Should You Even Stay?

You won’t hear anyone ask it at the all-hands. It gets asked later, at eleven at night with a job site open on your phone, or in a text to the coworker who left last year. Out loud it can sound disloyal, so it tends to get worked out alone, on rumors about which teams the buyer already has.

It is a career question. Inside a deal it’s a money question too, often one of the biggest you’ll face, and the rules for it are already written, in your award agreements and in any severance plan or retention letter you’ve signed. You probably haven’t reread any of them since the day they arrived.

Whatever hasn’t vested is usually forfeited when you resign, including grants the buyer just converted into its own. If you hold vested options, leaving can also start a clock to exercise them, sometimes a short one. And a retention bonus, if you were offered one, usually comes with a date attached. Leave before it and you may lose the bonus, or owe back money you were already paid.

Some award agreements and severance plans, especially at senior levels, protect people who are let go without cause during a set window around the deal, often with faster vesting, severance pay, or both. Resigning on your own usually doesn’t qualify. If your documents work that way, quitting a few weeks before a layoff could cost you what the layoff would have paid. Nobody can promise you a layoff is coming, and waiting for one has its own costs. I’d just rather you learn which side of that line you’re on from your own documents than from HR on your way out.

Those protections often cover leaving for what the documents call good reason, which is narrower than it sounds. It usually means something specific and serious, like a real cut in pay or a much smaller job, and it often runs on a clock. You may have to give written notice within a set number of days and give the company time to fix the problem before you resign. Miss a step and the protection can be gone. Read anything new you’re asked to sign around the deal just as closely, because some of those agreements ask you to give up good reason over the very changes the deal brings.

With all of that on paper, both choices have a price. Staying is worth whatever keeps vesting, plus any retention money and the protection you’d keep if your role gets cut inside the window. Going costs what you’d forfeit and anything you’d owe back, and a new offer has to cover that before its salary even starts to count. A new employer may offer to replace some of what you’d leave behind, and it can only price what you can show it.

None of this is a vote for staying. Leaving can be exactly the right call, and so can staying. The money side just deserves its own look, with the documents open and the dates in front of you, before the career side decides for you.

You don’t have to ask this question at the all-hands. Just don’t answer it alone at eleven at night.

This is the third letter in a short series on what a deal does to your money. Friday is about the people in the building who know the most about your deal, and why they usually can’t tell you what to do about it.

Talk Friday.

Mateo

P.S. If your company is in the middle of a deal right now, there’s a deal checklist at bfawealth.com/deals.