For GTM, marketing, and distribution leaders navigating the shift from traditional to AI-native channels across financial services.
There is a particular kind of marketing that insurance companies excel at more than almost any other industry. Not the dry, compliance-heavy, small-print-at-the-bottom kind one would think. But another kind — the kind that often becomes genuinely cultural.
Think about what Comparethemarket did with Aleksandr Orlov. A CGI meerkat with a Russian accent became one of the most recognised brand assets in British advertising history, not because it explained insurance particularly well, but rather because it understood something deeper about how people relate to financial products they don't really want to think about. They made it memorable, slightly absurd, impossible to ignore, and easy to talk about.
Direct Line brought in Harvey Keitel as Winston Wolfe, a fixer from Pulp Fiction, to tell customers they didn't need a comparison site because Direct Line would come to them. Genius. The implicit message conveyed confidence bordering on arrogance, and it worked, really well!
Admiral built an entire brand around being slightly cheeky in a sector that had forgotten how to have a personality. AXA's "Know You Can" campaign ran across outdoor, digital, and sponsorship for years, weaving the emotional case for insurance by evoking feelings of protection, certainty, and peace of mind through some of the most creatively ambitious work the category had seen.
The challenger brands have pushed this instinct furthest. Naked Insurance, a South African InsurTech founded by three actuaries, built one of the most talked-about OOH campaigns in recent memory — over 150 unique billboards across South Africa, each showing a real time and place where a customer had bought insurance from their smartphone. Padel courts, dentist waiting rooms, rugby stadiums.
The campaign generated nearly 20 million organic TikTok views without a single paid celebrity or scripted testimonial. The creative insight was also the truth behind the product: insurance so simple you can get it anywhere.
These campaigns were successful because the CMOs behind some of the largest insurance companies understood something fundamental: insurance is often not a product people specifically seek out. It's a product people are reminded of, often in times of uncertainty, during other large purchase decisions (like buying a house), or during times of change (moving countries, going on holiday, adopting a pet dog), which means distribution and marketing are embedded and should always be planned and executed in parallel.
The channel through which a consumer encounters your brand for the first time is inseparable from how they feel about buying from you. That insight has never been more important than it is right now, because, as we're all painfully aware, the channel has just changed again.
The Aviva moment
In March 2026, Aviva announced it was launching the first UK insurer app on ChatGPT, as covered by Insurance Post. Some industry observers have debated whether this was premature, and one former price comparison executive questioned whether ChatGPT could really become a dominant distribution force.
These are reasonable questions, but they miss the point of what Aviva actually did. Aviva did not launch a ChatGPT app because they had certainty it would generate meaningful premium volume in year one.
They launched it because they understood that the CMOs who wait for certainty before entering a new distribution channel are the same CMOs who spent 2004 debating whether people would really use the internet to buy insurance.
The pattern in this industry is consistent. Every major distribution innovation, whether that's the aggregator, the direct channel, the price comparison website, or embedded insurance, was dismissed as marginal by incumbents until it wasn't. The window between early mover and laggard closes faster than anyone predicts. Aviva has a long history of moving before the window closes, so it's no coincidence that they're one of the most recognised insurance brands in the UK.
Where consumer attention actually is
ChatGPT handles over a billion queries per week. Think about that for a second. Over a billion. A growing and measurable proportion of those queries are purchase-adjacent, for queries like "What life insurance do I need?", "Is my home underinsured?", "What's the best income protection for a freelancer?"
These are the opening moments of a buying journey, and they're happening inside AI assistants. Increasingly so, these queries are not taking place inside Google, comparison sites, or inside a broker's office; they're happening inside ChatGPT, Claude, and Perplexity.
As Malcolm's Founder, Tim Graham, mentioned last week, and according to Insurify, 42% of drivers have already used an AI assistant to help shop for car insurance. In younger demographics, that figure rises to 60%. That represents a seismic, structural shift in where insurance intent is forming and where insurance marketing (and quoting, binding, and purchasing) needs to be present.
The CMOs who built careers on SEO, aggregator relationships, and above-the-line brand spend aren't wrong about what worked. However, they may well be wrong if they assume it'll keep working at the same rate. Google's share of purchase journeys in financial services is declining as the queries that used to start with a search engine are increasingly starting with a conversation.
Soon, we're going to share some insights on which insurers are appearing in AI most — in which lines. But visibility without transactability is a half-built distribution channel. Consumers are already asking ChatGPT and Claude for insurance quotes. The ones who appear in the answer but can't complete a transaction in that same conversation are losing the sale at the final step.
Anthropic and OpenAI have both now opened their platforms to insurance providers, meaning compliant, real-time quoting and purchasing directly inside Claude and ChatGPT is no longer theoretical.
The CMO question has shifted. It's not whether to be visible in AI. It's whether being visible actually converts.
The great campaigns still matter, but the channel has changed
None of this means that creative excellence is dead. In fact, in a world of AI-generated content and creativity, it's quite the opposite. Creative excellence and human-centric campaigns have never been more important. The brands that will win AI distribution are the ones that have already done the work of being memorable, trusted, and well-defined in the consumer's mind. Aleksandr Orlov exists in ChatGPT's training data.
The emotional associations built by two decades of brilliant insurance advertising are part of the context an AI like ChatGPT or Claude draws on when it makes a recommendation, and that'll continue to be the case.
But this emotional resonance alone is no longer enough. For a brand to be recommended, quoted, and transacted inside an AI environment, the underlying infrastructure has to exist. The pricing engine has to be accessible, the underwriting logic has to be queryable, and the compliance layer has to be in place so that a hallucinated coverage limit doesn't become an FCA breach.
What does the next great insurance campaign look like?
The best insurance campaigns of the last thirty years shared a common characteristic: they met consumers where the consumers actually were. Comparethemarket understood that people wanted to compare, so they made comparison feel less painful. Direct Line understood that people resented the middleman, so they cut him out. GoCompare understood that people found insurance boring, so they made it annoying enough to be memorable.
The consumer is now inside an AI assistant.
The question for every insurance CMO is the same question that the best ones have always asked: how do we show up, meaningfully and safely, in the place where our customers are making decisions?
The insurers building the answer to that question right now are the ones who will look back in ten years the way the early aggregator adopters look back today. The insurers who layer consumer-facing distribution from a marketing standpoint with the ability to quote, price, bind and purchase quickly and compliantly within chat-based platforms are, put simply, going to win.
The infrastructure to make it happen compliantly by connecting pricing engines to AI channels without hallucination risk, without FCA exposure, and without rebuilding core systems, is being rolled out now.
The takeaway: The CMO conversation and the CTO conversation are, for the first time, the same conversation.
Malcolm is building the compliant infrastructure layer that connects insurance products to AI distribution channels. If you're thinking about what AI-native distribution looks like for your organisation, we'd be glad to show you how it works.