As small businesses seek faster and simpler insurance solutions, traditional quoting processes continue to create friction through lengthy applications, manual data entry, and complex workflows. Thimble and Bold Penguin are addressing these challenges through an AI-powered quoting integration that combines natural-language processing with agent-to-agent (A2A) technology and the Model Context Protocol (MCP). The integration enables producers to describe client needs in everyday language within the Bold Penguin platform, assess eligibility, and obtain bindable quotes for qualifying policies while retaining human review and oversight. In an exclusive conversation with AI Reporter America, Ian Westerman, President of Thimble, discussed how the integration is streamlining small-business insurance quoting, reducing manual effort, and creating a more scalable approach to connecting producers with coverage options.

1. What drove Thimble and Bold Penguin to build an AI-powered quoting integration?

Thimble has been focused on making small business insurance simple and fast. Extending its intuitive quoting experience into an AI enabled platform using agent to agent AI and MCP technology was an obvious next step. Bold Penguin’s broad distribution network and advanced technology made it an ideal partner to bring this capability forward together for small business quoting.

2. How does the integration simplify and accelerate insurance quoting?

By leveraging the way that LLMs ingest prompts in the form of natural human language, users can build a custom quote inside the Bold Penguin interface where they already are, and enjoy a near-instant throughput bind (for qualifying policies) without the traditional method of filling out a digital (or worse, paper) application. This speeds up the portion of the process that precedes the human review.

3. What makes this approach different from traditional insurance quoting workflows?

The integration between the two systems enables producers to use natural language to create quotes, which greatly improves speed to market, and is a major improvement for how producers traditionally build quotes. The scalability of this technology will continue to improve that speed without complex integrations.

4. How does AI reduce manual work for agents and brokers?

Instead of manually entering data into appetite and quoting tools, agents and brokers can describe the client and coverage needs in natural language. The AI then assesses eligibility and appetite fit and, when sufficient information is available, can return a bindable quote. It also provides a link for client approval (i.e. human review), further streamlining the process and reducing the risk of human error.

5. How does the integration improve quote accuracy and carrier matching?

The accuracy of the returned quote is the same as filling out an application because the same eligibility criteria must be answered in both experiences.

As more carriers and MGAs develop A2A capabilities to partner with comparative raters like Bold Penguin, producers will be able to reach multiple options for coverage with the same natural language queries.

6. How are Thimble and Bold Penguin addressing security, transparency, and data accuracy?

This topic is of utmost importance to Thimble and Bold Penguin, and as such it is imperative for our brands to engage in only trusted partnerships. As part of these trusted partnerships, strict, agreed-upon security measures and guardrails have been implemented, such as tracing for all agent interactions. Finally, inputs and outputs for the quote are fully reviewable and revisable by the producer/broker to help ensure quote accuracy. As technology evolves, so must our approach to security, transparency, and data accuracy./

7. How could AI-powered quoting reshape the future of small-business insurance?*

AI-powered quoting will ultimately provide agents and customers more choices when selecting coverage and will help them identify the best coverage for their business. Thimble’s goal has always been to create an experience that matches the speed at which our customers operate, and this integration is another step in achieving that vision for customers.

This technology also enables agents to quote faster and more simply, streamlining their workflows so scaling becomes easier.

Finally, for comparative raters or other agency groups, this technology may eliminate or reduce typical downtime historically coupled with API maintenance and releases.