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Comment on Ask HN: When did people start paying for your SaaS and why?parent

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I recommend aiming a little lower. Companies with 500 employees and HR departments already have a lot of structure and process around making purchases. There are lots of much smaller companies with lots of revenue and very large pain points that you could easily solve for them. It is much easier to talk directly to the decision makers of these companies and if you treat them well they will be your biggest fans.

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