Pie Insurance vs Progressive
Side-by-side comparison of AI visibility scores, market position, and capabilities
Data-driven workers' comp for small businesses; raised $300M+; ML underwriting enables fast quotes through digital brokers; one of the largest insurtech workers' comp carriers in the US.
About
Pie Insurance is a Washington, D.C.-based insurtech company that provides workers' compensation insurance to small and medium-sized businesses through a technology-enabled platform. Pie uses alternative data sources and machine learning to underwrite workers' comp policies more accurately than traditional actuarial models, enabling it to offer competitive pricing to businesses in industries like construction, restaurants, and healthcare services. The platform delivers quotes in minutes through a digital flow that connects directly with insurance brokers and agents, who remain central to Pie's distribution strategy. Founded in 2017, Pie has raised over $300M from investors including Accel, Greycroft, and Moxley Holdings and has grown to become one of the largest insurtech workers' comp carriers in the United States. Pie's model captures the small business segment that is often underserved or overpriced by traditional carriers who rely on limited data for these accounts.
Mayfield Village OH #2 US auto insurer (NYSE: PGR) at $75.34B 2024 revenue (+21.4%) with 68.9% loss ratio and 30M+ policies; Snapshot telematics and Flo brand competing with State Farm and GEICO for personal auto insurance market share.
About
Progressive Corporation is a Mayfield Village, Ohio-based property and casualty insurance company — publicly traded on the New York Stock Exchange (NYSE: PGR) as a Fortune 100 and S&P 500 company — operating as the #2 US personal auto insurer with approximately 16.7% market share, $75.34 billion in full-year 2024 revenue (+21.4% year-over-year), net income exceeding $5 billion, and an industry-leading 68.9% combined loss ratio. Progressive serves approximately 30 million policies across personal auto, commercial auto, motorcycle, boat, and homeowners insurance through both direct channels (progressive.com, call centers) and independent agent network. CEO Tricia Griffith since 2016 — the first woman to lead the company — with 50,000+ employees. Progressive was founded in 1937 by Joseph Lewis and Jack Green in Cleveland, Ohio, initially pioneering coverage for high-risk drivers that other insurers refused; the Snapshot telematics-based usage-based insurance program (launched 2011) and the Name Your Price tool revolutionized personal auto insurance pricing transparency.
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