<ul><li>Offer upfront cash for bigger deals, but be cautious with smaller ones and where it's not natural.</li><li>Collecting upfront for annual and multi-year contracts can provide immediate cash flow and customer commitment.</li><li>Offer discounts for upfront payments, but be careful not to sacrifice long-term revenue.</li><li>Cash upfront on larger deals is beneficial, but consider factors like collections, not overdoing it, and customer fit.</li></ul>

Dear SaaStr: How Hard Should We Push to Get Cash Upfront in Deals?

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