Are retention bonuses ever worth it? The money sounds nice ($50K for 2 years) but I'm afraid of getting stuck and missing out on getting an offer that would be better long term.

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Ha, 50k for a retention bonus ... is this a bad joke, we don't even get pizza.

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That sounds like a trap. If you get fired you probably don’t get the bonus. Only worth it if you get 25k per year paid out

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Normally, you get a retention bonus up front and sign a contract that you will pay it back if you leave voluntarily before the agreed upon date.

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Our company does this for senior level staff and high performers. Ours is a 10 year lock in. I would take a 2 year arrangement at $50k immediately. 2 years isn’t very long. You should endeavor to stay at an employer for 2 years anyway.

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I wish they would offer me a retention bonus

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Retention bonus ?

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Depends on what your plans are and the terms of the contract. I had a 5 year and they laid me off on year 4. But, since it was for unjust cause, they still had to pay everything out to me.
I included it as part of yearly salary, so any offer would have to be higher than salary plus bonus to even think about moving. Even negotiating additional retention bonus for other offers. Just share generalities of the contract during the interview process.
If you make yourself desirable, others will believe so.

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Sounds like Amazon. I've heard they do stuff like that.

It’s worth it. If you decide to leave you could always let your new employer know you want them to pay it as a sign on for you to pay it back to your other employer.

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