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I can't help but wonder whether leaving money on the table and leaving complexity on the table are correlated to such a severe degree at every price higher than $150.

Big customers are dangerous, and I've seen businesses where I have worked (ad agencies) operate completely out of fear of losing the big accounts.

But is there no middle ground between $150/mo and thousands/mo? What about $250/mo or $500/mo? Would tiers like these necessarily add complexity?

Obviously, it depends on the data. Speculation: a handful of customers paying $250/mo might not justify the dev time needed to implement the new plan or the risk introduced by pricing changes.



This is a good question, and the truth is there actually isn't much of a middle ground between a few hundred dollars/month and thousands or tens of thousands.

The reason is purchase process. Any purchase above a certain about usually has to go through the procurement department at a large company, which means that any sales above that amount become very expensive. That's why there's such a big gap in software prices.




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