Category: billing
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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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Operational debt is worse than tech debt
I’ve touched billing systems inside several companies now, and the same pattern shows up every time: the hard part of migrating off seats isn’t the software, it’s the operational debt baked into the business. This is why billing system migrations take at least 8-10 months. You start (well, engineers start) by thinking a pricing change… -
Notes on where seat-based pricing is going
Everyone (mostly me) keeps saying seat pricing is dead, and some people are arguing with me online. I think that’s cool, but it’s because they don’t understand why it’s dying. For twenty years, SaaS revenue scaled with headcount.More humans = more seats.That logic held so long that we stopped questioning it. Then the humans disappeared.… -
The SaaS pricing apocalypse
You know that feeling when you’re looking at your competitor’s pricing page and the math doesn’t add up? $9/month. Unlimited usage. Same features as your $900 enterprise plan. Your first thought: They’re burning VC money. Classic Silicon Valley playbook – grow at all costs, figure out margins later. You’ve seen this movie before. They’ll either…
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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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How we built a mini podcasting studio for under $10,000
The podcast setup at Get Paid was upgraded, focusing on quality and budget-friendly equipment for both remote and in-person interviews. Key choices included the Blackmagic Micro Studio Camera 4K G2 for video, Shure MV7+ microphones for audio, and an organized storage solution. Comfort in the studio environment also significantly enhances interview quality.
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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.…