Naked Insurance has made a bold move into the next phase of AI-powered finance, launching a native app in ChatGPT that can generate a final, binding car insurance quote. For the Johannesburg-based insurtech, this is not just another tech experiment — it is, according to the company, a world first on OpenAI’s apps platform and a sign of where insurance shopping may be heading in South Africa and beyond.
The new app is available through ChatGPT’s app directory and connects directly to the same underwriting and rating engine that drives Naked’s website and mobile app. In practical terms, that means users are not merely getting a rough estimate or a sales lead. They are getting a real quote, with the premium shown inside ChatGPT matching the price they would actually pay.
That distinction matters. A lot of the AI tools that have emerged in insurance so far have focused on conversational lead generation: asking a few questions, collecting contact details, and handing the user off to a human consultant or a separate quote flow. Naked says its approach goes further by allowing a customer to complete the quoting process within the chatbot environment itself.
Users can answer questions in plain language, rather than filling in a traditional online form. They can also adjust variables such as the excess and immediately see how that changes the premium. That kind of interactive pricing experience is exactly the sort of thing AI assistants are being marketed to do, but in insurance, the stakes are much higher because the output can affect a binding financial decision.
The timing is also notable. OpenAI opened its apps software development kit in October 2025, which means the field is still very small and largely experimental. Naked has moved early, positioning itself among the first developers to test how a consumer-facing financial service behaves inside a mainstream AI assistant.
For a South African insurtech that has spent years building its brand around digital-first convenience, the launch fits neatly into its wider strategy. Naked was founded in 2018 by actuaries Alex Thomson, Sumarie Greybe and Ernest North, and its car insurance products are underwritten by Hollard. The company has always leaned heavily on automation and technology, but this new step takes that promise into a much more conversational, AI-native environment.
Thomson was clear that the company is not abandoning its own platforms anytime soon. “Our app and website are still the best way to use Naked today,” he said. “But we believe AI assistants will, in time, become one of the primary ways people interact with financial products and we want to be ready for that next industry shift.”
That comment reflects a broader trend in global finance. Banks, insurers and investment platforms are all wrestling with the same question: if people increasingly ask an AI assistant to compare, explain and even purchase financial products, who controls the customer relationship? The interface may be chat-based, but the underlying product still needs to be accurate, compliant and fully auditable.
Naked Insurance ChatGPT app could reshape how South Africans buy cover
For South African consumers, the launch of the Naked Insurance ChatGPT app raises both opportunity and caution. On the one hand, the idea of getting a proper car insurance quote through natural conversation could make the process faster, simpler and less intimidating. On the other, insurance is a tightly regulated financial product, and shifting part of the journey into a third-party AI layer introduces important questions around disclosure, advice and accountability.
That is where the Financial Sector Conduct Authority may eventually come into the picture. South Africa’s advice and intermediation rules are designed to protect consumers when financial products are sold or explained. If an AI assistant delivers a quote that becomes binding, regulators may need to determine how those rules apply when the interaction happens inside a platform controlled by another company.
There is also the issue of consumer expectations. Many people still use ChatGPT as a general-purpose assistant, not as a financial service portal. If a user asks for a quote in a casual way, the system still needs to ensure the process is clear, precise and transparent about what the customer is agreeing to. That is especially important in insurance, where wording, exclusions and excess choices can materially affect cover.
Naked’s launch is likely to attract attention not only because it is first-of-its-kind, but because it sits at the intersection of three fast-moving sectors: insurtech, generative AI and financial regulation. The company is effectively testing whether a chatbot can become a legitimate sales channel for a regulated product, not just a support tool or marketing layer.
For investors and competitors, that will be worth watching closely. South Africa’s insurance market is already crowded and highly price-sensitive, with digital convenience increasingly shaping consumer choice. If Naked can prove that a quote generated inside ChatGPT is both seamless and trusted, it may open the door for other insurers to follow.
At the same time, early adoption does not guarantee mass take-up. Consumers will still need reasons to move beyond the familiar website and app experience. Trust, speed, pricing and ease of use will all matter. So too will the ability of AI platforms to handle sensitive data responsibly and consistently.
As we reported earlier, Naked has been one of the more aggressive local players in funding and product innovation. The company recently raised R700-million in its biggest funding round to date, giving it the firepower to keep pushing into new digital territory. This ChatGPT launch looks like another signal that the business wants to stay ahead of the curve rather than wait for the market to catch up.
Still, the bigger question remains unresolved: will AI assistants genuinely become a main way people buy insurance, or will they remain a clever novelty for early adopters? Naked clearly believes the answer is the former, and this launch is its bet on that future. For now, the Naked Insurance ChatGPT app is more than a marketing stunt — it is a live experiment in how far conversational AI can go in one of the most regulated corners of consumer finance.