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It's one of the big reasons why I try to finalize contracts before announcing a round of funding. You'd be amazed at how much pricing for things jumps immediately after announcing that Series B.

Yes, that happens.

Sometimes it is also possible to brand the exact same service in different ways.

If you have a SaaS that is fully OSHA compliant on all tiers, it may be worth it to not mention the OSHA compliance on lower tiers, but only offer it on the Enterprise tier for example.

Sure, why not? Or they impute value from usage.

Cost based on usage seems very fair to me, but GP said "rich users pay more, poor users pay less," which seems to suggest that if Microsoft emailed me asking about a SaaS subscription for 1M req/day, I should quote them orders of magnitude more than a small startup asking for the same 1M req/day.