He's Negotiated $1B+ in Comp.
Here's His Playbook.

Jacob Warwick

Professional Negotiator · $1B+ secured for clients

CAREER · NEGOTIATION

The Ask

The Simplest Line in Negotiation

"What's the chance there could be a little more?"

That one sentence, not aggressive, not confrontational, delivers a 20% improvement almost every time.

20%

simple pushback

40%

with pro help avg

The range Jacob seesJacob has seen 100%, 200%, even 400% increases from initial offers, especially when salary bands are challenged.

Framework

The Four Moves He Comes Back To

Companies know what everyone makes, you must know your value
Lead with the pain you eliminate, not the title you want
Salary bands are treated as gospel, they aren't
Never email your demands: you can't control tone

Why product people lose

Introverted, thoughtful types (PMs, engineers, designers) negotiate significantly worse than sales and marketing types. The same people who built the tech generation consistently leave the most money on the table.

The $1B+ lesson

Jacob has negotiated against several of Lenny's podcast guests, unbeknownst to them. The gap between what companies offer and what they'll pay is almost always wider than you think.

Playbook

Tactics That Actually Move Numbers

Never negotiate by email, you lose control of tone. A CEO reading your email demands at airport security will misread the room entirely
Let them speak first on comp, anchor information flows both ways
Be collaborative, not adversarial, frame it as "helping them understand the value" not "fighting for more"
Push back on bands, those who challenge authority in a meaningful, collaborative way win more than those who don't
Ask specifically, "what's the chance there could be a little more" beats any aggressive opener

The fear reframe

Most people think: "I'll seem greedy." The reality: when you look at what the company is making vs. what you're asking, you're not being greedy. It doesn't have to be confrontational.

Jacob's real principle

These companies have significant leverage over you, they know what others make, what they'll accept. Your only equalizer is deeply understanding the value you create.

Mindset

What Great Negotiators Know

Never be so sure of your worth that you wouldn't accept more (Jacob's favorite Chris Voss line)
Haste equals risk. Slow the process down so you can collect the information that builds your case
Negotiation comes down to information and timing, that's what creates power
Under promise, over deliver. Always
The first offer is rarely the real offer

"If you understand the value you can create, you can have that conversation with confidence."

Contrarian

Comp Negotiation Myths

✗Negotiating makes you look greedyINSTEAD →✓ One simple question ("is there a little more?") delivers 20% in almost every case. Not greedy, expected.

✗Salary bands are fixed limitsINSTEAD →✓ Bands are treated as gospel but they're not. Those who challenge them with value evidence consistently break through.

✗Email is fine for comp discussionsINSTEAD →✓ Never negotiate by email. A CEO reading your demands while stressed misreads everything. Tone is everything, use your voice.

✗Smart people are good at negotiatingINSTEAD →✓ PMs, engineers, and designers, who built the tech generation, are systematically the worst negotiators. Introversion costs money.