👋🏻 Jacob here.
Let’s talk about a handy tool that you should be using in your executive compensation that’s hiding in plain sight:
Milestone payments.
Most execs are stuck in the base salary + bonus + equity loop. And leaning on objective benchmark data to settle for something loosely attached to mediocrity.
But the real ballers? They’re playing a different game entirely.
Here’s the deal:
Milestone payments are like performance bonuses on steroids. They’re big, chunky payouts tied to specific achievements.
And, in my not-so-humble opinion, they’re the most underrated and low-risk form of executive compensation.
Picture this:
You’re negotiating to be head of growth at a hot startup. Instead of settling for vague equity promises, you say:
“Cut me $500k when we hit $10M ARR, $1M at $25M, and $2M at $50M.”
Or you’re a CFO steering towards an IPO. You tell the board:
“I’m up for the challenge, but I want $1M when we ring that bell on Wall Street.”
Why do milestone payments work? Let me break it down:
- Zero risk for the company. No milestones, no moolah.
- It doesn’t mess with the cap table. Other execs can’t cry about equity dilution.
- Win-win. If they’re cutting you a fat check, you’ve crushed it for them too.
Real talk: I’ve seen too many execs get screwed by worthless options or “long-term incentives” that never materialize.
Milestone payments? They put cold, hard cash in your pocket when you deliver.
I recently used this to turn a $700k/year CRO opportunity into a nearly $3.5M/year offer for a client.
How? By channeling a little Tom Brady energy (and what I learned negotiating in Hollywood deals).
When the GOAT won his Tampa Bay Super Bowl, he didn’t just get a ring. He triggered:
- $750k for a wild card win
- $1.25M for winning the NFC Championship
- $1.75M for reaching the Super Bowl
- $2.25M success bonus for winning it all
That’s how the big ballers play.
Is it greedy? Hell no.
You know what’s greedy? Companies expect top-tier talent to turn water into wine without putting real skin in the game.
Here’s the bottom line:
If you’re not asking for milestone payments, you’re leaving millions on the table.
Next time you’re at the negotiating table, throw this curveball.
Watch how quickly they realize you’re not just another exec. You’re a game-changer who knows their worth.
Remember: In the C-suite, if you’re not asking, you’re not getting.
Stay fearless, friends.
See you next week.