Insurance Quoting Enters the AI Conversation Layer

Getting a price on small business insurance has always meant answering a long list of questions across multiple touchpoints before reaching anyone who could give a number. On Thursday (April 23), Simply Business compressed that process into three data points inside a ChatGPT conversation.

Simply Business, a digital insurance marketplace for small businesses and a subsidiary of The Travelers Companies, launched a business insurance app inside ChatGPT in the U.S., connecting the platform’s conversational interface to its pricing engine. Small business owners can receive an indicative price by entering their business type, estimated annual revenue and ZIP code, then are directed to the Simply Business website to complete the full quote and purchase a policy. No personally identifiable information is collected inside the ChatGPT interface.

The launch marks a specific shift in where artificial intelligence (AI) intersects with insurance revenue. Prior deployments in the sector have focused on claims processing, underwriting models and customer support. This launch puts AI at the quoting stage, directly in the path of a sale.

Quoting as the New Distribution Front Door

Insurance distribution has historically run through agents, brokers and direct channels. A business owner researching coverage would find an insurer’s website, fill out a form, wait for a callback or speak to a broker. The intent formed somewhere. The transaction happened somewhere else.

The Simply Business app sits in ChatGPT’s App Directory and can appear as a recommendation when users ask questions related to business risk and insurance, the company said. That placement captures intent at the moment it forms, inside the interface a small business owner is already using to research, plan and make decisions. The quote doesn’t require navigating to a separate platform first.

“Small business owners are already using platforms like ChatGPT to research, plan and make decisions. By safely bringing insurance pricing into that environment, we’re removing one more barrier between them and the coverage they need,” Dana Edwards, Group CTO at Simply Business, said in the company’s announcement.

The model keeps ChatGPT firmly at the top of the funnel. Pricing is indicative, not binding. The full quote and purchase happen on the Simply Business platform. The insurer retains control over pricing and policy issuance, while the AI interface handles discovery and first-touch engagement.

Compressing the Workflow

The launch builds on Simply Business’ October rollout of a hyper-personalized AI-powered advisor in the U.S., designed to make the insurance buying process faster and more intuitive by tailoring recommendations to a small firm’s profile and risk characteristics, the company said. The ChatGPT integration extends that strategy into a third-party platform, where potential customers are already active.

This compression matters for revenue. A quoting process that begins and ends inside a single conversation reduces the friction between intent and commitment. The small business owner who asks ChatGPT about liability coverage and receives an indicative price in the same exchange is further along the purchase funnel than one who gets a link to a website.

Simply Business serves more than one million customers across the U.S. and U.K. and offers general liability, professional liability, business owner’s policy, workers’ compensation and cyber insurance through a digital marketplace that matches small businesses with coverage from multiple carriers, the company said.

The broader context for this launch is an industry that has spent decades trying to modernize without fundamentally changing how customers enter the purchase process.

Insurance has been trying to go digital for more than 20 years, but the average underwriter still only gets to about 40% of the submissions that land on their desk, with the rest expiring or getting declined by default, according to PYMNTS. Moving price quoting into a conversational AI interface puts that digitization front and center.

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