Insurtech Eye — Insurance Technology News

Thimble and Bold Penguin Launch Agentic AI for Autonomous Small Business Insurance Quoting

By Lauren Towner · 28 September 2026

In brief: Thimble and Bold Penguin have launched an **agentic AI insurance quoting** connection, enabling AI agents to autonomously execute small business insurance tasks for faster broker workflows.

Key facts
PartnerBold Penguin
TechnologyAgentic AI (Agent-to-Agent)
Target MarketSmall Business Insurance
Parent CompanyArch Capital Group
Press Release: Thimble and Bold Penguin Launch Agentic AI for Autonomous Small Business Insurance Quoting | Featured Image by FF News

Thimble, a leading digital small business MGA, announces a new partnership and agentic AI connection with Bold Penguin, the US's largest insurance distribution platform. Thimble and Bold Penguin have co-developed the capability for their systems to discover, communicate, and execute small business quoting tasks autonomously using AI agent-to-agent technologies.

The integration allows Bold Penguin users to leverage natural language supported by AI, to quote and bind coverage faster than ever. Rather than replacing the broker's expertise, the technology is designed to support it, giving producers a quicker and more connected way to serve their clients without stepping outside their existing workflow. This cutting-edge solution opens the door for carriers and brokers to use AI agents to deliver small business insurance policies more efficiently. Working closely with its key distribution partners, Thimble continues to lead how the industry uses new technology to improve the broker and customer experience.

"This is more than an AI technology milestone. It's an early glimpse into how insurance distribution could evolve in the years ahead," said Jay Rajendra, Chief Strategy and Innovation Officer at Arch Capital Group, Thimble’s parent company. "The ability for AI agents from carriers and brokers to communicate and transact business, alongside human decisioning, has the potential to unlock new levels of speed, connectivity, and innovation across our industry. This is not about removing humans from the process, but empowering them in completely new ways. Human expertise, oversight and decision-making remain central to how we develop and deploy these capabilities."

"We are delighted to partner with the Thimble team who share our ambition for intelligent growth,” said Lakshan De Silva, Chief Data & Technology Officer at Bold Penguin. “The work to get it to this stage on data transparency, decision transparency, guardrails, security and compliance was immense, and it is great to see other organizations reciprocate this.”

"Partnering with Bold Penguin allows us to empower brokers with a modern, convenient, and intuitive solution," said Ian Westerman, President of Thimble. "This is about making it effortless for brokers to find the right coverage for their clients in real time, without adding extra steps or complexity. We built Thimble to make small business insurance fast and simple, and this AI-enabled partnership with Bold Penguin extends that promise.”

For more information, visit thimble.com.

Frequently asked questions

How does agentic AI improve small business insurance quoting?

Agentic AI improves quoting by allowing systems to discover, communicate, and execute tasks autonomously. Through the Thimble and Bold Penguin integration, AI agents handle the data exchange in real time, enabling brokers to quote and bind coverage faster using natural language within their existing workflows.

Does the Thimble and Bold Penguin AI replace insurance brokers?

No, the technology is designed to support rather than replace broker expertise. Human decision-making, oversight, and expertise remain central to the process. The AI agents empower producers by providing a quicker, more connected way to serve clients without adding extra steps or complexity.

What is the significance of the Thimble and Bold Penguin partnership?

This partnership represents a major milestone in insurance distribution by enabling AI agent-to-agent communication. It allows Thimble, a leading MGA, and Bold Penguin, the US's largest distribution platform, to unlock new levels of speed and connectivity for small business insurance policies.

About the companies

Bold Penguin

Part of American Family Insurance · Website · 14 stories and 1 video interview on FF News since 2020

Previously on FF News:

Thimble

Part of Arch Insurance Group · Website · 2 stories on FF News since 2026

Previously on FF News:

Companies in this story: Bold Penguin, Thimble

People in this story: Lakshan De Silva, Jay Rajendra, Ian Westerman

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