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Depends on the role. For a Manager…one, maybe two, exchanges. For a VP and above position…exchanges can go on for a while.
If you're not happy with the compensation and you're not willing to work for that rate, I would just negotiate until they rescind the offer if you're not willing to take it for what they're willing to pay. If you really want the job, I would probably only do one more counter offer and that's it. But that's just me personally, I'm sure other people have different perspectives.
It really depends on tone and timing more than the number of rounds. A good-faith negotiation doesn’t make you a pain; it shows you value yourself. If they come back with $105k, you can go one more round, especially if you have a clear reason. A friend of mine responded with, “Would you be open to $110k to better reflect the scope and experience I bring?” and got it.
Generally, one or two rounds of negotiation is totally normal. After that, you start walking the fine line between standing your ground and being seen as difficult. If they go from $100k to $105k, that’s a pretty decent jump already. Personally, I’d only go back if you feel really strongly about the difference and have solid reasons for it. Otherwise, I’d be inclined to accept the $105k and appreciate the flexibility.
In this job market? I'd be nervous to push the envelope in the first place. It's one thing to know your worth, but another to know there are a hundred others after the same position. For me it depends on how much you need the job and if you're okay with them pulling the offer altogether. I also have never made that much money before in my life, so things might be different at that level lol.