Employer Benefits Audit Before Retiring

What gets left on the table when people retire? More than you’d think, because some employer benefits are worth real money and they expire the day you leave, and nobody in HR is going to chase you to claim them. The fix is a deliberate sweep in your final year. Here’s the checklist.

Compensation you’ve earned but haven’t collected

• Unvested equity. Check whether stock options and RSUs forfeit at retirement or keep vesting. A single quarter can be worth six figures.
• Vested option exercise windows. Some expire as little as 90 days after you leave. Know the deadline before you set one.
• Deferred compensation. Confirm your payout election is the one you want, because it’s hard to change later.
• Unused PTO, sabbatical, and bonus eligibility. Find out what pays out and when, since the timing can stack income into a high-tax year.
• The pension, if you have one. Get the lump-sum-versus-monthly figures in writing, see pension lump sum vs. monthly.

Health and insurance, the expiring kind

• Retiree medical, if your employer offers it. Increasingly rare and valuable if it exists.
• Your HSA. Max it before you go, and know it stays yours after you leave.
• COBRA terms as a possible short bridge, see COBRA vs. marketplace coverage.
• Group life and disability. Some policies let you convert to an individual plan, though for most people the coverage need is shrinking, so don’t convert on autopilot.

The fine print that’s quietly worth a lot

• Employer 401(k) match. Make sure you capture the full match in your final year before contributions stop.
• Net unrealized appreciation. If your 401(k) holds appreciated company stock, the NUA rules can sharply cut the tax, but only if you handle the rollover correctly. This one is easy to fumble and expensive to get wrong.
• Stock purchase plan shares, and their cost basis.

The part most people miss

Most people treat the exit as an HR formality, sign here, hand in the badge. The second-order cost is that these benefits don’t just disappear, they convert into tax decisions that follow you for years. A mishandled NUA rollover, a deferred-comp payout that lands in your top bracket, an option window you let lapse, each one quietly raises your lifetime tax bill or simply forfeits money you earned. Do the audit a full year out, not the week you leave. The benefits you claim on the way out the door fund the life you’re walking into.