Washington, DC —August 12, 2025 — Pie Insurance, a leading insurtech specializing in commercial insurance for small businesses, announced the launch of its workers’ compensation insurance in Connecticut, making affordable and tailored coverage available to more than 365,000 small businesses across the state.
With this latest expansion, Pie now offers workers’ comp in 39 states and Washington, D.C., serving more than 50,000 policyholders nationwide. Connecticut becomes the latest addition to Pie’s growing national footprint, as the company continues to scale its presence through a diverse mix of embedded partnerships, independent agencies, and direct online services.
Data-Driven Insurance Built for Small Businesses in Connecticut
Connecticut small business owners and licensed insurance agents now have access to Pie’s data-driven workers’ compensation insurance. The company’s proprietary AI and machine learning pricing technology delivers instant decisions on 73% of class codes, enabling faster quotes and more accurate pricing for businesses historically underserved by traditional insurers. Pie streamlines the quoting and binding process for agents, enabling them to serve their small business clients more efficiently than ever before.
Pie’s technology-driven approach addresses longstanding challenges in Connecticut’s workers' compensation market, where small businesses often face limited options and higher premiums due to traditional insurers' inability to granularly assess risk for diverse business types.
"Connecticut's economy depends on small businesses, which represent more than 99% of all businesses in the state," said John Swigart, co-founder and CEO of Pie Insurance. "At Pie, we believe every business warrants coverage that fits their reality. Whether you're operating a family restaurant in New Haven or a construction company in Hartford, you deserve insurance that understands your business and prices risk fairly."
Supporting Safety Where It Matters Most
Connecticut's diverse economy spans healthcare, construction, retail, professional services, manufacturing, and food service—industries with varying safety requirements and risk profiles that demand specialized understanding.
The Pie Insurance 2025 Workplace Safety Survey found that 50% of small business injuries are preventable, with average out-of-pocket costs exceeding $10,000 per incident. For Connecticut’s small businesses, this represents significant potential savings through proper coverage and proactive safety measures.
“Small businesses often operate without HR teams or safety departments,” said Carla Woodard, Senior Vice President of Claims at Pie. “We go beyond servicing policies and paying claims. We’re providing practical insights that help employers to create and maintain safer work environments.”
Pie continues to grow its national network of over 5,000 appointed agencies, enabling licensed insurance professionals in Connecticut to offer clients access to tailored workers’ compensation solutions. Agents interested in partnering with Pie for workers’ compensation insurance in Connecticut can learn more and get appointed at pieinsurance.com/agents.
About Pie Insurance
Pie Insurance is leveraging technology to transform how small businesses buy and experience commercial insurance, with the goal of making it affordable and as easy as pie. Pie's intense focus on granular, sophisticated pricing, and data-driven customer segmentation enables Pie to match price with risk accurately across a broad spectrum of small business types, which allows Pie to offer more affordable insurance to small business owners. Since 2017, Pie has received more than $615 million in funding and partnered with more than 5,000 agencies nationwide.
Allie Pergram
Email: media@pieinsurance.com
