The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick

What's the most common mistake that people make when they're negotiating their comp?

Often will 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."

But when you 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. 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 core to 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.

[gentle music] 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 M&A, and takeovers, and enterprise sales deals, and more. He's helped his clients secure over one 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 lennysproductpass.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 Orkes, 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. Orkes Conductor provides a production-grade orchestration layer for coordinating microservices, APIs, data pipelines, human tasks, and agentic workflows with deterministic control flow, retries, observability, and governance. Built for enterprise scale, Orkes supports visual and code-first development with built-in compliance and reliability. Through a built-in MCP gateway, AI agents handle reasoning and decision-making while safely accessing existing APIs and internal systems as MCP tools. This enables agents to operate across enterprise environments and scale from demos to production, orchestrating systems, agents, and humans together to deliver smarter outcomes faster. Learn more at orkes.io/lenny. That's O-R-K-E-S dot I-O slash lenny. This episode is brought to you by Mercury, radically different banking loved by over three hundred thousand 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. We moved all of our invoicing to Mercury, and it is such a smoother experience than anything else we've tried. It's also really easy to grant people on your team just the right amount of access to help take work off your plate. It's free to get started. No in-person visits. No minimum balances. The product also flexes to all sizes of company, from startups to large enterprises. Just visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Columna Members FDIC. [gentle music] Jacob, thank you so much for being here. Welcome to the podcast.