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

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Mar 15, 2026

Guest

Jacob Warwick

Jacob Warwick, an executive negotiation coach and former founder, shares a sharper way to ask for more without sounding pushy. They get into why negotiation starts long before the offer, how to dodge the comp expectations trap, why interviews should feel like discovery calls, and the subtle language that can unlock surprisingly big moves.

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insights

INSIGHT

Control The Narrative Before Others Repeat It

Elite operators shape what others will later say about them by planting language and asking for live feedback.
Jacob Warwick prompts references, interviewers, and even podcast audiences with the narrative he wants repeated.

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ADVICE

Use Your Existing Craft To Negotiate Better

Build confidence by translating negotiation into a discipline you already know instead of mimicking someone else's style.
Jacob Warwick tells product people to treat a job search like product work: identify users, remove friction, and design for buyer needs.

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ADVICE

Make The Hiring Process Frictionless For Them

Make the hiring process cognitively easy by leading interviews, predicting next stakeholders, and asking to be coached for each conversation.
Jacob Warwick says this builds internal champions, surfaces hidden needs, and creates leverage before comp talks start.

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Why Most People Undersell Themselves

04:16 • 6min

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Why Founders Should Welcome Negotiation

09:49 • 6min

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Negotiation Starts Before The Offer

15:36 • 7min

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How To Respond To An Offer

22:24 • 10min

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Handling The Compensation Expectation Trap

32:04 • 8min

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Sell Pain Relief, Not Your Resume

39:54 • 7min

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Selling The Vacation In Interviews

46:45 • 9min

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Position Yourself Like A Product

Make Hiring You Feel Effortless

59:03 • 7min

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Using Questions To Expose Value Gaps

01:06:22 • 6min

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Five Rules For Better Negotiations

01:12:20 • 9min

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What To Do When Things Break Down

01:21:46 • 7min

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Why No Outcome Is Predetermined

01:28:57 • 6min

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Wild Lessons From Hollywood Deals

01:35:08 • 2min

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Your First Move After The Offer

01:37:36 • 3min

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The Mission Behind Jacob’s Work

01:40:31 • 4min

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Lightning Round And Closing Reflections

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Negotiation Made Simple offers a practical, systematic approach to negotiation developed by John Lowry, who has trained thousands of professionals across the United States. Leveraging his background as a lawyer, consultant, and coach, Lowry provides actionable strategies taught at leading institutions like Pepperdine University. The book emphasizes effective techniques for real-world results in business and personal negotiations.

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

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