WASHINGTON, DC – January 13, 2026 – Pie Insurance, an insurtech specializing in commercial insurance for small businesses, today announced significant milestones achieved in 2025, including expanding its workers’ comp offering to Connecticut, surpassing 55,000 policies in-force, and growing its partner agent network to more than 5,000.
"Reaching 55,000 policies represents 55,000 small businesses that can focus on growing instead of wrestling with complicated, overpriced workers' comp insurance," said John Swigart, CEO of Pie." We're building the scale and reach to fundamentally change how America's small businesses access coverage and stay protected. We’re on a path to see meaningful market impact and disciplined growth in 2026."
Key 2025 Milestones
Pie achieved several noteworthy business milestones in 2025:
Industry Recognition and Workplace Excellence
Pie received multiple honors recognizing both its business performance and commitment to workplace excellence as a remote-first organization:
Filling the Small Business Workplace Safety Gap
Pie strengthened its position in 2025 as a workplace safety authority with two major research initiatives. The first one, Pie’s State of Workplace Safety Report revealed that 75% of small businesses reported workplace injuries, with half being preventable. Also, Pie’s Employee Voice on Workplace Safety Report uncovered "The Great Safety Divide," highlighting a significant gap between employer perceptions and employee experiences, including that 28% of workers never received formal safety training despite 63% of employers believing they provide it.
“There’s a massive gap in actionable safety resources for small businesses,” said Carla Woodard, SVP of Claims at Pie. “They need more than just coverage. They need support in understanding ways to prevent injuries before they happen. From the growing mental health crisis in workers to fundamental gaps in training, our safety research program helps us understand the real challenges small business owners and their workers face. We’re excited to dive even deeper into the data next year as we continue to help small businesses create safer, healthier workplaces.”
Looking Ahead With AI-Driven Efficiency and Industry Evolution
For 2026, the company expects continued pressure across the small commercial insurance industry to deliver faster pricing, improved accuracy, and lower operating costs.
Throughout 2025, Pie made significant investments in AI and advanced analytics to improve underwriting speed, pricing precision, and operational efficiency. These investments enable the company to pass savings directly to policyholders and partners through competitive pricing and faster, more self-service products.
"The small business insurance market is at an inflection point," said Swigart. "We're seeing hardening rates in some segments while competition intensifies in others. The insurers who win will be those who can leverage AI and advanced analytics to price risk more precisely, process submissions faster, and deliver genuine value to both policyholders and agents. Our focus in 2026 will be on responsible growth, continued strategic geographic expansion, providing unique safety resources to small businesses, and deepening our partnerships with the agent community. We believe the combination of sophisticated technology, granular pricing, and strong agent relationships positions us uniquely as small businesses continue to navigate an uncertain economic environment."
Learn more about Pie at www.pieinsurance.com.
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.
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