a third of signups are from places where $29 is a lot — is regional pricing worth the leakage

Ran a two band country list for about a year, roughly forty five percent off in the lower band.

Leakage was not the problem. Maybe three accounts I could not explain out of a few hundred. The actual cost was support and awkwardness: people who moved countries, people whose company card was issued somewhere else than they live, and the one customer who found the list and asked why their country was not on it in a tone I remember to this day.

Revenue effect was positive but modest. Conversion in the lower band roughly doubled off a low base. If you do it, publish the list openly rather than hiding it behind a code. Hiding it is what generates the resentment.

Size the prize before you build anything, because for most people at this stage it is smaller than it feels.

Work out what share of your revenue those regions represent today, and then what they would represent at the discounted price with a generous conversion assumption. If the honest answer is that a successful programme adds a couple of hundred a month, ask whether that beats the same hours spent on the segment already converting at four times the rate.

On the mechanism: gate on the card country at checkout, not on IP. IP is one browser extension away from being whatever someone wants. The country the card was issued in is a much harder thing to fake, and your payment provider exposes it on the payment method. You can also let anyone claim the discount and check the card country afterwards, then email the handful that mismatch. Blocking costs you real customers, checking afterwards costs you an email.

Politely, no. Not at your size.

Regional pricing is an optimisation for a company with a pricing person and a billing team. What it costs a solo maker is a permanent second price list to reason about every time you change anything, plus a support surface, plus the risk of the awkward public conversation about which countries you decided are poor.

The same problem has a simpler answer: ship a genuinely cheaper plan with less in it, available to everybody, and let annual billing carry the rest of the discount. Nobody feels judged by a smaller plan.

Whatever you pick, do not run it as a coupon code that spreads. Attach it to the account at checkout based on the card, or it will end up on a deals site within a month.

Small thing that helped me before I did anything structural: I added a line under the price saying if this is out of reach where you are, reply and tell me what works. Six people replied in two months. Four of them are paying something. It is not a system and it does not scale, but at forty customers you do not need a system, you need four conversations.