Uploaded March 2026 | Updated September 2026, 1 week ago
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: orkes.io
Mercury—Radically different banking: mercury.com
Omni—AI analytics your customers can trust: omni.co/lenny
*Episode transcript:* lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp
*Archive of all Lenny's Podcast transcripts:* dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
*Where to find Jacob Warwick:*
• Substack: execsandthecity.com
• YouTube: youtube.com/@jacob-warwick
• Website: thinkwarwick.com
• Complete Job Search Course: execsandthecity.com/p/complete-job-search-course
*Where to find Lenny:*
• Newsletter: lennysnewsletter.com
• X: twitter.com/lennysan
• LinkedIn: linkedin.com/in/lennyrachitsky
*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
*Referenced:*
• The ultimate guide to negotiating your comp: 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: youtube.com/watch?v=TgjWTiSj8E8
• Salesforce: salesforce.com
• Julia Roberts: en.wikipedia.org/wiki/Julia_Roberts
• Matt Damon: en.wikipedia.org/wiki/Matt_Damon
• Steven Spielberg: en.wikipedia.org/wiki/Steven_Spielberg
• Marc Andreessen: The real AI boom hasn’t even started yet: lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
• Chris Voss’s quote: goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that
• Chris Voss on X: https://x.com/fbinegotiator
• Werewolf: playwerewolf.co
• Modes of persuasion: en.wikipedia.org/wiki/Modes_of_persuasion
• How to use tactical empathy: linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy
• ZOPA, BATNA and Win-Win in Negotiation: parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation
...References continued at: lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp
_Production and marketing by penname.co/._
_For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._
Lenny may be an investor in the companies discussed.
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: orkes.io
Mercury—Radically different banking: mercury.com
Omni—AI analytics your customers can trust: omni.co/lenny
*Episode transcript:* lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp
*Archive of all Lenny's Podcast transcripts:* dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
*Where to find Jacob Warwick:*
• Substack: execsandthecity.com
• YouTube: youtube.com/@jacob-warwick
• Website: thinkwarwick.com
• Complete Job Search Course: execsandthecity.com/p/complete-job-search-course
*Where to find Lenny:*
• Newsletter: lennysnewsletter.com
• X: twitter.com/lennysan
• LinkedIn: linkedin.com/in/lennyrachitsky
*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
*Referenced:*
• The ultimate guide to negotiating your comp: 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: youtube.com/watch?v=TgjWTiSj8E8
• Salesforce: salesforce.com
• Julia Roberts: en.wikipedia.org/wiki/Julia_Roberts
• Matt Damon: en.wikipedia.org/wiki/Matt_Damon
• Steven Spielberg: en.wikipedia.org/wiki/Steven_Spielberg
• Marc Andreessen: The real AI boom hasn’t even started yet: lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
• Chris Voss’s quote: goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that
• Chris Voss on X: https://x.com/fbinegotiator
• Werewolf: playwerewolf.co
• Modes of persuasion: en.wikipedia.org/wiki/Modes_of_persuasion
• How to use tactical empathy: linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy
• ZOPA, BATNA and Win-Win in Negotiation: parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation
...References continued at: lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp
_Production and marketing by penname.co/._
_For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._
Lenny may be an investor in the companies discussed.
