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I'm all for doing what you can to up your pay because, at the end of the day, that's the only concrete way a company can show that it values you.

However, quaterly seems a bit extreme to the point of being nagging/needy. Consider how your relationship with someone changes if they kept asking the same question. I would think at some point you would become the "ugh, he's asking for a raise again" guy. So the worst case isn't a NO. The worst case is you get filed as "that guy".

Maybe space it out while asking for bigger ones?

How many times have you asked for a raise with this schedule?

As someone who runs a small company, I agree with this 100%. You don't want to be that guy.

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