My opinion as someone who is running a SaaS business: - Annual contracts are better than month-to-month, because you will get a customer for a year in most cases, extending your LTV - Customer choose annual not only for the pricing discount but speaks to their commitment with your solution. I take it as a great product market fit indicator. - Your price should be aligned with your competition. You can increase prices for new users but don't increase the price for your existing pay customers. - Offer your monthly customers the option to upgrade to annual as well