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

Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Mercury—Radically different banking

Omni—AI analytics your customers can trust

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

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

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

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:...