Warwick: Never negotiate compensation over email; always use video or in-person
Jacob Warwick · He's negotiated $1B+ in executive compensation. Here's his playbook. | Jacob Warwick · Mar 15, 2026 · at 17:45
Executive compensation coach Jacob Warwick discusses pitfalls in high-stakes job negotiations with Lenny Rachitsky.
0:00 / 0:47exact quote · 47.3s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“So often we'll hide behind the easiest communication channel as possible. So I might email you my demands 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. And the CEO that reads it's 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, you know, 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. Every step of the way.”
quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →
More from Jacob Warwick
Warwick: Asking 'is there more' yields 20% higher job offers
“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 100,000 dollar offer, a 120 could be there just from a si…”
Warwick: Negotiate compensation directly with P&L owners, not recruiters
“Oftentimes we also try to negotiate through recruiters, right? You could do that. I, Jake, 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 hap…”
Warwick: Product and engineering leaders negotiate worse than sales and marketing
“I found that product, 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 and the more extroverted types.”
Warwick: Using third-party agents in corporate America dilutes executive presence
“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 of corporate America right now, right? Now, if that happens, it almost dilutes the leadership and presence of the …”
Warwick: Refusing a CEO's proposed meeting time increases a candidate's attractiveness
“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 six o'clock in the morning, get your ass up, get that presentation and go. You need to say, I'm not available at that time. I'm in, and you…”
Warwick: Up-leveling to VP increased director offers from $200k to $1.1M
“There was three folks last year that were in ranges of 185 to two 85. 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 w…”