Why You’re Getting Screwed in Job Offers (And How to Fix It)

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👋🏻 Jacob here.

If you’re like most executives — you’re getting screwed in your job negotiations.

Let’s talk about the elephant in the room that many win-win negotiators don’t notice: information asymmetry in job offer negotiations.

You think you’re playing chess, but the employer’s playing 4D chess while you’re still setting up the board.

Here’s the truth:

  • The employer knows their budget, internal equity, and market rates. You’re left guessing.
  • They’ve done this dance hundreds of times. You do it every few years, if that.
  • They have a team of HR pros and lawyers. You have… Google?
  • They know exactly how much wiggle room they have. You’re shooting in the dark.

Wake-up call: This isn’t a fair fight. And it’s not even close. It’s a setup for a win-lose negotiation.

Real negotiation power isn’t about fancy tactics or “power moves.”

It’s about:

  • Understanding the full scope of what’s on the table (hint: it’s more than just base salary)
  • Knowing the company’s pain points and how valuable it is for you to solve them
  • Having multiple offers to create leverage
  • Being willing to walk away (and meaning it)
  • Mastering the art of silence in crucial moments
  • Building rapport with the entire ELT and investors, not just HR
  • Crafting a compelling narrative about your value

Oh, and remember – timing is everything.

Bring up money too soon? Game over. Too late? You’ve lost your leverage.

Are you missing these key points?

  • Overly focused on “What’s your salary expectation?” 
  • Struggling to articulate your unique value proposition?

You’re likely getting lowballed—even if you think you’re winning. You’re exposed.

Asymmetrical negotiations will devastate your career earnings. They stroke your ego with a small win now but kneecap your earning potential for years to come.

Don’t settle for table scraps—learn how to create real compensation alignment.

Remember: Information is power. The more you know, the stronger your position.

Be strategic about what you share and when. It’s your best shot at leveling the playing field.

I’m producing a masterclass course soon. Message me if you want to get notified of the progress. In the meantime, read the #negotiation section on the Execs and the City blog for free help.


Stay fearless, friends.

See you next week.

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