If pricing is adjusted on a regular basis, it trains your customers to understand that the value is going to be changing as the product is improving. The worst thing you can do is add so much value over the course of three to five years — even 12 months — and then all of a sudden want a big bump from your customers who have gotten used to paying a specific amount. That shock is what leads to pissed off customers and churn, not necessarily the higher prices. […] So what should you do? Every three to six months there should be changes, but you shouldn’t be effectively raising the price every three to six months on someone. Don’t make people pay more for what they have, essentially lowering their value metric. Add in a feature to the enterprise tier and get people to upgrade. Or introduce a related plan with a slightly higher value metric and price. Those are ways that you can effectively make sure you’re constantly evolving and optimizing your pricing.
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