The Executive Exit: Your Stock Options Game Plan Before Changing Jobs

Oct 18

Switching jobs? Great.
But before you update your LinkedIn headline, remember this: your equity doesn’t resign when you do — it just quietly starts expiring.

Leaving a job with stock options or RSUs isn’t a clean break; it’s a high-stakes, fine-print chess match between your next opportunity and your unvested future.

Step 1: Read the Rules Before You Play

Every equity plan has its own DNA — and most employees never read it until it’s too late.

Before you tell your manager you’re moving on, quietly collect:

Your grant agreements (each one, not just the summary)
Vesting schedules and expiration dates
The fine print on post-termination exercise (PTE) periods

Because once you hand in that badge, the countdown begins.
Most ISOs expire in 90 days. RSUs stop vesting immediately. And performance shares? They might just evaporate in the HR portal.

Step 2: Know What’s at Stake (Literally)

Run the math:

Intrinsic Value: (Market Price – Strike Price) × Shares
Tax Reality: Ordinary income for NSOs; possible AMT for ISOs
Liquidity Plan: Can you afford to exercise — and should you?

Executives often focus on base salary, yet a single mis-timed exercise can cost more than an entire year’s pay.
This isn’t trivia — it’s the real compensation conversation.

Step 3: Negotiate Vesting Like You Negotiate Salary

This is the most overlooked power move in executive transitions.

If you’re walking away from unvested stock, make it part of the negotiation.
Smart candidates ask:

“Can we accelerate vesting for upcoming RSUs?”
“Will there be a make-whole grant to replace forfeited equity?”
“Can vesting be tied to the start date instead of calendar year?”

Frame it like a fiduciary, not a favor:

“I want to make this transition seamless — both for my focus and for continuity. Adjusting vesting alignment makes that possible.”

Employers expect this conversation at your level. It’s the sign of someone who understands the true economics of a career move.

Step 4: Decide When to Exercise — Before or After You Leave

Timing is a tax play, not a guessing game.

Before leaving:
You may preserve ISO status and exercise under more predictable conditions.
After leaving:
You might gain flexibility if your company allows extended PTE windows — but that’s rare.

And if you’re at a private company, confirm liquidity options before you sign any exercise check. Nothing says “career regret” like owning six figures of stock in a firm that may never IPO.

Step 5: Treat the Exit as a Liquidity Event

Once the dust settles, your job change becomes your rebalancing moment.
Sell some shares. Rebuild your allocation. Re-engineer your tax profile for the new income bracket.

The goal isn’t to time the next rally — it’s to convert career equity into portable wealth that funds your next chapter, not your former employer’s balance sheet.

Closing Thought

You worked for years to earn those options. Don’t let them vanish in a 90-day countdown you didn’t plan for.

Your career can pivot. Your equity shouldn’t disappear.

A little foresight — and a confident vesting conversation — can turn a resignation into a wealth event.

Disclosure

This post is for informational purposes only and does not constitute tax, legal, or investment advice. Always consult your tax professional or financial planner before acting on equity compensation decisions.

Kumbie Mtunga