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Sarah Mitchell
Sarah Mitchell

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Annual billing looks cheaper. Here is the month it actually becomes cheaper.

Every SaaS checkout offers the same trade: pay for a year up front, get two months free. It reads as a discount. It is really a bet that you will still want the tool in month ten.

Here is the arithmetic I run before taking it.

Monthly cost = monthly price x seats
Annual cost = annual price x seats, paid on day one
Break-even = annual cost / monthly cost

If a tool is $50 a month or $500 a year for one seat, the annual deal costs ten months of the monthly plan. Month ten is where it turns into a saving. Cancel in month seven and you paid $500 for $350 of use.

Three things move that number and none of them are on the pricing page.

Seat minimums. If the plan sells in rungs of five and you need twelve people, you are buying fifteen, so the real crossover is later than the per-seat math suggests.

Add-ons that run out. Trial credit grants are the current favourite. A CRM can advertise thousands of AI credits on a mid plan and, in its own documentation, call that a one-time grant rather than a monthly allowance. When it runs out, the feature you signed up for stops until you buy more.

Renaming. Plans get renamed more often than they get repriced, and half the comparison articles online still quote the old names. Check the vendor's own page on the day you buy.

I got tired of rebuilding this in a spreadsheet, so it is a free tool now. Give it a monthly price, an annual price and your seat count and it returns the break-even month, with no sign-up.

The rule I settled on: if the break-even month is further out than your confidence in still using the tool, pay monthly and lose the discount. The discount is smaller than the write-off.

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