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The same way you would when employed by any other type of business.

There are certainly similarities, but I feel that with a startup there are some different expectations. For example since I get (a small amount of) stock options, and it is a small company it would not have a large amount of cash stored in the bank the counterargument to me asking for a raise might just be "we are already paying you enough and we cannot afford any more".

The other distinction is that we have no dedicated HR staff so I'll be negotiating directly with the CFO.

Since you are probably not privy to your employers actual financials, there is no point speculating.

Just go ahead and ask. If they tell you there's no money, or that they think they're already paying you enough, try to negotiate a re-evaluation in 3 to 6 months.

Decide for yourself if you can live with not getting a raise. Negotiating directly with the CFO beats negotiating with him through an HR person.

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