Steadily vs Progressive
Side-by-side comparison of AI visibility scores, market position, and capabilities
Austin landlord insurance insurtech at $250M+ annualized GWP; $89.5M total ($30M Two Sigma Series C April 2025 at $355M) with Inc. 5000 #63/4,606% growth and own carrier launch Q4 2024 competing with Obie for individual landlord insurance.
About
Steadily is an Austin, Texas-based insurtech specializing exclusively in landlord insurance — backed with $89.5 million in total funding including a $30 million Series C in April 2025 led by Two Sigma Ventures at a $355 million valuation — providing America's 18 million individual rental property owners with fast, mobile-first insurance quotes for single-family rentals, multi-family units, condos, ADUs, short-term rentals (Airbnb/VRBO), and small apartment buildings in all 50 states, with $250+ million in annualized gross written premium. Inc. 5000 ranked Steadily #63 in 2025 with 4,606% three-year revenue growth. Steadily integrates with 400+ proptech platforms including Roofstock, TurboTenant, FurnishedFinder, and BiggerPockets. In Q4 2024, Steadily launched its own insurance carrier (Steadily Insurance Company), vertically integrating from MGA/distribution to risk-bearing carrier. Founded 2020 by landlords Darren Nix (CEO), Datha Santomieri, and David Tulig who experienced the limitations of the existing landlord insurance market firsthand.
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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