YouSaid · the spoken record

Jacob Warwick

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144
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2026-03-15
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2026-03-15
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  1. “Then they're trapped. They have to say, No, I don't respect you. I have to do this. Or they have to say, you're right. Like that makes sense. Let me move you forward or not. Another option. You don't necessarily know if you're the best solution for that fit or not. And so we're obviously very ingrained when a recruiter reaches out to you and they say, look, we're going to pay 120 and you make $150. And you're like, oh, I'm not interested. That's not even close. I would recommend continuing that process any way to see as practice what you can negotiate. You can always say no later, right? Just because having that practice is going to make you hundreds of thousands, if not millions more in your career.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “We have the ability to push back and practice these difficult conversations, you will increase your power and you'll land at a higher rate because of it. So can it get frustrated? Absolutely. But if somebody disrespects you through that process, doesn't that give you an indication of who the company's working with? Now, again, I might accept that because I need the money. I understand. But it's very telling how somebody's going to treat you depending on very simple pushbacks. And one behavioral psychology hack here is we give someone a positive reputation that they want to withhold whether they deserve it or not. So in this instance, you'd say the recruiter, I want to thank you for being an advocate for me and for respecting that I won't share compensation figures right now. I appreciate that.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “You are and about your kids. We say, What do you do for a living? And when you are stripped of that title, it's uncomfortable. And we want that pain to end. And so we give in to these demands because it's an authoritative figure and we want that pain to go away. If we have the finances and the luxury of being able to say no, we increase our power”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “Couple things about power, right? So, if you have the ability to say no, you have infinite power, right? The nuance changes when you don't have a job and you need to pay your mortgage, you might answer that differently because you want something. This isn't a shame somebody who's feeling that way, right? If you're out of work for six weeks in San Francisco, you're homeless, right? That's just the reality of the situation. So if I got to say a number to get a job, I think that's fine, right? But understand that once you're employed in somebody's asking you and your needs are already getting met, why do you need to get pushed around? This is one reason that it's easier to find a job when you have a job. Now, I think this is a myth for what it's worth, but this is easier because naturally your needs are getting met financially to a degree. So naturally you negotiate more confidently. When you're out of work and you have the uncomfort of being out of work six months, 12 months, 18 months, you have an identity tied to a chief product officer role or a VP of product. That's your identity in our country. We don't ask who you are.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Thought like if I made a lot of money, it would make that pain go away of not liking my job. Turns out that was a fool Zaren, but that's the story for another time.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “The reason I learned this is I used to be a marketing manager making $12 an hour in downtown San Francisco for series A companies, not knowing that $12 an hour wasn't a lot of money. I just didn't know any better. But then I left out marketing managers and I saw that they made 60 grand a year and I suddenly got offended at how little money I was making. Then I got promoted to director in that period and was making $14 an hour good for me, right? And then I saw that marketing directors were making $110,000 at the time. So when a recruiter called me, I pulled that. I didn't want to tell them I was making $14 an hour. They'd be like, who is this kid? He's not very good. That's fake title. And instead, I said, what did you have in mind? And they said, oh, we're looking at $110 to $130. And I'd say, oh, I'm on the upper end of that now. And so I went from $14 an hour to $120,000 a year in a single jump, just like that. That changed my life, one negotiation, one of the reasons I'm so passionate about that. I hated the marketing work for what it's worth.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “And then typically they'll say, Yeah, it is going to be a problem. I just need to know a number, right? Now, I mean, this is what it's very uncomfortable to do this back and forth and to say no, especially Americans have a hard time saying no. I have noticed that other cultures can be more direct and just say, no, I'm not going to do it. So be it, right? So culturally, there's a lot of differences in how this conversation happens. And so they say, look, We need a number from you. You might say, Look, I'm uncomfortable doing that right now because I don't understand the scope of the role. Can you help me understand what you had in mind?”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Nine times out of ten of recruiter reaching out to you is going to ask that number, right? One time out of 10, they're going to just focus on the value creation. Those are the ones you want to focus on the best possible. But it could be confusing because so often you get a different side of the story, more of the commodity type stuff. So typically I'd recommend you answer, right? I don't talk about compensation until we're ready to make an offer. It sounds like we're pretty far away there. I'd love the opportunity to learn more about the team, understand where the value comes in and proceed kind of down that path to make sure we're a good fit. Is that going to be a problem?”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Yeah, there's a decent amount of nuance in this, too. So, one thing you should realize is that. Especially earlier in your career, they're going to push on this harder. And that indicates that the person asking is really more looking for a commoditized or a price sensitive hire. That can be okay, right? There's nothing wrong with sharing your number and getting a deal that moves the needle early in your career and even middle of your career. That changes the higher up the ladder you go. And this is one of the reasons I want to share this is that what got you here won't get you there. So things start changing as you mature in your career. And so when you're working with a top recruiter, they don't ask you about calm. They won't. The problem is top recruiters only reach out to you when you're very well known and they don't reach out to you very often. So it's very difficult to optimize for inbound attention the higher up you go unless you become very popular. And then what happens is you share less information because people come to you in a different capacity.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “My son does that too. I go, do you want a banky? And he goes, Five binkies. I don't know if we have five, and he's all 10 binkies”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Absolutely not. I would not recommend that, especially if your wife knows what you do for a living and hears you on the phone all the time and you try to say, what's the chance? And she's like, no chance. Don't pull that on me. I know what you're doing, right? And toddlers are terrorists. So I don't, I haven't figured that one out. I resort to bribes and maybe that is a little Machiavellian on the toddlers. You can be out of your mind working on that. Yeah, don't recommend it with your spouse.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “It's really nerdy. I know. I'm like obsessed over it in a weird way, but I don't know. It's been kind of baked. That's been helpful.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “That movie, like that movie, could make $50 million. You think one million for writing was worth it, or someone who controlled the creative there? I don't know, 50 to 1 value exchange. Why not push for more? Why not put some milestones in that if this movie makes more than 50, my milestone is increased? This is how like Tom Brady had his contract at Tampa Bay, right? Win eight games, get a half a million dollars, win 12 games, get a million five, go to the playoffs, get an extra this, win the division, get this, get this, get to the Super Bowl. X, win Super Bowl MVP, two and a half million more. So performance-based triggers.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “1.3 million. And the studio said, fine, we'll do a million, and they settled at a million. And I find that really interesting because the studio came up 300,000 and the attorneys lost 300,000. So you split the difference right in the middle. So if the attorneys said 1.5, would the deal have coming at 1.1? If the attorney said 1.7, would it have come in at 1.2? How do we know? The way I see it is those attorneys weren't aggressive enough. We didn't find the ceiling there, did we? That was lazy negotiating. So it still made the client 300,000. They were excited, right? The attorneys were excited. They made more on their commission. The agency was excited. They got 10% of that. But we didn't find the ceiling, did we? That was lazy negotiating. So those are things that you've got to slow down to really understand where is the value being made here.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “Sometimes, again, it really depends on the leveling. If you are very senior, I typically don't want to re-anchor with a number because you should ever be so sure of what you're worth that you wouldn't accept more. Right, and when you anchor, that's the ceiling. And what often happens is naturally they want to split the difference. And so I'll have a quick, there was a quick Hollywood story here. So we had a writer who had a $700,000 contract, right? So $700. And the agent that I was working with was saying, like, this writer has the most aggressive attorneys in LA, right? They're super aggressive. And I said, well, how do you know, first of all, well, that's what they're perceived as. So the production studio offers this writer 700. The attorneys come back and say, we want 1.3.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “Would start with what's the chances a little bit more here? I was expecting this, right? Again, more nuances because if you open up what you're looking for too early in the conversation. That can be difficult to come back from later on. It's not entirely egregious, but one of the first things out of a recruiter's mouth is how much money do you want to make? Which is eerily similar to an illegal question, which is how much money do you make, right? But if you say, what do you want to make, then it's okay. And that's where a lot of people get hung up as well.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “What's the chance we can come in and restructure the comp for the type of talent we're bringing in here? And so this is a line that we used. There was three folks last year that were in ranges of 185 to 285. That deal landed at 1.1 million when we were done with increases in stock, big cash increases. Two deals that were comped at 600 that landed at 1.1 and 1.2. So doubled from that. And these were situations where the roll started at senior director and were upleveled to VP because they were reaching for top talent in that situation. So there are opportunities where it's easier to steer if you're really, really good, right? I can see why some listeners are like, well, I'm not there in my career yet. In that case, this is just how it gets done, right? This is how bigger moves happen. It doesn't mean you can't push for maybe 20% more naturally.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “Maybe they say, Well, what did you have in mind? It's like, well, what's the chance you can share what the range looks like for this and what type of performance did you expect for each of these levels? Or they may say we comped you in the middle part of the range, right? You might say, what does the top end look like? What must I do to fit those needs for you? Can you help me understand? Now, for a lot of folks, especially in this market, and if we talk about what it was like in 2021 versus what it's like now, there's some overleveling that's happened. So there are people that are C-suite going back to VP and VP is going back to directors, especially as they go to bigger companies. Oftentimes I'll say, you know, as we had this conversation, I'm likely a little more horsepower than you anticipated.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “Now, oftentimes, the higher you anchor, the better you're going to perform, which can be frustrating because you don't necessarily want to be like, oh, I increased it 40% or anything like that. Now, this is where a lot of nuance comes in. So we might say, you know, come back three days later, want to have the conversation. Let's take a walk in the park and talk through it, right? You know, I got to be honest with you, where this offer stands right now. I don't feel comfortable moving forward. It's a little lighter than I expected, right? I may start saying something like that. And then just wait and see what they have to say.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Working together in a couple weeks, right? So the point is you have to sell that the deal is going to be done, which helps them feel like Going to move forward regardless, right? So any ask that you make is not going to be egregious.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “So, first, we want to approach with gratitude. We're thankful that we want to move forward. So, Lenny, I appreciate you making me an offer, right? I'm excited to work with you. We want to show enthusiasm, which also shows some confidence. We have to show that the deal is going to get done, even if you're on the fence about it. Now, it's not to say you're so excited that it's a sure thing and you're not showing that you're disappointed, even if you are. So I'm grateful. I'm looking forward to working with you. I want to review this over the next couple of days. I'll talk to my wife about it. Talk to an advisor, so-and-so. Later on, when you're a high-level executive, you're talking to legal, you're talking to advisors, you're talking to a coach, you may have five or six people see that, right? Employment lawyer, all that. That stuff is expected, right? So you're going through the process. I'm going to take a couple days to process this. I'll get back to you. I may have a couple of questions, right? But we'll loop back and it shouldn't be a problem. I imagine we start.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Can be, you know, but if I'm a product manager and I'm talking to a director, that may not be possible. It might just say, look, you got to come into the office, you got to do this. When I'm talking about a C suite level, you could pull them out of the office. Hey, let's go get drinks. Sometimes these deals are closed at 8 30 at night after a concert or something like that. So it's easing that situation. That being said, it doesn't mean you couldn't try. It's like, hey, I've got a couple of questions. Are you open to take a walk down AT&T Park and have a conversation about it? You can pull.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “Between each other, we're walking side by side. So it's almost like you could put your arm around the other person. You're solving the problem together. These sound like minor. Things to consider, but the body language and the tone and the collaboration and the energy starts to flow more naturally when you do, this is all behavioral psychology, right? And so what funny story, why I found out OpenAI did that was because they didn't want any executives going into the office because it was such a mess. It was like the biggest startup you've ever seen. So I used to joke that it was two midgets in a trench coat pretending to be a real company, right? So anyway, the point was let's take them to a place where we can control and have an advantage over the conversation. So that's a way that you can think about where are you going to feel most comfortable? What hours of the day are you most comfortable? If you can bring someone to a lunch or a coffee where you're on even playing field or even your home field, you will perform better in those situations and you have more control over that than you may think.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “And you read your own body language. I'm strongest between the hours of 10 a.m. and 1 p.m. I want a meeting in that time. So I will say I'm unavailable until that time becomes available. That also communicates scarcity and that you won't get pushed around. So it's scary to do that, to say no to the CEO. I'm actually only available here. That also creates a rubber band effect that makes you more attractive. And so oftentimes, actually OpenAI did this, which is funny. And I didn't realize what the reason was, but I had some clients interviewing for C-suite roles at OpenAI. And so pushing Sam Altman around a little bit, which I'm okay with. I'm okay with that. But so they used to walk outside of the office and just walk downtown San Francisco instead, right? You take someone out of the element, you get the endorphins going, you're walking and talking. The important piece here is instead of you and I being confrontational.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “There are situations, especially at high levels, more deals are closed on the golf course than they are in a boardroom, right? So there are situations where you pull someone into a different element. This is called home field advantage, right? So if you go to a company to have a conversation, you're out of your element in a situation where you may not perform your best. The other thing people don't do is they don't control the time of which they have a conversation. CEO wants to hop on at 6 o'clock in the morning, get your ass up, get that presentation, and go. Need to say I'm not available at that time.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “People negotiate with the wrong folks. You have to go to the one who has skin in the game, who controls the P&L, who controls Ibito. What's their motivation? That's who you want to talk to. And so some people might also have a concern with, well, how do I go around the recruiter? I don't want them to look bad. We have to do that respectfully, and now we need to plan what that communication looks like. And so the important thing here is just because it's uncomfortable doesn't mean you don't need to do it. It just means you don't know how to do it. So when something's uncomfortable, you have to run towards that because that's where the growth happens.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “Step of the way. Oftentimes, we also try to negotiate through recruiters, right? You could do that. I did the thing, Jacob. I talked to a recruiter. I spent a half an hour explaining it. The problem with that is you're playing a game of telephone. So the same thing happens. I explain it to the recruiter. I get the tone right. The recruiter goes to the CEO and says, that bastard wants more money. And that's all they communicate, right?”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “And the CEO that reads it in the airport security line and pissed off, and they read it, they might be like, that bastard wants more money. That's all they take away. Even if you perfectly worded it, you got it all as clean as it can be. If you catch them at the wrong time, you have no control over how it's received, right? So it's always better to have at least a video call, if not in person, so you can share tone, you can read body language, you can correct.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “That value chain across the board. Another mistake that people make, and you mentioned this a little earlier, it feels uncomfortable to get quote unquote confrontational or to feel like you're asking for too much. So often we'll hide behind the easiest communication channel as possible. So I might email you my demands, right? Or my negotiation. And the problem with that is I can't control tone. I can't control, especially when you're negotiating at high levels. If I push back.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “And you can see, and it would like it, it was wildly consistent. It was almost frustrating. But anyway, what you're putting out into the world, the narrative you share publicly starts to become how you're known, your reputation. If you're positioned as a commodity, you will be treated like a commodity, right? So oftentimes the less you share is better because when you're on the phone with somebody, you can correct the narrative and steer the conversation where you want it to go versus have to live by the sins of what you did 10 years ago, as an example. So the things you share with recruiters, they take notes. When a recruiter calls you and says, hey, Lenny, how much money do you expect to make? And you say, oh, you know, 225, that sounds fair. Five years later, they call you and they expect you to make 225 again, not recognizing that you've grown exponentially since then. So everything you communicate starts to serve as...”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “Don't understand when it starts. So it starts much sooner than you think. So I've got myself in hot water with this before too because a LinkedIn profile in your resume is a snapshot of what you've been in the past, but it doesn't help you negotiate in the forward, right? So if somebody can say, oh, I'm looking at Let in, I'm looking at product manager. If that's all they saw, they're not going to know all this work that you're doing in the future moving forward and what your visions are, things like that. stamp you as product manager Lenny, right? Now your media mogul icon, whatever, right? But there's a gap to have to fill, right? So the things you say on LinkedIn serve as a perception. The headshot that you have serves as a perception. I used to joke that I could scan profiles. I would know how much money someone made by the quality of their headshot.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “To me, we draft it together. I usually test my clients' instincts first rather than just doing the work for them, test their instincts, polish the language, because every step of the way is a negotiation. Now, this also slows the process down. We want to go slower, and I'm sure we'll talk a little bit more about that in the podcast who Haste equals risk. So as you slow down, oftentimes we want to take a couple of days to respond, not to be a jerk or belligerent or to manufacture some fake urgency.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “Would call it fingerprintless, and there's a reason for this. So it's not yet popularized. Maybe it will be with some of these AI ICs and these hot scientists are pulling down $100 million contracts. Maybe this will change soon. In Hollywood, you have an agent negotiate on your behalf and they kind of are serving as that middle mediator. That's not common in the corporate America right now, right? If that happens, it almost dilutes the leadership and presence of the executive. And so how I work is similar to an attorney where all correspondents goes through me before it goes to the end recipient. So let's say that you're going to talk to the CEO, you call me first. We prepare the game plan. We strategize. You then perform, then we debrief. Then the CEO sends you an email. That email comes.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “Won't mention any names. Some recently were in the realm of 10 million plus on increases in compensation across a team of just a handful of folks. Again, Fortune 500. But the alternative was lose them to competitors and have the stock drop after the CEO made announcements publicly in their earnings calls. And so they don't know that it may have cost them 10 million today, but it saved them 300 plus, 300, 500 in this business process. So the success will be there. And I would say. Almost anybody would pay $10 to save $300.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “Person is usually costs hundreds of thousands. And in some of the realms that we navigate in the Fortune 500, it will cost millions, if not tens of millions, to replace the lost IP there. So the argument here is it's okay to get creative, reward it when you see it, right? I'm not suggesting give everyone everything in the company and totally ruin your business model. But if you want to be competitive, be competitive with your pay as well.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “Understand why you don't want to do it because it's hard. It's hard to make this, and everyone also thinks they're top talent. And when everyone thinks they're top talent, somebody's got to be lying, right? It can be difficult to understand that. So those that I found are more confident to push towards performance-based tend to have more skin in the game, tend to want to stick around and see that success happen. Those are the types of people I want working for me if I want to be a very competitive organization. I have started to have these conversations with a couple of Fortune 500 companies, as well as some talent consulting companies, think big recruiting firms, where they've brought me in to advise on the comp committees so that they can get more creative with their structure so they don't lose talent. Because nobody wins when you hire a top performer and they leave in 10 months. The recruiting firm loses their pay, right? Their performance pay. The company now has to go back and replace that.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “Sense there. So oftentimes, some of the ways that we're breaking the boundaries of compensation isn't necessarily advocating for a busted base comp level and bonus percentage. Oftentimes we're putting performance incentives, milestone triggers. If the company grows to 100 million ARR and I contributed this to it, what would that outcome look like? Would that be another tranche of stock or would that be cash or would that we're getting more creative here? And so what's interesting is for the longest time I had a difficult time advocating for this. And having been a CEO and founder myself,”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “So, I will challenge them as well. Now, how important of a priority is top talent in maintaining and retaining top talent to you? When you're thinking about how quickly the speed of innovation is happening, you've had a lot of great AI guests on the channel recently, right? Like the exponential curve of growth is increasing. If you hope to stand a chance, you need to attract the top talent and you need to keep that top talent because it's very expensive to replace them. I'm not suggesting that people beat you up for the sake of beating you up. So this is a myth about negotiation that's adversarial. What I teach is how can we be more collaborative? So the conversation is, look, Lenny, as a founder, can you help me understand what's important to you? The value that this work will drive. And then naturally we'll come to terms that make a little bit more of a value exchange.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “It feels a little bit more like play with strong compensation. You don't always need to negotiate hellaciously for the top of the band or break the bands just because you can, right? This isn't to be greedy, right? But it's just to understand that this value exchange isn't fair for you regardless of how it works. The path to wealth is through ownership, right? And as a W2 employee, you're being taxed heavily. And it makes sense to push a little bit in this context. That's typically where I start. I want you to just have the confidence to know that it's okay.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “Yeah, a couple things here. So, first of all, usually a company is extracting much more value out of you. Naturally, like five to one, ten to one, 100 to 1, right? If you're, I know the audience is primarily product here. I mean, you're developing products that have infinite scalability in some capacity that's going to make the company a lot of money. And they're a big piece of that. And product tends to be rewarded fairly well, right? But when you look at the money that the company's making in comparison, like you're not being greedy. And if you understand that value exchange, you can have that conversation with confidence. That's not to say that being a tall poppy isn't risky, that's the term. You overnegotiate? I would rather my clients overnegotiate reach a couple rungs up on the ladder and they get slapped down, they're still failing forward, and they're growing in some capacity. And if you can ideally align work that doesn't feel like work.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “There's a couple of sides of the business, and everyone tends to negotiate a little differently. So, you looking back at your career and say, you know, the great Lenny. A tough time pushing back. I think that's actually inspiring for a lot of the listeners to see that you're not alone in feeling this. It doesn't have to be such an aggressive thing. Don't have to be confrontational. The simplest advice that I can give you is what's the chance there could be a little more Not greedy at all. That's just a simple ask. And even that 20 30%.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “On an increase, we have seen as much as 100, 200, 300, 400 percent increases from initial offers, most notably breaking salary bands, which we all treat as gospel, which is something we'll probably talk about through the course of this podcast today. Those that challenge authority and challenge in a meaningful and collaborative way will win more than those that don't. And what's interesting is. I found that Product leaders, engineers, designers, some of the more tend to be more introverted and thoughtful types negotiate more poorly than the obnoxious marketers and revenue leaders in the more extroverted types. And it's frustrating because if you look back at the last 25 years or so, product has really defined the tech generation in so many ways. This isn't a discredit marketers or anything like that. It's just to show that”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “So typically, what I've seen is, even without my help, just general pushbacks, not aggressive, a simple, what's the chance there could be more here kind of pushback. I mean, that's about as easy as it can get. You get the offer, you say, what's the chance? There's a little bit more. Almost always see a 20% improvement on that. And that is across the board from earlier stage positions. Let's say they gave you a hundred thousand dollar offer. 120 could be there just from a simple pushback, which is when you're making that kind of money, that's life-changing, right? I've noticed that when you make a million dollar W2, same pushback, 20%, sometimes more, just on the what's the chance, depending on how well you navigated that interview process. Now on average, when I'm calculating out, what I'm looking for with clients is about 40%.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “I'm very happy to be here and thank you for interfering with my sleep all week out of my excitement. Usually it's my newborn and toddler, but this time I was waking up at three in the morning thinking about, and it's going to be a great chat. So I'm very excited. Thank you for having me.”

    2026-03-15 · Lenny's Podcast · The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator) · IDENTIFIED FROM THE TRANSCRIPT · source