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Jacob Warwick: evaluation

15 Mar 2026 Lenny's Podcast The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)

“I think oftentimes because we're working soulless jobs that we don't believe in and we're just trying to make do and survive for our families.”

— Jacob Warwick

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Speaker
Jacob Warwick
Attribution
Verified speaker
Claim type
evaluation
Recorded
15 Mar 2026
Publisher
Lenny's Podcast

Transcript context

…This is great. Patience is more important. Things need to slow down. Haste equals risk. The slower you go, the more opportunity you have to collect information so that you can build a compelling case. That's important. I am a big believer in Aristotle and his principles of rhetoric in ethos, pathos, logos. And so I've mentioned a little bit of this in their more common tone of logic, credibility and emotion. Timing is another one that we don't often talk about. Kairos is important, but too many executives lean on credibility and logic because we're trained to do that. We don't show emotion. We don't show the authentic side of ourselves in corporate. I think oftentimes because we're working soulless jobs that we don't believe in and we're just trying to make do and survive for our families. I think there's a greater need there. The emotional side is where a lot of deals get unfair. So if we understand how to tap into that... I want to say Chris Voss... I keep mentioning Chris Voss, but I think he calls tactical empathy, right? Which that sounds more Machiavellian than anything I've ever said. But understanding those motivations and understanding how to play on that can be important. So when we talk about giving people a positive reputation, we're playing into some emotions here. So if I'm a female negotiating with another female, I might say, "I appreciate that you've always been an advocate for women and you support one another. That's something I respect about you." And then their comp comes in lower than a man's comp. You can call them out on that and say, "If you were in my shoes, what would you do?" That's one of my favorite lines. "If you were in my shoes... Go backwards five years in your career. That's where I'm at right now. If you were in my shoes, what would you ask for?" I love that when negotiations stall also, right? "You know what's possible here. You know what levers we have. It sounds like we're capped out here. If you were in my shoes, what else would you explore?" And you start to go that route as well. The other piece is this is a collaboration, not a confrontation. So if I could give visual advice, oftentimes... This is why it's also could be difficult in a Zoom. You and I are face to face. We have this problem between us, right? That's an adversarial position. I want you to physically pretend that you're in the same room and I walked to your office and I put my arm around you if you're comfortable with it. And instead of us arguing over something, we're whiteboarding a solution together. I want collaboration in that. That's how we break down walls and barriers because you're sharing information, I'm sharing information, those types of things. I think that was four, maybe it was five. Another one is make it about we, not about me. So another severance conversation with a chief marketing officer, this is a $200 million private company a couple years ago. So she comes in, she gets offered $340,000 base salary, 30% bonus, equity. So another severance conversation with a chief marketing officer, this is a $200 million private company a couple years ago. So she comes in, she gets offered $340,000 base salary, 30% bonus, equity. We tried to push on all that and the CEO said, "Look, one of the things I pride myself in is that everyone here has $340,000 base, 30%, and the same equity package." Everyone on the executive leadership team. Now, she was getting pulled from a hot company, which is risky because she was safe there. She actually was getting a raise coming to this company, so we didn't need to push on more money. What we went for was severance protections. And so we asked, standards about six months, maybe plus another month for every year served. And the CEO is like, "Oh, we've never done that before." And so instead of it being like, "You're negotiating the terms of your divorce before you get married, that's what's awkward here." We said, "Well, given that we've had a problem with talent being poached and going elsewhere and we just did a big riff, wouldn't it make us look good to proactively give everyone on the executive leadership team six months to show that they're safe and committed to the company?" And then we fed that idea to the CEO so the CEO could look like the hero. More importantly, when my client came into that company, she looked like a hero because everyone is like, "That's the woman that negotiated us all severance protections." So we made the company, we used the company's equitable policies to do that. Now, I will say that's not common. So if folks are like, "Bam, that's fantastical. That may not happen." Especially with private equity, it usually doesn't. There are ways that we want to appeal to a humanity more so if we can. Bonus point. I know I'm monologuing a lot. Don't be afraid to get creative. Creativity is interesting. And one time we got someone at G-Wagon after being maxed out on comp. I like this story because it's so out of this world that you're not going to get a G-Wagon. I promise you, it is likely not going to happen. But we had this CEO who had two offers that were both 2.4 million and they were stalled. First world problem, right? Tiny violin, 2.4 million a year, the CEO deal. And she told me, and this was just a joke. This wasn't some Machiavellian plan. She was like, "Look, I don't know which to choose. They're both maxed out." And I was trying to say, "Which one would you like more?" She wasn't giving me anything. They're both fine, whatever. And I said, "Well, I don't know. What kind of car do you like?" And she said, "Oh, I love Mercedes." And I was like, "Tell them that," jokingly, because they inevitably came to, "Look, what's it going to take to hire you?" And she's like, "I don't know. Maybe a company car." And they said, "Well, what kind do you like? " And then she said, "Mercedes." And they're like, "Done. What model?" And then she's like, "Oh, a G-Wagon." What happened was all the budgets were capped, but it was a company write-off to have a 6,000-pound vehicle. So it was a $350,000 car added to her contract that was a company write-off that reduced the tax expense. So that's not going to happen.…

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