Skip to content
The Twenty Minute VCThe Twenty Minute VC

Inside Clay's Sales Playbook | Becca Lindquist

Becca Lindquist is Head of Sales at Clay, one of the fastest-growing AI companies to reach $100M+ ARR. She previously helped scale dbt Labs into a category-defining data platform, building and leading high-performing sales teams. Before that, she was an early sales leader at Heap, where she played a key role in scaling the GTM motion. ----------------------------------------------- Timestamps: 00:00 Intro 01:09 Should You Leave Your SaaS Job for an AI Company? 03:48 How to Read a LinkedIn Profile: Red Flags & Green Flags 10:03 Domain Expertise vs High Slope: Which Hire Wins? 11:53 How to Spot a Bad Hire Before You Make It 15:30 How Fast Do You Know If a New Rep Is Going to Work Out? 17:03 What Good Sales Bootcamp Looks Like at an Early-Stage Company 18:14 What to Look for When Hiring Your First Sales Reps 21:03 How to Pick the Right AI Company to Join 22:55 The NRR Question: Is It Still the Most Important Metric? 26:30 How Clay Finally Introduced Variable Sales Compensation 39:10 AI in Sales: What's Real vs What's Hype Right Now 40:37 How Your Sales Motion Changes With a PLG Product 42:37 How to Build Real Internal Champions 47:58 The Biggest Mistake Frontline Sales Leaders Make 53:05 Is Outbound Dead? 57:24 What AI Actually Changes in Sales (vs What It Doesn't) 59:08 Best AI Tools Becca Uses 01:05:01 Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Clay on X: https://twitter.com/clay Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #sales

Becca LindquistguestHarry Stebbingshost
May 2, 20261h 14mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 1:09

    Intro

    1. BL

      How do you read a LinkedIn profile?

    2. HS

      Oh, wow.

    3. BL

      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.

    4. HS

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

    5. BL

      Our quota to OT ratio is, like, seven and a half. It should be heavily weighted towards over performance. If I'm giving you a big quota and you're hitting 110% of that, I want you to be making good money.

    6. HS

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

    7. BL

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

    8. HS

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

    9. BL

      Hire two at a time because you hire one, you're like, "Is it good? Is it not good? I don't know." You hire two, it's pretty clear. Outbound will never be dead.

    10. HS

      Ready to go? [upbeat music] Becca, it is so good to have you on the 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.

    11. BL

      Thanks for having

  2. 1:09 – 3:48

    Should You Leave Your SaaS Job for an AI Company?

    1. BL

      me. It's fun.

    2. HS

      Now, I think a lot of sales leaders and salespeople are looking at themselves, they're 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-

    3. BL

      [laughs]

    4. HS

      ... 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?

    5. BL

      So I have a lot of these types of conversations, both with, like, peers and, and with, uh, folks that are, uh, having this, like, kind of evaluation, and I think there's, 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, and, like, the, the phrase that I use to describe how they might feel is like, "Hey, do you feel like you're kind of, like, rotting?" Right? Like, you're, you're not, you're not learning a ton more. The, the, the learning curve is flattened for you. You're not in an AI space, which, like, I think is, like, the next, uh, the next phase of things to learn. And actually, almost every time they're like, "Yeah, that's exactly how I feel." And I'm like, "Okay, let's, let's fix that then," because that, it... Once you stop learning, like, you actually as, as a person, I think, start to settle, and then it's just a, um, like, a process of settling all the way down to the bottom.

    6. HS

      So what do you do when you feel, as a sales rep or leader-

    7. BL

      Yeah

    8. HS

      ... that you are rotting? What, what do you do then?

    9. BL

      You gotta go f- You gotta go find something else, right?

    10. HS

      You can't reinvigorate it?

    11. BL

      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's pretty big. There's a lot of structure. There's a lot of process. Like, there's, there's not much more for you to, like, innovate meaningfully. I mean, maybe you could, um, I don't know, maybe you could go run the company's, like, VC fund or something, right?

    12. HS

      [laughs]

    13. BL

      Like, but, but, 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, like, you're gonna learn way more. The surface area of, of what you can actually go and impact is much, much higher.

    14. HS

      Hmm.

    15. BL

      And I think that's what those types of people are excited about, right? Like, if you've been at Salesforce for 12, 13, 14 years, like, you've probably had an incredible run. You probably really enjoy that, and you're probably gonna stay there. But, like, most people are at companies for, like, four or five years, right?

    16. HS

      Dead 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 are happy just in this kind of melee of mediocrity for 12, 13, 14 years?" Is that a bad read?

  3. 3:48 – 10:03

    How to Read a LinkedIn Profile: Red Flags & Green Flags

    1. BL

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

    2. HS

      Oh, wow. I love this.

    3. BL

      Right? And I... We just pulled up people's LinkedIns. We pulled up yours. It was actually really weird. We're like, "Don't hire this guy." No, I'm kidding. [laughs]

    4. HS

      [laughs] Terrible. Look at that picture. Egotistical, arrogant. Why would I hire-

    5. BL

      Yeah.

    6. HS

      He's a team player.

    7. BL

      Terrible rep.

    8. HS

      Next. [laughs]

    9. BL

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

    10. HS

      But what is that amount of time? Because I also hate the bouncer, and the, the, the biggest red flag for me is 13 months here-

    11. BL

      Yeah, yeah, yeah, yeah

    12. HS

      ... 15 months here.

    13. BL

      That's, that, that, the, there's, there's a lower bound too, and, like, I think, I think it's two years, right? Like-

    14. HS

      I, I was thinking four to five years is, like, optimal.

    15. BL

      Yeah. I mean, that's... I, I've spent the last decade at two companies.

    16. HS

      Yeah.

    17. BL

      Right? And, like, I've built something. I've learned a ton, and when that learning curve starts to cap off, like, okay, you start to think about what's next and what's new. I think it's probably, like, seven years. Six to seven years. After that, if you've been in a company for eight, nine, 10 years, it's like the company's kind of built around you probably.

    18. HS

      Yeah.

    19. BL

      And you, you've built so much of it to, like, uh... I don't know the best way to describe it. It's, like, maybe, like, putting on someone else's shoes, right? Now, now I'm giving you, you're giving me your shoes. Now, like, I gotta, like, I don't know, redo the laces, and the insole's all s- you know, screwed up. Like, I think it's really tough for someone who's been at a company that long to, like, adjust. And, and prove me wrong, right? Like, I, I have a friend who was at, 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?

    20. HS

      Yeah.

    21. BL

      Where it's like-

    22. HS

      Oh my gosh, yeah

    23. BL

      ... 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."

    24. HS

      [laughs]

    25. BL

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

    26. HS

      [laughs]

    27. BL

      [laughs] Don't open that up.

    28. HS

      That is so denigrative. I love that. That's so funny. Yeah, yeah. Um, training and recruiting. Take me to that day. On, on the LinkedIn specifically, is there anything else, like, we watch out for? Don't laugh, one of my big red flags is someone who has, like, a picture of them speaking at an event.

    29. BL

      Okay. [laughs]

    30. HS

      It just tells me that they have great self-importance.

  4. 10:03 – 11:53

    Domain Expertise vs High Slope: Which Hire Wins?

    1. BL

      I mean, like, so think about everybody, think about everybody that we've hired at Clay, right? Like, we've hired kind of non-traditional sellers. And, 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, right? So I think about someone like, um, [clears throat] I had a, I had a rep, uh, at dbt who worked for, for me. Um, he spent six years at Bloomberg, right? And we hired him in as a commercial rep. It may be... I can't remember if it was six years. Yeah, whatever. He came from 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. Like, 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 and sat down with him. I was like, "Hey, what do you wanna work on together?" And he was like, "I'm really screwing up in the sales cycle. Here. Can we work on that?" And we, like, did it, and it was like a quarter later, he, he was, like, doing it in every single deal. And that, like, just gave me the confidence to say, like, "I'm gonna invest in this person." Came to me, like, a year and a half later and was like, "Put me into this role. I'm gonna, I can do it." And I was like, "Okay, let's go do it together." And, like, I think he was top three reps worldwide at dbt. So, like, that's, that's actually what I look for outside of, like, you know, like, domain knowledge is helpful for certain areas and certain profiles or certain levels. So, like, John Dalton, who I called out, like, I would hire... I, I'd hire John Dalton anywhere, but I'd hire him as, like, the first rep if I was in the data space. Like, that's the kind of person you need early on with, like, a little bit of ex- 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, you know, 100, domain expertise becomes a little bit less important, but the high slope is, is the most important

  5. 11:53 – 15:30

    How to Spot a Bad Hire Before You Make It

    1. BL

      thing.

    2. HS

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

    3. BL

      You know what? We actually, uh, I incorporate this into, um, my hiring flow for leaders. I give them feedback, or I have someone else give them feedback. Ideally the recruiter. And you know why?

    4. HS

      Why?

    5. BL

      Because if I give them feedback and they push back or they're, you know, they're kind of a dick about it, I'm like, "Oop-Okay. Probably not gonna work, right?

    6. HS

      So this is feedback in the job interview?

    7. BL

      Yeah. I'll, I'll say, like, I'll give an example. I hired, 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, gave me s- like some feedback. So I just called him and I was like, "Hey, how, how do you think it went?" And like, you know, "Okay, great, great, great." "Hey, this is something that, like, this is something that I got. Like, this was part of the feedback that I got. What do you think about that?" And you just listen, and it tells you everything that you need to know about what it's gonna be like to work with that person, right? If they're like, "Oh, well, like, oh, uh, he, he didn't really say it that..." "Oh, interesting. Okay." But if they're like, "Okay, yeah, that's fair. How do I go, how do I go and overcome that?" And they're like, "Yo, what do I do?" That's actually very interesting, especially in, in a company like Clay, where we're like, I don't know, building something new. There's a lot of, like, open white space, right? If someone's really defensive, that's actually the biggest red flag, and I... We need to incorporate it into the, into the rep interview. Um, but, like, that's... I, I made a hire one time [clears throat] and, and ever since I've kind of just said, "Okay, I'm gonna give you the feedback and let's see how you react." And actually, it's even better if the recruiter gives them the feedback. It's sort of like when you take someone to a, you know, you take, take your girlfriend or your wife to a restaurant, and you see how they treat, you know, the hostess and the waiter.

    8. HS

      One of the biggest signs I look for.

    9. BL

      Right?

    10. HS

      If it's bad, I'm out.

    11. BL

      Right? Yeah.

    12. HS

      100%.

    13. BL

      It's the same, 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, I'm out.

    14. HS

      Instead, mine just beats me. But 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 s- salary, they tend to be good-

    15. BL

      Yeah

    16. HS

      ... and know their worth.

    17. BL

      Yeah.

    18. HS

      So really all my mis-hires are when, "I'm not happy being a EA. I wanna be a chief of staff."

    19. BL

      Ah.

    20. HS

      But you're, you're an EA, right?

    21. BL

      I agree.

    22. HS

      You, uh, you're happy with the salary, so you're not agreeing to that, but it's actually that. Always a mistake.

    23. BL

      Oh, yeah.

    24. HS

      When, "Oh, I don't care about title, but I'm worth more."

    25. BL

      Yeah.

    26. HS

      That's when I make mistakes.

    27. BL

      That's, that's actually, that's... If you think about, so, like, we talked about Todd, right?

    28. HS

      Yeah.

    29. BL

      Same, same, me and Todd, we agree on that. Like, I was like, "I actually don't really care what my title is. I do care how much you pay me. I do care how much equity I have, and I do care about scope. But, like, fuck, you can call me Go-To-Market like every other AI company."

    30. HS

      Yeah.

  6. 15:30 – 17:03

    How Fast Do You Know If a New Rep Is Going to Work Out?

    1. HS

      How fast do you know when someone's shit that you hire?

    2. BL

      If it's an IC, and actually I listened to one of your pod- uh, podcasts you were doing with someone else, and, uh, you were talking about this. How do you know a big enterprise rep, big deals person, how do you know? Like, they have a nine-month ramp. How, how the fuck are you gonna know in month three if they're good or not, right? Um, you know for an IC, like, within probably three weeks, right?

    3. HS

      What are those signs?

    4. BL

      The signs are, uh, can they think critically about someone else's business? So, like, if, if... And, and that would be, like, the sign of a mis-hire, right? You put a, 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 two-week boot camp. Here's your 100 accounts. How do you stack rank them?" And they c- just completely whiff it, or they're like, "I, I don't know," right? Like, ooh, that's a big red flag. Um, the second thing is, like, what are their activity metrics, right? Like, okay, you just exited boot camp. First I wanna know how they did in boot camp. Like, were they engaged? Were they, were they failing alone, right? Were they asking questions? Were they leaning on other people? Um, once a- once you get out of boot camp, it's like, okay, uh, are you thinking critic- critically about your prospects, their business, how we can help them? Are you fucking hitting send? Are you doing the thing, right? Are you picking up the phone? Are you hitting send? If you're not, you're not generating pipeline. It means you're not gonna be successful, right? So, like, those are the early flags of, like, hm, this person's not gonna work out.

    5. HS

      Totally get you. You said that boot camp quite a few times.

    6. BL

      Yeah, yeah.

    7. HS

      I, I presume we're not talking about Pilates, which is what my mother will think about.

    8. BL

      [laughs] Yeah, I take my whole team down to Barry's Bootcamp every week.

    9. HS

      Yeah. [laughs] It's like, "Whoa."

    10. BL

      Yeah.

    11. HS

      Peter Boyle will be pleased. Um,

  7. 17:03 – 18:14

    What Good Sales Bootcamp Looks Like at an Early-Stage Company

    1. HS

      no, like, a lot of founders really struggle with, especially early founders, like-

    2. BL

      Yeah

    3. HS

      ... "How the fuck do I train my reps?"

    4. BL

      Ooh.

    5. HS

      "I've, I've never run a sales org. What, what is boot camp, Becca?"

    6. BL

      So, so, well, that's, that's a little bit later stage thing. Um, when I joined Heap and when I joined cl- uh, dbt, we didn't, we didn't have a boot camp.

    7. HS

      So how should early stage founders train reps?

    8. BL

      So here's, here's what we did at Heap.

    9. HS

      Mm.

    10. BL

      Um, basically Mateen and Ravi, it's like they showed, they did the thing. We rode along, and then that shift started to sh- kind of, like, happen of, like, okay, now we run the call, and maybe you're on a few. Now you have Gong, so you can actually send the people that you hired all of your Gong calls before. Like, that's... All the founders that I work with, I tell them, like, "Yo, do you have Gong?" And if they don't, I'm like, "Ooh, red flag. You gotta go, just go get, just buy it," right? Um, and then send whoever you hire all of the calls that you've done because they're gonna... One, they're gonna give you feedback on, like, how to sell, but two, they'll hear how you talk about it, and that's actually the most, 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, right?

    11. HS

      So if I'm a founder hiring today, early stage company, under 10 million

  8. 18:14 – 21:03

    What to Look for When Hiring Your First Sales Reps

    1. HS

      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 is really early stage. Like, what is that profile?

    2. BL

      I keep coming back to, like-Thinking critically about your customers. So like I'll give an example. Maybe you're selling an AI widget.

    3. HS

      Sure.

    4. BL

      Right? Does this person come in and talk about the widget, or do they talk about how, I don't know, uh, JPMC would use it, or the company that they're currently at, how they would use it, and the impact that it has? And like what I, what I mean by impact is like, I'll give an example. [clears throat] Whenever we talk about AI tools, I feel like we talk about like the art of possible, like pie in the sky stuff, and I'm like, "Hey, hey, hey. We're, we're ... 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, it, it automates, 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 do ... 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, is screwed up," or, "We miss our revenue target," or like, "Our rep productivity sucks because of it," right? 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? And like obviously I bias towards having college athletes because they've, they've learned how to work hard. All you gotta do is teach them how to work smart. If you teach them how to work smart, it's really tough to teach someone how to work hard.

    5. HS

      I think they also have the discipline to do the work when no one is watching.

    6. BL

      Yeah, that's-

    7. HS

      Like-

    8. BL

      ... that's true

    9. HS

      ... you're an athlete, and I like to think that I am. Um, like-

    10. BL

      [laughs] Well, you ... I don't know. You show up with those pretty cool M frames.

    11. HS

      Thank you so much. Um, but like most of the time is spent in a gym with no one else in-

    12. BL

      Yeah

    13. HS

      ... at 5:00 AM in the morning, and, [laughs] you know, that black tie dinner where you hopefully look relatively athletic is once every six months-

    14. BL

      [laughs]

    15. HS

      ... where the world might see that you're fit.

    16. BL

      Yeah, that's right.

    17. HS

      But that's it.

    18. BL

      That's right.

    19. HS

      So those six months of shit.

    20. BL

      The posts and things you post on Instagram. Yeah. [laughs]

    21. HS

      Yeah, yeah, yeah, of skipping donut time and skipping everything else.

    22. BL

      Yeah.

    23. HS

      Uh, I totally get you. On the flip side of that, what you look for, we, 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.

    24. BL

      I know.

    25. HS

      And they all have shiny VCs, and they all have people-

    26. BL

      Uh-huh

    27. HS

      ... who are pronouncing themselves to be replacing work for every large profession.

    28. BL

      Sure.

    29. HS

      What would you advise those sales reps who feel like they've plateaued, rotting, that's a good-

    30. BL

      If they're rotting, yeah

  9. 21:03 – 22:55

    How to Pick the Right AI Company to Join

    1. HS

      which one should I choose? [laughs]

    2. BL

      That's ... Honestly, it's, it's really tough, and like I obviously like, uh, I, I hadn't intended to leave dbt, if I'm, if I'm honest. Like I was like, "I'm gonna finish out the fiscal year, and then maybe I'll start to think about what's next." Um, and I, I met Varun, and you know Varun.

    3. HS

      Yeah.

    4. BL

      We went for multiple walks around ... He lives around the corner from me in Brooklyn. And so I, I, I feel like I got a little bit of the cheat code because I, I do think that Clay is like the most compelling company on the planet right now. And like when you think about AI companies, a lot of people have ... We, we just hired a RevOps guy. He's fantastic. He has this phrase. He's like, "Everybody has the Claude spookies." And I'm like, "That's a really good way to describe it." The, the-

    5. HS

      That's a cool phrase

    6. BL

      ... feeling of like, well, why wouldn't Claude just do this? Is Claude gonna overtake this market? Is Claude gonna put you out of business, right? And it's like there ... it's ... there's a lot of companies out there that I look at it, and I'm like, "Hmm, I got the Cl- I ... Yeah, I think that that could be a thing for you." And so like, uh, the real answer is I don't, I don't really know, but I think about is there something that's not just AI that's defensible, right? Like Clay has this data marketplace. It's really ... It's tough to build that. Like you could go, 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 [laughs] just buying software to do that for you. And so like I would look for some sort of other defensibility outside of just we're automating this, or like, you know, we're, we're gonna automate this profession away or like a workflow, and that's a really tough thing to find. Like there's not ... Like I can't even think of a company that I would shout out that's doing that, right?

    7. HS

      I totally get that. I would say like just look for a company with unwavering product market fit.

    8. BL

      Yeah.

    9. HS

      It's pretty hard to sell shit no one wants.

    10. BL

      That's, that is 100% right.

    11. HS

      And it's pretty easy to sell shit that everyone

  10. 22:55 – 26:30

    The NRR Question: Is It Still the Most Important Metric?

    1. HS

      wants.

    2. BL

      Yeah. Yeah.

    3. HS

      Is it?

    4. BL

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

    5. HS

      Is it easy?

    6. BL

      Uh, it's ... It is easy in the beginning, right? Because you could grow as a company 1000% just by, you know, just by doing the thing.

    7. HS

      Mm-hmm.

    8. BL

      Like, you know, having a, a moderate execution on, on your, on your sales process and, and if you have a really great product, it's gonna fly off the shelves, right? But as you grow, it becomes very challenging to grow 1000% year over year-

    9. HS

      Sure

    10. BL

      ... 250% year over year, right? So like a lot of what I focused on when I was evaluating Clay was like, great that you're landing these, these logos. How many stick around? How many, how many double their spend with you? And like the metrics that I got, I, I think I can share. Um, like they were like, "We haven't churned a customer. Our NDR is close to 200%." Like those are the types of things if you're talking to an AI company, that's a ... 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 wanna go do more with you?

    11. HS

      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 1 to 200 in a year-

    12. BL

      Yeah

    13. HS

      ... like some of the AI companies-

    14. BL

      Uh-huh

    15. HS

      ... with shitter NDR and-

    16. BL

      Yeah, yeah

    17. HS

      ... shitter churn metrics.

    18. BL

      That's fair.

    19. HS

      If you can carry that out for two to three yearsOn a comp basis from stock-

    20. BL

      Yeah

    21. HS

      ... you'll have secondary opportunities to sell 10, 20, $30 million worth.

    22. BL

      Maybe. Maybe, right? I- that's ... When I talk-

    23. HS

      I'm building a really secure business-

    24. BL

      Yeah

    25. HS

      ... that grows three, four X, which by the way, is amazing.

    26. BL

      Which is great, which is incredible.

    27. HS

      Yeah, but it's just like not that.

    28. BL

      [laughs] So you're like, it's amazing, but it's, it's actually-

    29. HS

      Yeah, it's not that

    30. BL

      ... ah, it's amazing for 2011, right?

  11. 26:30 – 39:10

    How Clay Finally Introduced Variable Sales Compensation

    1. BL

      we, we just rolled out a variable compensation plan at Clay, right? Before everybody was just being paid a salary, whether you're the top performer or the bottom performer, right? And, and, uh, as a, as a salesperson, I saw that and I said, "Huh, okay." And like, you know, there's a lot of companies that have, have ... That have done that in the early days, like Stripe did that in the early days. And I think, uh, you're a founder-

    2. HS

      In other words, no bonuses done.

    3. BL

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

    4. HS

      Yeah, yeah. OpenAI did this too. It's fucking-

    5. BL

      Yeah

    6. HS

      ... stupid.

    7. BL

      I, I saw that and I said, "Incredible that it's gotten you this far."

    8. HS

      [laughs]

    9. BL

      "Let's figure out how, how you, how you reward and attract and retain the right talent." 'Cause like I'll give an example. We just hired a, a, a GTME, our, our version of a rep. S- you think of it as like a rep and a sales engineer, uh, rolled into one. We just hired a GTME out here in London, and, and I got off, I got off [laughs] a red-eye jet from JFK, got breakfast with her, and the conversation was, "How do we go make a million dollars here? How do I W-2 a million dollars at Clay? Walk me through the math." And that's what the best reps wanna know, right? They're like, "I, I have a target. I'll run as fast as I can towards it. Tell me how to do it." And then, and then they're like, if, if you don't have the right math, if you're like, can't walk it, walk them through it, or you don't have the right percentages, they're like, "Mm, you, you know, maybe you don't care about salespeople." But in this scenario, you're, you, you're hiring what? Your first, first two salespeople?

    10. HS

      Yeah.

    11. BL

      Here's what worked at Heap, and like, I actually really-

    12. HS

      Can I push you?

    13. BL

      Yeah, yeah. Tell me.

    14. HS

      Do you agree with me it's fucking stupid not to have-

    15. BL

      [laughs]

    16. HS

      ... tied to performance?

    17. BL

      I, uh, I, I do.

    18. HS

      Yeah.

    19. BL

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

    20. HS

      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."

    21. BL

      [laughs]

    22. HS

      Well, again, to your point-

    23. BL

      Well, I think-

    24. HS

      ... if there's no tenders-

    25. BL

      I, I-

    26. HS

      ... we're like, "Thanks, but I still need-

    27. BL

      I think what it does-

    28. HS

      ... to pay the mortgage."

    29. BL

      I think what, I think what, well, I think what it does is it just, it, it, it allows people to just, like, hide.

    30. HS

      Yeah.

  12. 39:10 – 40:37

    AI in Sales: What's Real vs What's Hype Right Now

    1. HS

      Yeah

    2. BL

      ... if I pay you, uh, if I pay you 10 cents on the dollar before-

    3. HS

      Yeah

    4. BL

      ... it, it should jump pretty significantly.

    5. HS

      But for every new deal at Clay now, do I get 25%?

    6. BL

      Uh, it doesn't jump up that high.

    7. HS

      Oh.

    8. BL

      You know what? You [laughs] ... I know, very disappointing.

    9. HS

      Why, why, why did it at Heap and not at Clay?

    10. BL

      Uh, I mean, we did it at Heap because we were the first two reps-

    11. HS

      Mm

    12. BL

      ... and they were like, "Just go fucking close this."

    13. HS

      So you can't have that high a width scale?

    14. BL

      I think it, I think it depends on the economics of your business.

    15. HS

      Mm.

    16. BL

      So, like, if you think about Clay, right, like, we pay for the data that we sell.

    17. HS

      Mm.

    18. BL

      Right? So, like, we pay per credit in the same way that, like, we charge for a credit of, of data. Um, and, and actually our, our, our economics are very, very good. Our, our head of finance is really smart about, about all that type of stuff, but, like, in some businesses, you have shit margins.

    19. HS

      Yeah.

    20. BL

      Uh, and I've worked for companies that have, you know, less, less than ideal margins, and it kinda puts a, it kinda compresses what you can actually pay. So, like, maybe that's something that you look for in the AI era, right, is, is good margins.

    21. HS

      Yeah.

    22. BL

      I don't actually know why, why we can't do that. Like, there sh- there's, there's a flat, 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.

    23. HS

      Yeah.

    24. BL

      Right? Now go, now go work your ass off.

    25. HS

      I, I, I like it. One thing that you said there kind of about, um, not great margins with AI companies, and-

    26. BL

      Yeah

    27. HS

      ... a lot of them don't have great margins 'cause they also give a lot upfront.

    28. BL

      That's right.

    29. HS

      And inference is their kind of sales and marketing cost in some ways.

  13. 40:37 – 42:37

    How Your Sales Motion Changes With a PLG Product

    1. HS

      How does your job change when kind of people have tried the product already, uh, they've got usage already, and it's not the SDR outbound that it used to be?

    2. BL

      Well, I think, I think if you... You're talking about, like, a PLG motion.

    3. HS

      Mm.

    4. BL

      Right? Um, and if you have usage, your, your job then becomes what are the next use cases, what are the next teams? You're fighting over, like, workloads, right, rather than going and landing a logo. Because if you think about, think about, um, I don't know, think about Salesforce, right? How many places, how many entrances are there for different AI tools, right? And then how much market share internally at Salesforce do they have? So, like, if you go land a logo, let's say Salesforce is on, is on a PLG motion for your company, your AI widget, right? And that, you know, you got, like, I don't know, three people in the marketing team using it, three people in the sales team, whatever, right? Your job then as the rep becomes how do I go take that market share in that company faster than any other AI company or any of our competitors can come in and take some of that? Because once they're in, then you're fighting with them over workloads versus fighting with inertia. So it's almost like can you go into an account and suck the oxyg- oxygen out, right? And that's actually how I think PLG businesses do really, really well, right? Someone comes in, they, you know, they, they're dabbling in the product, right? And you as a seller, you're like, "I'm gonna go market that internally at that account to all of the other people and pick up all of the other use cases and secure, secure that, that, the borders of that," not to be too American.

    5. HS

      Yeah.

    6. BL

      But secure the borders on that account from anybody else. It's like Risk, right?

    7. HS

      [laughs] Trump would be proud. [laughs]

    8. BL

      [laughs] No. But, but, like, you think about, you think about going and securing, securing your land in that account so that other competitors can't come in. You see, 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 gonna win

  14. 42:37 – 47:58

    How to Build Real Internal Champions

    1. BL

      that.

    2. HS

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

    3. BL

      Okay, so if you actually ask anybody, uh, on my team, uh, I hope that they don't listen to this because they're gonna groan. I, I will oftentimes just sayOkay, who, do you have a champion? And they're like, "I have a, I have a, yeah, I got a, this person's my champion." I'm like, "What are the three characteristics of a champion," right? And 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, right, if you, if you focus on honestly just the personal win, like, yo, why are you doing this?

    4. HS

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

    5. BL

      Yeah. So, like I'll give an example of, of, um, a champion of Clay at a, at a company that, that we all would know. [clears throat] Her win is she's like, "Hey, I'm becoming the AI person. I teach this AI course at the university in this large city, and I'm talking about how I'm using Clay and I'm building my personal brand, and like I kinda wanna get into like venture and investing and advising companies on AI, and like I'm leveraging what I'm doing with Clay to show that I'm that person." And I'm like, "That's an, that's an incredible personal win," right? Um, at dbt like you would talk to folks and you'd be like, "Yo, why you, why you care so much about this? This is just data transformation." And they'd be like, "But I wanna be the data guy. Like, I wanna 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, you know, a higher salary, get more equity," whatever. If you focus on that, if you could get, if you can get to that, you probably have a champion and like they're probably gonna go to war for you and they, and, and if, they have to have the other two things.

    6. HS

      Becca, I'm one of your reps. Um-

    7. BL

      Mm.

    8. HS

      I'm sorry, Becca. It's, it just slipped to next quarter. I know I said this quarter.

    9. BL

      [laughs]

    10. HS

      I know I said this quarter, but Mitsu-

    11. BL

      That never hap- That never happens

    12. HS

      Never happens.

    13. BL

      No.

    14. HS

      But Mitsubishi, they just, ah, it just slipped to next quarter. What do you say to me?

    15. BL

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

    16. HS

      Honestly, they took longer to get back to me than I thought-

    17. BL

      Yeah

    18. HS

      ... and we just didn't get it over the line in time.

    19. BL

      Ah. Here's, here's a big one. Uh, oh, uh, this actually happened to, to one of my reps. "Oh, uh, you know, the, uh, 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. Fuck." And I'm like, "Okay, well, like let's, let's break this down. Is there someone internally that could have told us that?" Yes, probably, right? So then did we talk to that person? It's like, did you talk to that person? Did you ask the right question? 'Cause they're, 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 'cause their job is not to buy software. It's to... Sometimes it is. Fair procurement, right? Um, 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," right? 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 I, we, we just opened a London office. I was talking to, 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," right? 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, it's binary," right? Like, if you're a bad champion, is it, you're really your champion?

    20. HS

      Yeah.

    21. BL

      Right? You're either a champion or you're not a champion. Like, let's be really clear about it, and if you're, if you say they're a champion, what have you seen with your two eyes tells you that they're selling for you when you're not in the room, they have access and influence over the EB, and there's a personal win, right? It's, it's pretty simple. If you don't have a champion, you're probably not gonna 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.

    22. HS

      When we sit down and we do postmortems and we do like collaborative forecasting on what we've done-

    23. BL

      Mm-hmm

    24. HS

      ... and what we've got ahead of us-

    25. BL

      Mm-hmm

    26. HS

      ... how often do we do that?

    27. BL

      Uh, every, 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 or 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," right? 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, are we making assumptions? Do we need to go back and actually... You get to the end and something happens and you're like, "I have a bad champion." Well, actually, you're back here and you skipped a couple steps, right? Let's just be real and move it back there now and go do the work to actually build the right deal. So we do that once a week. I do that with my frontline leaders on Fridays, and the way that I do it is I just model the behavior that I want them to be doing in their forecast calls, and I expect that they're in the deals in the same way that like I'm running a couple deals with reps, and it's a lot of fun.

  15. 47:58 – 53:05

    The Biggest Mistake Frontline Sales Leaders Make

    1. HS

      What are the biggest mistakes sales leaders make in forecasting?

    2. BL

      I think it, it, at the frontline, not being in the details, not being in the deals with the rep. So, like, uh, I'll give an example. I talked about John Dalton earlier. I- John Dalton is like one of my favorite people. I, I would love to work with John Dalton for the rest of my life. Um, he also lives in Santa Barbara, is very chill. John Dalton, if you asked him, "Hey, what's going on with company," he knows because he's in the deal with the rep doing the work, showing the rep, "Here's how you do a good deal. Like, 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, uh, you might ask Stacy, right? "Hey, what's, 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, right? This, the, the, the rep has specific, we have a specificLike, standardized way of writing your next steps. I can go read that too, but what are, 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, like, 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, there's a, you know, you, however you decide, you decide. Um, but that's probably the biggest mistake that I see for frontline leaders.

    3. HS

      We get that big logo.

    4. BL

      Yeah.

    5. HS

      I'll 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-

    6. BL

      Ooh

    7. HS

      ... relationship with the rep-

    8. BL

      Mm-hmm

    9. HS

      ... who's a hunter-

    10. BL

      Mm-hmm

    11. HS

      ... versus like handing off to cushy, cushy nice CS.

    12. BL

      [laughs]

    13. HS

      And then one of your competitor's hunters-

    14. BL

      Yeah

    15. HS

      ... is going-

    16. BL

      'Cause they're competing-

    17. HS

      Pray

    18. BL

      ... for the same workflow-

    19. HS

      Yeah

    20. BL

      ... in your account because you didn't secure the account.

    21. HS

      And you've got cushy CS who's now like-

    22. BL

      [laughs]

    23. HS

      ... oh, softly, softly, and the hunter's going ...

    24. BL

      I mean, look, there's, uh, you're kinda getting into the, the question of like, wha- 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 have, to sell a good deal, right, and protect your unit economics. Someone on John's team sold the 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, right? Um, so it, it helps protect the unit economics because you know that you're gonna have, you wanna go and expand that. But two, you sell a shitty deal, you're gonna renew that shitty deal, and you're probably gonna take some churn or contraction, right? And like, that's actually the model that I love because it incentivizes you, the hunter, to go and secure the border in that account, right? And not let anybody else come take your workflows.

    25. HS

      Yeah.

    26. BL

      Uh, and 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.

    27. HS

      You, you said about like, oh, the discount and then you gotta make it up over time.

    28. BL

      Yeah.

    29. HS

      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.

    30. BL

      Ugh.

  16. 53:05 – 57:24

    Is Outbound Dead?

    1. BL

      Absolutely not. No way. So, so it's funny, people, people ask this question. Uh, when, when I first started Clay, they were like, "Oh, uh, yeah, SDRs, what's your perspective?" And I was like, "I'm building an SDR team. I'm building a Clay DR team," right? 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, you know, 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, you know, a quarter billion dollars of pipeline, like, it's actually probably a little bit more efficient to just put some, you know, hungry, scrappy 24-year-old on the field, pay him, you know, a certain amount of money, and say, "Go run at these accounts," right? That's the first thing. The second thing is like, hey, you don't have an SDR team. Who the hell are you gonna promote into your, [laughs] into your closing roles? It's really, it's, it's, it's completely de-risked if you have an SDR that you're promoting. Those are the best people.

    2. HS

      So outbound is not dead.

    3. BL

      No. Outbound is not dead.

    4. HS

      Should AEs be responsible for pipeline generation?

    5. BL

      Everybody should be responsible for pipeline generation. Everybody owns pipeline. I'm out here, we, we have a, uh, we call it Clay Day on Tuesdays. You might know it as its former name-

    6. HS

      Yeah

    7. BL

      ... PG Tuesday.

    8. HS

      Yeah.

    9. BL

      Every Tuesday, I ask my team, "Hey, who can I reach out to for you?" Right? "Who can..." We have, 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. And like, it's, it's funny, you know, uh, it's so funny that, like, just the same message coming from a different mouth-

    10. HS

      Totally changes everything

    11. BL

      ... it, it, yeah

    12. HS

      Yeah.

    13. BL

      It gets, it gets a completely different response. And so, like, I encourage people to think about it. The, one of the GTMUs that I was talking, talking to, um, out here in London, you know-Tuesday rolls around, we kick off Clay day. I'm like, "Hey, what's working well?" She's like, "You know what? I'm just doing the basics. I take an account and I think about what are all of the ways that I can go and, and make contact with them. So is it a VC? Is it me? Is it you? Is it our partners," right?

    14. HS

      You get a Sequoia partner to LinkedIn message a CEO-

    15. BL

      Yeah, dude

    16. HS

      ... 100%, there's an increased chance of that response.

    17. BL

      Yes.

    18. HS

      100%.

    19. BL

      100%.

    20. HS

      One, one of our portfolio companies, the CRO comes in every, uh, month-

    21. BL

      Yeah

    22. HS

      ... and gives me like the top 10 targets, and I just go with them to the CEOs on LinkedIn.

    23. BL

      Yeah.

    24. HS

      I have a blue check mark and lots of followers on LinkedIn. I get like-

    25. BL

      Very important

    26. HS

      ... No, very important.

    27. BL

      Yeah, I heard, yeah.

    28. HS

      Very important. Channing shit on LinkedIn.

    29. BL

      [laughs]

    30. HS

      Uh, nine out of 10 respond.

  17. 57:24 – 59:08

    What AI Actually Changes in Sales (vs What It Doesn't)

    1. HS

      You said AI doesn't change SDRs, it doesn't change outbound. What does it change?

    2. BL

      Well, I wouldn't say that it doesn't... I, I didn't say it doesn't change it. I just said it doesn't replace it.

    3. HS

      Hmm.

    4. BL

      Right? I think about this, like, if I can... And, and this is like my thesis with the Clay DR team is like, let's say, uh, let's say 20- 2018, um, uh, an SDR can book, I don't know, in a, in a given month, say they're booking 15 meetings.

    5. HS

      Mm-hmm.

    6. BL

      Right? If I can arm that rep with Clay and a, you know, a Claude seat, maybe a Lovable seat, I don't know, I can tool them with some sort of AI stack, right? And now they can book 40 meetings a month. I'm gonna say, "Yes, please. Thank you." Okay? Now I wanna grow my team of SDRs from eight to fucking infinity, right? Because I see a ton more productivity. Anybody that's like, "Oh, well, you know, we're just gonna cut our SDR team in half," I'm like, "Hmm, okay. That's an interesting move," right? That's a, that's a scared play that you're making because you're saying, "I can get the same productivity for half," versus saying, "I can get this productivity and now I'm gonna go multiply that into infinity and take all the space, all the oxygen out of these accounts."

    7. HS

      Unless you... Well, 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, if you think you can replace it entirely and just hand off to an FD, you can get in infinity with-

    8. BL

      Yeah

    9. HS

      ... one tool.

    10. BL

      Uh, well, I think, how many, how many businesses do you think out there can actually replace the entire SDR process-

    11. HS

      None

    12. BL

      ... and just hand it off to an AE?

    13. HS

      Uh, right now, none.

    14. BL

      Right?

    15. HS

      Yeah.

    16. BL

      So it's like, okay, you're gonna have, you're gonna have some number of SDRs.

  18. 59:08 – 1:05:01

    Best AI Tools Becca Uses

    1. HS

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

    2. BL

      I don't know that I have particularly found the AI tool and brought it in.

    3. HS

      Okay.

    4. BL

      But here's, here's like two tools that we use pretty aggressively. Like, everybody uses Lovable, everybody uses Claude, right? Like, I was talking last night with a bunch of, a bunch of my team about like, you know, on the plane back to, to New York, I'm probably just gonna look at the Claude saved projects and just like steal a bunch of ideas. Um, the two tools that I'm obsessed with right now, Granola. Everybody's obsessed with Granola. Great... You know, they just rounded, raised a big round. Happy for them. Um, the other tool is Whisperflow. Had... Are you familiar with them?

    5. HS

      No, that's very personal. So, uh, Granola-

    6. BL

      [laughs]

    7. HS

      ... and 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 'cause no one will give them money.

    8. BL

      Oh. [laughs]

    9. HS

      Yeah, Chris is a-

    10. BL

      Well, they, they gotta think what, like, uh-

    11. HS

      Chris is, Chris is a, Chris is a friend of mine, and he basically came to me and he was like, "AI and notes, it's gonna be a thing." I didn't have any clue how, what, where, when, but like that's the thing. I'm like, I've been in Rome Research, I've been in all these-

    12. BL

      Oh

    13. HS

      ... you know. So that was-

    14. BL

      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, and, uh, my talent partner. And like, it's like very cut and dry. There's like no emotion [laughs] in the Granola notes. And Varun was like, "This do- Is this a positive? Like, was this a positive reference?" And I was like, "Yes, it was glowing." And I looked back at the Granola [laughs] notes and it was like just objective like, "Yes, Sta- you know, Stacy helped me in this deal, like blah, blah." And I was like, "Okay, got it. I'll figure out a, I'll figure out a different process." So like they got some things to work on.

    15. HS

      And then Whisperflow, to be fair, I, I never had the chance to mess with them, but I, I loved them. I used them the whole freaking time. I never type anymore. Like never type.

    16. BL

      Yeah. I, I, I... Well, and, uh-

    17. HS

      The only thing that really annoys me on the phone is the toggle.

    18. BL

      Yeah, that is kind of annoying.

    19. HS

      It's so annoying.

    20. BL

      Especially if you don't have it open.

    21. HS

      Yeah.

    22. BL

      So, hey, Whisperflow, if you could fix that for me, that would be really great.

    23. HS

      So annoying.

    24. BL

      Um-

    25. HS

      But I love that. I'm with you

    26. BL

      ... I, because think, I, I don't know if you have this problem. If I open up a, a new email tab and I just have a blank email, I get... I'm like, "Oh my God," like, "What am I gonna say?" If I can just press a button and say... Like, that's how I, I send out like a weekly update, and if I can just press a button, I sayYo squad, this is what's going on this week. Here's the numbers, here's the pipeline, like da, da, da. And it does the whole thing for me, and I just hyperlink the shit.

    27. HS

      Yeah.

    28. BL

      I'm like, "Ah."

    29. HS

      And you can add it a little bit if you're like-

    30. BL

      Yeah

  19. 1:05:01 – 1:14:12

    Quick-Fire Round

    1. BL

      [laughs]

    2. HS

      Listen, I could talk to you all day. I wanna move to a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay?

    3. BL

      Oh, okay. Yeah. We'll do, we'll do our best.

    4. HS

      Okay. So what's the worst hiring mistake sales leaders make?

    5. BL

      Uh, 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.

    6. HS

      Mm.

    7. BL

      It's actually interesting, you see, um, I don't know if you, if you saw, uh, Brian McCarthy just joined Cursor from Rubrik, right? Um, and, and actually, you know, I, I was texting with a friend last night. Uh, a lot of people are now moving from Rubrik to Cursor. Rubrik, very playbook company. Cursor, AI first company. And I, I have a ton of respect for those guys and all the, all the playbook folks, and like, I think what they've done and what they've taught the, the, you know, craft of sales is, is really, really valuable. It's gonna 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, right? But I think there's some parts that are gonna be thrown out, right? Like, uh, I'll give an example, like, uh, understanding entire business case before you do anything in the product or you show any value, like, you can't really sell that way in the AI space. So like, I'm very interested to see how that works, but like, I've worked for leaders in the past that, that they, they have a certain hiring profile, and they do not wanna deviate from that, even for high slope individuals. I think that that's, that's a mistake, because then you just get the same, you get 100 of the same kind of person versus people who are gonna actually push the envelope.

    8. HS

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

    9. BL

      Um, 12 months ago, I actively resisted using AI. I was like, "I think it's gonna make people dumber. I think that," you know, you, you see, you see some folks that just ask Claude the answer rather than reasoning about it themselves, and I was like, "Ooh, I don't love that." Um, o- obviously, like now I work at an AI company, so maybe, uh, [laughs] maybe I'm a hypocrite. But like, basically I went from saying, um, "Fuck that," like, "I'm not gonna use this thing," like, "I've got a brain and I'm gonna use it," to, "Okay, how can I, how can I offload some of the things?" Or like, "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?"

    10. HS

      Do sales teams have to be in person?

    11. BL

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

    12. HS

      In an office.

    13. BL

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

    14. HS

      Are you not pissed when you go in and other people aren't in? Like, Friday is the new holi- like weekend now

    15. BL

      [laughs]

    16. HS

      Especially in Europe.

    17. BL

      I know, yeah. Tomorrow's Easter-

    18. HS

      Like, Friday is like work from home Friday?

    19. BL

      Yeah.

    20. HS

      Fuck off.

    21. BL

      Yeah. [laughs]

    22. HS

      It's not work from home Friday.

    23. BL

      Um-

    24. HS

      Like, I, I would never let ... Work from home Friday or Monday is basically, it's an extended weekend.

    25. BL

      It's a three-day weekend.

    26. HS

      Yeah.

    27. BL

      I, I, I, uh ... Look, I don't track attendance, and, like, if you're a produ- if you're productive, you work from wherever. You get a little bit of flexibility. But if you're underperforming and you're not in the office, we're gonna have a conversation.

    28. HS

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

    29. BL

      I, I think everybody would say this. I think, uh, uh, people feel like they don't want to be sellers. So, like, you know, maybe you're a product leader and you're like, "Ah, mm, I don't really wanna go into sales," because it feels a certain way.

    30. HS

      Mm.

Episode duration: 1:14:22

Install uListen for AI-powered chat & search across the full episode — Get Full Transcript

Transcript of episode d_nWswprCqk

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome