“we were mostly monthly for the first three years for a couple different reasons one we just didn't want the complexity of dealing with this but we wanted to have hard-earned retention where we were learning what is the correlation of behavior and membership to month one retention month two retention month three retention and having that masked in annual is really hard to use as a Guiding Light for the team”

Stay monthly until retention is proven; then introduce annual to compress payback

Most apps rush to annual plans to improve cash flow. Ladder deliberately stayed monthly for three years so that every retention signal was unmasked — a bad month-one retention figure was immediately visible and fixable, not buried under annual pre-payments. Only after achieving top-of-benchmark monthly retention did they introduce an annual option, taking their annual mix from 0% to 30% almost immediately with a simple side-by-side paywall tweak.