We just felt it was fair, clear, and simple. One price. Do you want to buy Basecamp? If so, here’s the price. Simple. One decision to make - yes or no - rather than deciding on different tiers, different feature sets, doing the math to figure out how much it might cost if you have 17 employees vs 32 vs 587. Basecamp is $99/month flat no matter how many people you have. That’s how I’d want to buy Basecamp, so that’s how we sell Basecamp. We also just released a Personal version that’s totally free, but there’s only one price for the paid version (although we do offer two months free if you pay annually for $999).
Certainly we’re leaving money on the table - plenty of large companies spend thousands of dollars a month on our competitors - but that’s fine. We’re not interested in making every last dollar, or squeezing every last penny out of a transaction. We feel that overall, a single price is the clearest and fairest.
We also think a single price insulates you significant losses if a big customer was to leave. The worst customer to have is one you can’t afford to lose. We don’t want to lose customers, of course, but we can afford to lose anyone at any time since the most anyone pays us is $99/month. I wrote about in detail here: https://m.signalvnoise.com/a-static-business-is-a-healthy-business/