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Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

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

Mar 15, 2026 · 1h 55m

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On this episode

About this episode

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.…