Original: Lenny Rachitsky · 15/03/2026
Summary
Jacob Warwick shares strategies for negotiating better compensation, emphasizing collaboration and timing to achieve significant salary increases.Key Insights
“Whats the chance theres a little more here?” — A simple question that can unlock a 20% bump in salary negotiations.
“When negotiation actually starts (hint: its much earlier than you think)” — Highlighting the importance of early engagement in the negotiation process.
“The biggest mistakes people make when negotiating” — Discussing common pitfalls in negotiation that can hinder success.
Topics
Full Article
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.Listen on YouTube, Spotify, and Apple PodcastsWe discuss:Why a simple Whats the chance theres a little more here? often unlocks a 20% bumpWhy Jacob sees 40% average movement when negotiations are run wellWhen negotiation actually starts (hint: its much earlier than you think)Why information + timing create powerThe biggest mistakes people make when negotiatingHow to navigate the important Whats your comp expectation? question without anchoring too lowWhy the best interviews feel more like discovery calls than interrogationsBrought to you by:OrkesThe enterprise platform for reliable applications and agentic workflowsMercuryRadically different bankingOmniAI analytics your customers can trustWhere 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-courseReferenced: 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 hasnt even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom Chris Vosss 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.orgRecommended 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/0671027034Production 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: Read moreRelated Articles
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Originally published at https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp.