The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
3/15/20261 hr 55 min
Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.
We discuss:
1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump
2. Why Jacob sees 40% average movement when negotiations are run well
3. When negotiation actually starts (hint: it’s much earlier than you think)
4. Why information + timing create power
5. The biggest mistakes people make when negotiating
6. How to navigate the important “What’s your comp expectation?” question without anchoring too low
7. Why the best interviews feel more like discovery calls than interrogations
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Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Jacob Warwick:
• Substack: https://www.execsandthecity.com
• YouTube: https://www.youtube.com/@ExecsandtheCity
• Website: https://www.thinkwarwick.com
• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Jacob Warwick
(04:12) How much comp people leave on the table
(07:52) Why you shouldn’t feel greedy asking for more
(09:45) What founders should know about negotiation
(13:03) How Jacob works behind the scenes
(15:35) The biggest mistakes people make when negotiating
(19:30) Home-field advantage and controlling the conversation
(23:02) The step-by-step approach to negotiating an offer
(30:17) Jacob’s passion and why these tips don’t work on kids
(32:04) Who should speak first about compensation
(35:36) Understanding power
(39:52) Breaking out of salary bands by focusing on pain points
(45:45) Brief summary
(47:20) Selling the vacation: How to visualize success
(50:07) Controlling the narrative and planting seeds
(59:01) Jacob’s role as hype man
(01:01:05) Positioning yourself like a product
(01:02:49) Making the process frictionless for hiring managers
(01:06:20) Flipping the interview to extract information
(01:12:17) Five tactical tips for negotiating comp
(01:21:45) What to do when negotiations fall apart
(01:25:05) Why negotiation is different for every individual
(01:28:55) Why outcomes aren’t predetermined
(01:32:52) Wild Hollywood negotiation stories
(01:37:35) The first step you should take after getting an offer
(01:40:30) Jacob’s personal mission
(01:44:42) Lightning round and final thoughts
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Referenced:
• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating
• Sam Altman on X: https://x.com/sama
• Tom Brady on X: https://x.com/TomBrady
• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8
• Salesforce: https://www.salesforce.com
• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts
• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon
• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg
• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that
• Chris Voss on X: https://x.com/fbinegotiator
• Werewolf: https://playwerewolf.co
• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion
• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy
• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation
• Marvel: https://www.marvel.com
• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030
• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0
• Minuscule: https://www.youtube.com/user/Minuscule
• Claude Cowork: https://claude.com/product/cowork
• Macrofactor: https://macrofactor.com
• Whoop: https://www.whoop.com
• Gemini: https://gemini.google.com/app
• The Cody Dieruf Foundation: https://breathinisbelievin.org
• Cystic Fibrosis Foundation: https://www.cff.org
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Recommended books:
• Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941
• Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X
• You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229
• Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
Clips
Transcript preview
First 90 secondsLenny Rachitsky· Host0:00
What's the most common mistake that people make when they're negotiating their comp?
Jacob Warwick· Guest0:03
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."
Lenny Rachitsky· Host0:18
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."
Jacob Warwick· Guest0:24
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.
Lenny Rachitsky· Host0:37
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."
Jacob Warwick· Guest0:44
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.
Lenny Rachitsky· Host0:56
[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