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

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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% bump2. Why Jacob sees 40% average movement when negotiations are run well3. When negotiation actually starts (hint: it’s much earlier than you think)4. Why information + timing create power5. The biggest mistakes people make when negotiating6. How to navigate the important “What’s your comp expectation?” question without anchoring too low7. Why the best interviews feel more like discovery calls than interrogations—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflowsMercury—Radically different bankingOmni—AI analytics your customers can trust—Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—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—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.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 be