The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
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What’s the most common mistake people make when negotiating their compensation?
What's the most common mistake that people make when they're negotiating their comp?
Often we'll hide behind the easiest communication channel possible. I might email you my demands. The problem with that is I can't control tone. 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.
A lot of people listening to this are just afraid to ask for more. I'm gonna come across as greedy. It's all gonna fall apart.
look at the money that the company's making in comparison, like you're not being greedy. It doesn't have to be such an aggressive thing, or it doesn't have to be confrontational. The simplest advice is what's the chance there could be a little more? That's not greedy at all.
The corpse your philosophy is make it very clear to the company, here's the pain I will solve for you and here's why it's worth paying me this
Much more these companies have significant leverage over you. They know what people make, they know what others make, they know what they'll accept. You have to understand what value you can create. And if you understand that value, you can have that conversation with confidence.
Today, my guest is Jacob Warwick. Jacob is a professional negotiator. He works behind the scenes with his clients, mostly senior tech execs, professional athletes, and Hollywood celebrities, and he helps them navigate their most complex career negotiations, including their comp, their bonuses, and investments, also MA and takeovers and enterprise sales deals and more. He's helped his clients secure over $1 billion. Dollars in additional comp. And he's told me that he's negotiated against a number of guests on this podcast. He is very much under the radar, is not on social media, rarely does interviews, and in this exclusive conversation, we get super deep on the specific tactics and psychology of comp negotiation, including why you should never negotiate over email, who should speak first when the question of comp comes up, the most common and costly.
mistakes that people unknowingly make when they're negotiating comp, and so much more, Jacob is also just a truly stellar human and I'm very excited to be sharing his story. Don't forget to check out Lenny's productpass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Let's get into it after a short word from our wonderful sponsors. This episode is brought to you by Orcas, the company behind Open Source Conductor, the orchestration platform powering modern enterprise applications. Modern systems are built on microservices, APIs, and event driven architectures, but legacy automation tools can't keep up. Siloed low code platforms, outdated process management, and disconnected API tooling break down under real world scale and constant change.
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That's O-R-K-E-S.io slash Lenny. This episode is brought to you by Mercury, radically different banking loved by over 300 Entrepreneurs, including me. I switched to Mercury from Chase over a year ago, and it is such a profoundly better experience. It's like an actual product person built a bank versus a banking person building a product. It is fast, it's elegant, it is super easy to set wires, to track my spending, to set up triggers to move money around when accounts get low.
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Chapters
8 chapters
1
What’s the most common mistake people make when negotiating their compensation?
0:00–4:35
2
How does Jacob Warwick introduce himself and his negotiation background?
4:35–21:03
3
Why do people leave money on the table and how can a simple “what’s the chance there’s a little more?” unlock extra pay?
21:03–33:47
4
When does negotiation really start and why timing, home‑field advantage, and power matter?
33:47–1:00:41
5
How can I treat my job search like a product launch?
1:00:41–1:08:58
6
What steps make the interview process frictionless and collaborative?
1:08:58–1:20:47
7
How should I respond when a negotiation stalls or an offer is rescinded?
1:20:47–1:39:41
8
What’s the first tactical move to boost my compensation after getting an offer?
1:39:41–1:54:51
Speakers
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