South African insurtech Naked Insurance just did something that sounds small, but might actually be one of the more significant tech moves to come out of this country in a while.
They’ve built what they’re calling the world’s first ChatGPT-native insurance app that spits out a real, binding car insurance quote — inside ChatGPT itself. This is not a “leave your number and we’ll call you.” It’s sn actual quote, hooked up to a live underwriting engine.
That difference matters more than it sounds.
For years, “AI in insurance” was basically fancy autocomplete on a call centre script, or a website chatbot that made you feel productive before eventually dumping you into a queue. This is very different. Naked’s integration talks directly to the same backend that powers their website and app. The quote you get in ChatGPT is the same one you’d get going through their normal process.
Remember When Getting a Quote Took Three Hours?
If you’ve ever tried to get car insurance in South Africa, you know the drill. Google around or fill in your details on hippo.co.za, then spend the next two weeks dodging calls from a consultant named Charl.
Naked built their whole brand around killing that experience. When they launched in 2018, they were already the weird kid — fully digital, no call centres, AI-driven from the start.
This is just them leaning further into that same bet.
Now instead of going to any website, you could theoretically just type: “I want to insure my 2021 Polo Vivo” into ChatGPT, answer a few follow-up questions, and walk away with an actual quote in the same conversation. Most importantly, there’s no Charl.
But Here’s the Part That Should Actually Make You Think
The real story is what happens when AI assistants become the main gateway between South Africans and financial products. Naked’s co-founder Alex Thomson has already been floating the idea that AI agents could eventually compare policies across insurers, track your renewals, explain cover in plain language, and potentially even switch providers for you automatically.
If that future arrives, comparison websites start looking like Nokia phones. Your insurer’s app matters less and SEO budgets become a lot less useful. Even brand loyalty gets complicated when an AI is making the choice on your behalf.
Insurance companies won’t be competing for clicks anymore. They’ll be competing to be the one an AI recommends.
That’s a very different game.
SA Isn’t the Only One Playing, But Naked Is Early
Spanish digital insurer Tuio had a go at something similar with ChatGPT quoting. But Naked appears to be among the first globally and almost certainly the first in South Africa to deliver a fully binding vehicle insurance quote natively inside ChatGPT.
Timing counts. OpenAI only opened its apps SDK to outside developers in late 2025, which means this whole category is still brand new territory. Early movers don’t just get the tech advantage — they get to be the brand people associate with the shift.
The Catch Nobody Has Figured Out Yet
Insurance is one of the most regulated industries in South Africa. And regulators haven’t exactly caught up to this yet.
Once an AI starts facilitating or recommending a financial product, things get complicated fast. Who’s liable if the AI misunderstands your situation? What counts as financial advice under FAIS? How transparent does an AI-generated recommendation need to be when it’s embedded inside a ChatGPT plugin?
The FSCA is going to have opinions about this eventually. And those opinions might take a while to arrive.
There’s also the hallucination problem. Naked themselves have acknowledged it — which is why their integration includes confirmation steps. Language models still occasionally make things up with complete confidence. That’s fine when someone asks ChatGPT to write a birthday card. It’s less fine when it’s generating the price of your car insurance.
The technology feels advanced enough to trust emotionally, but the legal infrastructure to actually trust it hasn’t arrived yet.
The Bigger Shift
What Naked launched is technically a ChatGPT insurance plugin.
But what it actually represents is the beginning of a new layer of the internet — one where you don’t go to apps and websites anymore. You just talk to an AI, and the AI goes to the apps and websites on your behalf.
Shopping. Banking. Insurance. Healthcare. Travel bookings.
The question used to be: “Do you have an app?”
The new question is: “Can I use AI to do business with you?”
Most South African companies don’t have an answer to that yet. Naked at least has a head start.
