The move marks Pie’s entry into its 39th state, plus Washington, D.C., and extends its nationwide customer base beyond 50,000 policyholders. The company continues to grow through embedded partnerships, independent agencies, and direct-to-consumer online channels.
Pie leverages proprietary AI and machine learning technology to deliver instant pricing decisions for 73% of class codes, enabling faster quotes, more accurate risk assessment, and streamlined binding for agents. This approach aims to address long-standing challenges for Connecticut’s small businesses, which often face limited insurance options and higher premiums from traditional carriers.
“Connecticut’s economy depends on small businesses, which make up more than 99% of all businesses in the state,” said John Swigart, co-founder and CEO of Pie Insurance. “Whether you’re running a family restaurant in New Haven or a construction company in Hartford, you deserve coverage that understands your business and prices risk fairly.”
The company also emphasizes workplace safety, citing its 2025 Workplace Safety Survey, which found that 50% of small business injuries are preventable, with average costs exceeding $10,000 per incident. “We go beyond paying claims,” added Carla Woodard, Senior Vice President of Claims at Pie. “We’re providing practical insights to help employers maintain safer work environments.”
Pie’s Connecticut launch is supported by its network of more than 5,000 appointed agencies, now able to offer local businesses access to its data-driven workers’ compensation solutions.
