This is a complete over-simplification, but... I'd start by thinking about how much your product is worth to the company. How much money will it save/make the

This is a complete over-simplification, but... I'd start by thinking about how much your product is worth to the company. How much money will it save/make them? Don't just look at the functionality that you provide, but also at risk reduction. Charging based on value is called value pricing ( https://en.wikipedia.org/wiki/Value-based_pricing https://en.wikipedia.org/wiki/Value-based_pricing ). You'll want to charge less than what your customer has to gain (otherwise they won't buy). This is the number you should be working from (using out-of-pocket costs to determine pricing is called time and materials pricing and is a great way to go broke https://en.wikipedia.org/wiki/Time_and_materials https://en.wikipedia.org/wiki/Time_and_materials). Your original app pricing has little to do with what you can charge enterprise customers, because the product that you're offering is different. Yes, your old pricing will act as a bit of a psychological anchor, but if they've contacted you for a custom plan, they are probably willing to spend quite a bit. Source: I write a blog on the subject of product pricing (and wrote a book specifically about software pricing - http://taprun.com/pricing/ http://taprun.com/pricing/ ).