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

MAR 15, 2026114 MIN
Lenny's Podcast: Product | Career | Growth

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

MAR 15, 2026114 MIN

Description

<p><strong>Jacob Warwick</strong> 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.</p><p></p><p><strong>We discuss:</strong></p><p>1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump</p><p>2. Why Jacob sees 40% average movement when negotiations are run well</p><p>3. When negotiation actually starts (hint: it’s much earlier than you think)</p><p>4. Why information + timing create power</p><p>5. The biggest mistakes people make when negotiating</p><p>6. How to navigate the important “What’s your comp expectation?” question without anchoring too low</p><p>7. Why the best interviews feel more like discovery calls than interrogations</p><p>—</p><p><strong>Brought to you by:</strong></p><p><a target="_blank" href="https://www.orkes.io/"><strong>Orkes</strong></a>—The enterprise platform for reliable applications and agentic workflows</p><p><a target="_blank" href="https://mercury.com/?utm_source=lennys&#38;utm_medium=sponsored_newsletter&#38;utm_campaign=26q1_brand_campaign"><strong>Mercury</strong></a>—Radically different banking</p><p><a target="_blank" href="https://omni.co/lenny"><strong>Omni</strong></a>—AI analytics your customers can trust</p><p>—</p><p><strong>Episode transcript:</strong> <a target="_blank" href="https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp">https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp</a></p><p>—</p><p><strong>Archive of all Lenny's Podcast transcripts: </strong><a target="_blank" href="https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&#38;st=ahz0fj11&#38;dl=0">https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0</a></p><p>—</p><p><strong>Where to find Jacob Warwick:</strong></p><p>• Substack: <a target="_blank" href="https://www.execsandthecity.com">https://www.execsandthecity.com</a></p><p>• YouTube: <a target="_blank" href="https://www.youtube.com/@ExecsandtheCity">https://www.youtube.com/@ExecsandtheCity</a></p><p>• Website: <a target="_blank" href="https://www.thinkwarwick.com">https://www.thinkwarwick.com</a></p><p>• Complete Job Search Course: <a target="_blank" href="https://www.execsandthecity.com/p/complete-job-search-course">https://www.execsandthecity.com/p/complete-job-search-course</a></p><p>—</p><p><strong>Where to find Lenny:</strong></p><p>• Newsletter: <a target="_blank" href="https://www.lennysnewsletter.com">https://www.lennysnewsletter.com</a></p><p>• X: <a target="_blank" href="https://twitter.com/lennysan">https://twitter.com/lennysan</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com/in/lennyrachitsky/">https://www.linkedin.com/in/lennyrachitsky/</a></p><p>—</p><p><strong>In this episode, we cover:</strong></p><p>(00:00) Introduction to Jacob Warwick</p><p>(04:12) How much comp people leave on the table</p><p>(07:52) Why you shouldn’t feel greedy asking for more</p><p>(09:45) What founders should know about negotiation</p><p>(13:03) How Jacob works behind the scenes</p><p>(15:35) The biggest mistakes people make when negotiating</p><p>(19:30) Home-field advantage and controlling the conversation</p><p>(23:02) The step-by-step approach to negotiating an offer</p><p>(30:17) Jacob’s passion and why these tips don’t work on kids</p><p>(32:04) Who should speak first about compensation</p><p>(35:36) Understanding power</p><p>(39:52) Breaking out of salary bands by focusing on pain points</p><p>(45:45) Brief summary</p><p>(47:20) Selling the vacation: How to visualize success</p><p>(50:07) Controlling the narrative and planting seeds</p><p>(59:01) Jacob’s role as hype man</p><p>(01:01:05) Positioning yourself like a product</p><p>(01:02:49) Making the process frictionless for hiring managers</p><p>(01:06:20) Flipping the interview to extract information</p><p>(01:12:17) Five tactical tips for negotiating comp</p><p>(01:21:45) What to do when negotiations fall apart</p><p>(01:25:05) Why negotiation is different for every individual</p><p>(01:28:55) Why outcomes aren’t predetermined</p><p>(01:32:52) Wild Hollywood negotiation stories</p><p>(01:37:35) The first step you should take after getting an offer</p><p>(01:40:30) Jacob’s personal mission</p><p>(01:44:42) Lightning round and final thoughts</p><p>—</p><p><strong>Referenced:</strong></p><p>• The ultimate guide to negotiating your comp: <a target="_blank" href="https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating">https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating</a></p><p>• Sam Altman on X: <a target="_blank" href="https://x.com/sama">https://x.com/sama</a></p><p>• Tom Brady on X: <a target="_blank" href="https://x.com/TomBrady">https://x.com/TomBrady</a></p><p>• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: <a target="_blank" href="https://www.youtube.com/watch?v=TgjWTiSj8E8">https://www.youtube.com/watch?v=TgjWTiSj8E8</a></p><p>• Salesforce: <a target="_blank" href="https://www.salesforce.com">https://www.salesforce.com</a></p><p>• Julia Roberts: <a target="_blank" href="https://en.wikipedia.org/wiki/Julia_Roberts">https://en.wikipedia.org/wiki/Julia_Roberts</a></p><p>• Matt Damon: <a target="_blank" href="https://en.wikipedia.org/wiki/Matt_Damon">https://en.wikipedia.org/wiki/Matt_Damon</a></p><p>• Steven Spielberg: <a target="_blank" href="https://en.wikipedia.org/wiki/Steven_Spielberg">https://en.wikipedia.org/wiki/Steven_Spielberg</a></p><p>• Marc Andreessen: The real AI boom hasn’t even started yet: <a target="_blank" href="https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom">https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom</a></p><p>• Chris Voss’s quote: <a target="_blank" href="https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that">https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that</a></p><p>• Chris Voss on X: <a target="_blank" href="https://x.com/fbinegotiator">https://x.com/fbinegotiator</a></p><p>• Werewolf: <a target="_blank" href="https://playwerewolf.co">https://playwerewolf.co</a></p><p>• Modes of persuasion: <a target="_blank" href="https://en.wikipedia.org/wiki/Modes_of_persuasion">https://en.wikipedia.org/wiki/Modes_of_persuasion</a></p><p>• How to use tactical empathy: <a target="_blank" href="https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy">https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy</a></p><p>• ZOPA, BATNA and Win-Win in Negotiation: <a target="_blank" href="https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation">https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation</a></p><p>• Marvel: <a target="_blank" href="https://www.marvel.com">https://www.marvel.com</a></p><p>• Negotiation Made Simple podcast: <a target="_blank" href="https://www.buzzsprout.com/2227030">https://www.buzzsprout.com/2227030</a></p><p>• <em>Luca </em>on Disney+: <a target="_blank" href="https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0">https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0</a></p><p>• <em>Minuscule</em>: <a target="_blank" href="https://www.youtube.com/user/Minuscule">https://www.youtube.com/user/Minuscule</a></p><p>• Claude Cowork: <a target="_blank" href="https://claude.com/product/cowork">https://claude.com/product/cowork</a></p><p>• Macrofactor: <a target="_blank" href="https://macrofactor.com">https://macrofactor.com</a></p><p>• Whoop: <a target="_blank" href="https://www.whoop.com">https://www.whoop.com</a></p><p>• Gemini: <a target="_blank" href="https://gemini.google.com/app">https://gemini.google.com/app</a></p><p>• The Cody Dieruf Foundation: <a target="_blank" href="https://breathinisbelievin.org">https://breathinisbelievin.org</a></p><p>• Cystic Fibrosis Foundation: <a target="_blank" href="https://www.cff.org">https://www.cff.org</a></p><p>—</p><p><strong>Recommended books:</strong></p><p>• <em>Negotiation Games</em>: <a target="_blank" href="https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941">https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941</a></p><p>• <em>Influence: The Psychology of Persuasion</em>: <a target="_blank" href="https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X">https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X</a></p><p>• <em>You Can Negotiate Anything: How to Get What You Want</em>: <a target="_blank" href="https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229">https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229</a></p><p>• <em>Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal</em>: <a target="_blank" href="https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325">https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325</a></p><p>• <em>Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity</em>: <a target="_blank" href="https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509">https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509</a></p><p>• <em>High Output Management</em>: <a target="_blank" href="https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884">https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884</a></p><p>• <em>How to Win Friends and Influence People</em>: <a target="_blank" href="https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034">https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034</a></p><p>—</p><p>Production and marketing by <a target="_blank" href="https://penname.co/">https://penname.co/</a>. For inquiries about sponsoring the podcast, email <a target="_blank" href="mailto:[email protected]">[email protected]</a>.</p><p>—</p><p><em>Lenny may be an investor in the companies discussed.</em></p> <br/><br/>To hear more, visit <a href="https://www.lennysnewsletter.com?utm_medium=podcast&#38;utm_campaign=show-notes-no-free-preview-language">www.lennysnewsletter.com</a>