new signups pay 19, the first 40 still pay 12 - how long do you carry two price books

Grandfathered my first cohort permanently and I would do it again, but go in with eyes open about what it costs. Mine is around 210 a month in revenue I am not collecting, and it has bought me a group of people who answer surveys, send bug reports with steps, and have referred more customers than any channel I have paid for.

The operational fix is naming. Stop calling them tiers and start naming prices by date - standard-2025, standard-2026. When someone emails, the answer to which price am I on is in the price name rather than in your memory, and it makes the next increase a new name rather than an edit.

Thirty accounts times seven is 210 a month, about 2,500 a year. Model the migration before you do it: assume you lose 10 to 15% of the migrated cohort, so call it four accounts, and you keep roughly 26 x 19 = 494 instead of 30 x 12 = 360. That is a gain of about 134 a month, and you have spent goodwill you cannot re-earn.

The version that has worked for me is a middle path: sixty days notice, and the offer to lock the old price for one more year by moving to annual. Most of the cohort took the annual lock, which gave me the cash up front and moved the awkward conversation twelve months out.

Forever is a promise you cannot keep and should stop making. Costs move, and in five years the honest position will be that 12 does not cover what serving that account costs.

What I do now is one sentence in the terms from day one: your price is held for twelve months from signup, changes are announced at least sixty days ahead. That converts every future increase from a betrayal into an operation.

Carry it until the accounting annoys you more than the churn risk scares you. For thirty accounts that is probably another year.

Did this migration two months ago with 33 people on the old price. Sixty days notice, two emails, and two people cancelled.

The email that worked was short and had no apology in it. First line said what is changing and when, in numbers - your plan goes from 12 to 19 on 1 March. Second paragraph, one sentence on why, which for me was honest: support and hosting per account roughly doubled since I set that price. Third, the options - stay monthly at the new price, lock twelve months at the old price by switching to annual before the date, or export everything and leave with no hard feelings, here is the link. Fourth, a direct reply-to-me line.

Most of the replies I got were people asking to be moved to annual immediately.

On the mechanics, set the proration behaviour explicitly rather than taking the default, and schedule the change to take effect at the end of the period. Silent mid-cycle price changes generate exactly the kind of surprised charge that turns into a dispute rather than an email. Also click through your own billing portal afterwards and check that the amount shown there matches what you announced.