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

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

Lenny's Podcast: Product | Career | Growth

Mar 15
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

Mar 15
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 [https://www.orkes.io/]—The enterprise platform for reliable applications and agentic workflows Mercury [https://mercury.com/?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q1_brand_campaign]—Radically different banking Omni [https://omni.co/lenny]—AI analytics your customers can trust — Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp [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 [https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0] — Where to find Jacob Warwick: • Substack: https://www.execsandthecity.com [https://www.execsandthecity.com] • YouTube: https://www.youtube.com/@ExecsandtheCity [https://www.youtube.com/@ExecsandtheCity] • Website: https://www.thinkwarwick.com [https://www.thinkwarwick.com] • Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course [https://www.execsandthecity.com/p/complete-job-search-course] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 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: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating [https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating] • Sam Altman on X: https://x.com/sama [https://x.com/sama] • Tom Brady on X: https://x.com/TomBrady [https://x.com/TomBrady] • Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8 [https://www.youtube.com/watch?v=TgjWTiSj8E8] • Salesforce: https://www.salesforce.com [https://www.salesforce.com] • Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts [https://en.wikipedia.org/wiki/Julia_Roberts] • Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon [https://en.wikipedia.org/wiki/Matt_Damon] • Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg [https://en.wikipedia.org/wiki/Steven_Spielberg] • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom [https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom] • Chris Voss’s quote: 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] • Chris Voss on X: https://x.com/fbinegotiator [https://x.com/fbinegotiator] • Werewolf: https://playwerewolf.co [https://playwerewolf.co] • Modes of persuasion: https://en.wikipedia.org/wiki/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 [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 [https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation] • Marvel: https://www.marvel.com [https://www.marvel.com] • Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030 [https://www.buzzsprout.com/2227030] • Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0 [https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0] • Minuscule: https://www.youtube.com/user/Minuscule [https://www.youtube.com/user/Minuscule] • Claude Cowork: https://claude.com/product/cowork [https://claude.com/product/cowork] • Macrofactor: https://macrofactor.com [https://macrofactor.com] • Whoop: https://www.whoop.com [https://www.whoop.com] • Gemini: https://gemini.google.com/app [https://gemini.google.com/app] • The Cody Dieruf Foundation: https://breathinisbelievin.org [https://breathinisbelievin.org] • Cystic Fibrosis Foundation: https://www.cff.org [https://www.cff.org] — Recommended books: • Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941 [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 [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 [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 [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 [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 [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/0671027034 [https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]

Highlights

In this episode, executive negotiation coach Jacob Warwick demystifies compensation negotiation—not as a zero-sum confrontation, but as a collaborative, value-driven process rooted in psychology, timing, and strategic communication.
00:00
Jacob Warwick has helped clients secure over $1 billion in additional comp
04:12
A simple pushback can yield a 20% increase in compensation
07:52
Companies usually extract much more value from employees than they pay in compensation
09:46
Negotiation is not adversarial—it's a collaborative tool to attract and retain top talent
13:03
Recent cases show over $10 million in compensation increases for a small team at a Fortune 500 company
18:32
Talking to recruiters is like a game of telephone—go straight to those controlling PNL and EBITDA
19:30
Use the 'home field advantage' by choosing a comfortable location and time for the negotiation conversation, which can show scarcity and make you more attractive
28:00
Settling for $1 million after asking for $1.3 million showed the negotiators weren't aggressive enough to find the ceiling
30:17
They find it difficult to negotiate with toddlers and mention bribing them
34:44
Negotiated a salary increase from $14 an hour to $120,000 a year in a month
38:06
Never share current compensation figures during negotiations
45:13
Working with Jacob Warwick makes it more likely to push back effectively on offers
45:45
The key approach is to figure out what matters to the other party, identify their problems, and help them visualize the benefits of having those problems solved.
47:20
Instead of relying on past achievements, they focused on the future
54:57
Ask about gaps, show problem-solving abilities, and slow down the hiring process to understand deeper company problems
59:02
Job search is reframed as a value-driven sales process where professionals apply enterprise sales principles to understand buyer needs and eliminate friction.
1:01:06
Position yourself like a product by understanding employer pain points through user research and showing how you solve them
1:05:11
Starting early in the process can create leverage to increase compensation from the standard 20% to 40% or more
1:11:16
Executives who understand P&L and how to influence rules should negotiate—because the rules are not set in stone
1:20:14
Negotiating in person or via video call is better than email because it enables reading body language, tone, and the ability to reschedule if the other person is not in a good state
1:24:23
Taking extreme ownership when things go wrong or when failing to deliver is essential
1:27:39
They convinced the CEO and CPO to advocate against Private Equity, resulting in retention and severance bonuses
1:31:20
Life outcomes aren't set—challenging clients' notions about money and retirement
1:32:55
An apology from an A-list celebrity saved a million dollars in a Hollywood franchise negotiation
1:37:35
Studies show those who anchor higher in compensation negotiations win more
1:40:30
Jacob's mission is to make insights from successful people accessible without gatekeeping—rooted in his lived experience with trauma and commitment to safety in negotiation
1:50:08
The Cody Dieruf Foundation funded a life-saving lung transplant for a child with cystic fibrosis

Chapters

Introduction to Jacob Warwick
00:00
How much comp people leave on the table
04:12
Why you shouldn’t feel greedy asking for more
07:52
What founders should know about negotiation
09:45
How Jacob works behind the scenes
13:03
The biggest mistakes people make when negotiating
15:35
Home-field advantage and controlling the conversation
19:30
The step-by-step approach to negotiating an offer
23:02
Jacob’s passion and why these tips don’t work on kids
30:17
Who should speak first about compensation
32:04
Understanding power
35:36
Breaking out of salary bands by focusing on pain points
39:52
Brief summary
45:45
Selling the vacation: How to visualize success
47:20
Controlling the narrative and planting seeds
50:07
Jacob’s role as hype man
59:01
Positioning yourself like a product
1:01:05
Making the process frictionless for hiring managers
1:02:49
Flipping the interview to extract information
1:06:20
Five tactical tips for negotiating comp
1:12:17
What to do when negotiations fall apart
1:21:45
Why negotiation is different for every individual
1:25:05
Why outcomes aren’t predetermined
1:28:55
Wild Hollywood negotiation stories
1:32:52
The first step you should take after getting an offer
1:37:35
Jacob’s personal mission
1:40:30
Lightning round and final thoughts
1:44:42

Transcript

Speaker 1: What's the most common mistake that people make when they're negotiating their comp? Speaker 2: Often, we'll hide behind the easiest communication channel possible. I might email you my demands. The problem with that is I can't control tone. If...