I'm a five-day-a-weeker.
I show up to the office five days a week.
I'm here in London for these four days.
Tomorrow, I'm going to go to the office on Friday.
I think that you get so much more when you're working in person with your team.
I get FOMO when I'm not in the office.
Are you not pissed when you go in and other people aren't in?
Friday is the new weekend now, especially in Europe.
Friday is work from home Friday.
Fuck off.
It's not work from home Friday.
I would never let work from home Friday or Monday.
It's basically an extended weekend.
Look, I don't track attendance.
And 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.
feel like they don't want to be sellers.
So 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, hey, we're not just making 150 cold calls a day and indiscriminately trying to sling our product.
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 a lot of us out here.
When is the right time to verticalize sales teams?
You said about critically thinking about a business.
That's a good question.
Thank you.
Ten years of vision.
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 to like, you know, everybody has a finance vertical or they hire someone to Detroit to sell to the big auto companies, right?
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, that's dead.
Like the relationship type of sale of like, well, I know all these people, I have this Rolo.
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.
What ACV is justified for a sales rep?
So you see lots of PLG tools where they're super cheap and you're like, well, they could expand, but they could not.
Like, what's the...
I mean...
i'm not a math major right so like there's there's a math equation in there that i 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 our 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 and justify it right i you know you talk to like hubspot and they're at the size where like yeah they've got reps that are working like nine thousand dollar deals right they're at a different scale and they can do it light touch with a lot at the same time yeah right and they're like our average you know we do a three call close and it's nine thousand dollars 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 What's your favorite win story of a deal?
That's a good question.
Thank you.
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 an EB.
She was the chief digital officer, chief data officer, and she just fucking got it.
Man, she was maybe a little bit earlier in career for a C-level role.
She was super innovative.
She would come to us and she'd be like, yo, I'm checking out these other tools.
What do you guys think?
How do they play?
Does this story make sense?
So it was almost like working with a friend that was 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 going to sell to my classification, poor rich people, people who had between $10 million and $50 million of net worth.
And they were going to launch 10 of these products and they were expecting each of those products to generate $100 million for them.
And I was like, wow, like you've thought about, like 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, it was a fun team.
I actually, my favorite deals.
are not the biggest deals.
It's the deals where I'm working on one right now with one of the GTMEs on my team, and I show up to the calls, and we have our plan.
We know what we're trying to do.
We're like, hey, we need to drive these steps.
But the people on the other end of the phone are...
Two women who have their shit together very clearly 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?
And I'm like, you're thinking about it exactly the right way, Christy.
You're doing great.
What's the biggest deal you've ever closed?
Me personally?
It was $1.1 million for three years.
So it was like 3.3 TCV with a large financial services company.
That's a good day.
It'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.
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.
Mark Andreessen would call that retard massing.
Let life do its thing.
And you're like, you know what?
It did its thing.
Yeah, 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.
But before we leave you today, a quick shout out to a company I've been genuinely blown away by and have been tracking closely, ROX.
I've been watching this team closely and the speed they're operating at and the level of applied AI talent they've assembled, it's honestly remarkable.
ROX is pioneering revenue agents for the global 2000, plugged into your data warehouse and CRM and delivering board level ROI in just 90 days.
These sales and revenue agents handle the end-to-end sales process for large enterprises from research, prep, to deal risk, outreach, and opportunity management.
So sellers spend more time with customers and less time in tools.
This isn't another productivity app.
Christ, we've all had enough of those.
Rocks gives reps a single interface on top of their GTM stack, powered by a knowledge graph across your internal and external data.
So if you want to boost AE productivity, increase revenue per rep, and consolidate your stack, try Rocks at rocks.com slash sign up.
while rocks keeps your revenue team aligned granola keeps your calls captured and actionable you're in back-to-back meetings all day you're trying to stay present but you're also worried you'll forget the decision the action item the important next step that's where granola comes in granola is an ai-powered notepad for meetings you jot down rough notes like you always do and in the background granola transcribes and turns them into really clear useful notes when the meeting ends no bots joining your cool no distractions just a clean notepad that helps you focus during or after the call you can chat with your notes ask granola to pull out action items help you negotiate write a follow-up email even or coach you using recipes which are pre-made prompts it's actually the same technology we use to create our podcast notes once you try it on a first meeting it's really hard to go back head to granola.ai forward slash 20vc that's granola.ai forward slash 20vc and get three months with code 20VC, that's 20VC.
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