Tag: billing
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Extend or replace – how to evaluate your billing stack at AI scale
I managed billing for 200+ price points and 14 engineers. Here’s the 6-question framework I wish someone gave me to decide whether to extend or replace a billing stack at scale.
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Building a billing system is still hard, even with AI
8 years building billing systems and I’m still wrong about just how hard it actually is. Not “getting better at it hard”, but like really genuinely discovering new layers of complexity I never saw coming. — Back when we started Paid at the end of 2024, I remember people telling me “billing is not hard,…
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The “stranded asset” in AI pricing
With hybrid “AI pricing”, users face siloed entitlements, creating “stranded assets” where purchased credits remain unused. This misalignment leads to significant churn risks as companies reassess value versus spend amid rising AI costs and limited access to resources.
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🐙 The 14 pains of billing for AI agents
(Basically, why the octopus grew new tentacles for agentic billing) A while ago, I wrote about the 14 pains of building your own billing system – that was back when billing was “just” complicated. It got mentioned quite a bit around the internet, and ended up #2 on the front page of Hacker News which…
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🤔🔍 B2C billing is actually harder than B2B billing
We all love a B2B SaaS ❤️. A few months ago I wrote about 14 reasons why building your own billing system (mostly for B2B SaaS) is hard. Here are 6 more so that we can round it up to a nice 20! While we all really do love a B2B, we often neglect to…
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🦑 The 14 pains of building your own billing system
Trying to cobble together your own billing system is like wrestling an octopus that’s armed with tax codes and invoices instead of tentacles. It’s a beast of complexity that can tangle up everything from customer support to compliance. I have 14 points on why it’s hard.
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You’re pricing your SaaS wrong but that’s probably OK
Previously, I wrote about how important it is to Design your pricing and tools so you can adapt them later – now I want to give a little bit more material on that… I’m going to assume that you’re some sort of SaaS founder, or perhaps even a product manager for pricing, growth, or monetisation.…
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Design your pricing and tools so you can adapt them later
In this blog post I’ll talk about three pricing architecture concepts that I think are really important in modern billing – designing pricing and packaging to be adaptable. I’ll build upon the experience our billing infrastructure team had at Pleo, which has allowed us to expand to new geographies, currencies, and adapt pricing very rapidly.…
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How we built a Cashback system with Stripe
Recently, at Pleo, we built a cashback system that uses our internal payments infrastructure, as well as Stripe. So while there are other components at play to actually move the money around, Stripe is what drives the cashback events for the most part. Yeah, it’s a bit of a stretch, but it is doable! I’m…
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You should separate your billing from entitlements
Building your own entitlement service is key for supporting a modern, flexible SaaS product. Whenever I read about billing systems, there’s a lot of talk about the billing aspects but not so much around entitlements. In the spirit of sharing, and since I haven’t found any good articles about it, I decided to tell you…