Harper vs Progressive
Side-by-side comparison of AI visibility scores, market position, and capabilities
Raised $47M combined seed + Series A (Feb 2026) led by Emergence Capital. YC W25. 5,000+ customers. Largest publicly disclosed Series A by a Black founder. Mostly autonomous licensed commercial insurance agency.
About
Harper is an AI-native commercial insurance brokerage that is nearly fully autonomous — matching SMBs to coverage across 160+ carriers, routing quotes, processing documents, and following up with underwriters without requiring human broker involvement for most transactions. The company raised $47 million across seed and Series A financing in February 2026 led by Emergence Capital, following its Y Combinator W25 graduation. Harper serves 5,000+ customers and represents the largest publicly disclosed Series A by a Black founder.
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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