Customers who pay annually in advance are funding customers who pay monthly in arrears. That feels off.

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Annual customers give us cash we invest in product development, support infrastructure, and operational improvements. Monthly customers benefit from those investments while paying only for the current month. The annual customers are essentially providing interest-free loans that subsidize the experience for monthly customers.

The annual discount we offer (two months free) doesn't fully compensate for the financial contribution annual customers make to the business's ability to invest. At our size the cash flow from annual prepayments is what makes hiring possible, infrastructure improvements fundable, and growth investable. Monthly customers consume these benefits without contributing to the capital that makes them possible.

I'm not going to change the pricing model over this observation. But it's made me think about whether annual customers deserve something beyond a price discount. Priority support, early access to features, a dedicated check-in cadence. Something that acknowledges the disproportionate financial contribution they make to the business's ability to improve.