Most software-as-a-service (SaaS) products utilize monthly billing but often offer discounts for annual or biennial upfront commitments, providing benefits such as reduced customer churn and improved cash flow. For example, Optimizely and Olark offer 10% off for a one-year commitment, increasing the discount for two years. An upfront contract secures more guaranteed revenue and encourages stronger customer engagement. Analyzing churn rates helps determine the optimal discount, as in the case of a 3% monthly churn indicating a viable 15% annual discount. Upfront payments bolster cash flow, allowing for reinvestment in growth, exemplified by a hypothetical scenario showing that offering significant discounts can lead to substantial customer base expansion. SaaS companies employ various strategies for billing, including mandatory long-term contracts or hybrid models with optional upfront payment incentives, depending on their customer acquisition costs and business objectives. Overall, upfront billing reduces churn, enhances cash flow, and offers additional advantages like decreased billing uncertainty and transaction costs, making it a strategy worth encouraging for SaaS businesses.