The $500 Cliff: Why Good Buyers Disappear Between Your Cheap Plan and “Contact Sales”
Picture a buyer who has already said yes twice. They tried your product, liked it, paid for the entry tier, then upgraded to the next one without blinking. Then they ask for one more seat, one more workspace, one more integration — and the price jumps from $29 a month to $500 a month, prepaid, no negotiation. They don’t complain. They don’t ask for a discount. They just quietly close the tab. Most founders will never know that customer existed, let alone that they almost bought.