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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)

“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.”

— 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

…I love how tactical we're getting here. Following this thread, the advice here is when you get an offer and you want, and you should... Basically, you're saying you should always negotiate. In some way, you should push back. Your advice here is don't do it over email, make sure you find a way to do a video call with essentially the hiring manager or the person that has skin in the game, like the finances and the budget. There are situations, especially at high levels, more deals are closed on the golf course than they are in a boardroom. There are situations where you pull someone into a different element. This is called home field advantage. So if you go to a company to have a conversation, you are 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 6:00 in the morning, get your ass up, get that presentation, and go." You need to say, "I'm not available at that time." And you read your own body language, " I'm strongest between the hours of 10:00 AM and 1:00 PM. 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. It's scary to do that, to say, "No," to the CEO, "I'm actually only available here," but that also creates a rubber band effect that makes you more attractive. 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. So they used to walk outside of the office and just walk downtown San Francisco instead. 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, like negotiating 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. 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 the biggest startup you've ever seen. I used to joke that it was two midgets in a trench coat pretending to be a real company. 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. So the advice there is try to get this conversation out of their office.…

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