Hey Alex, this is a really important question and one that most companies answer with homegrown systems. This often leads to reinventing the wheel, driving up engineering costs, and constraining business agility. We've written in depth about how to implement & operate pricing from a systems & architecture perspective. https://schematichq.com/blog/how-to-operate-pricing-and-packaging I've also curated 10 of the best articles I've come across related to the question you're asking here: https://www.linkedin.com/posts/fynn-glover-b0410015_10-useful-actionable-reads-for-product-activity-7260732669955555328-20Ac?utm_source=share&utm_medium=member_desktop What's key is that you decouple pricing & billing from application code, so you can remove engineering from having to support future changes, and empower the business to iterate as your product & market evolve. To do this, would encourage you to make entitlement management a first-class citizen in whatever path you go down. You could build or outsource an entitlements system. If you outsource, here are a few vendors to evaluate: - if your company is quite large (e.g. $100M ARR+), you might look at license management providers like Thales, Revenara, Nalpeiron, Stigg, etc. - if your company is a startup, you might look at my company Schematic (https://schematichq.com/) - some companies try to solve this through their billing provider (e.g. chargebee, stripe, etc), but they still have to build logic between their application and the downstream billing tools, which usually means engineering is always critical path in pricing changes/initiatives. Hope this is helpful, and happy to connect on this anytime, as it's an important question.