Steadily vs Guidewire
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.
NYSE-listed (GWRE) P&C insurance core platform at $1.1B ARR serving 550+ carriers including 7 of top 10 US P&C insurers; PolicyCenter, BillingCenter, and ClaimCenter competing with Duck Creek for insurance modernization.
About
Guidewire Software is a San Mateo, California-based enterprise software company — listed on NYSE (NYSE: GWRE) — providing the core operating platform for property and casualty (P&C) insurance carriers: PolicyCenter (policy administration), BillingCenter (billing and payments), and ClaimCenter (claims management) as its Insurance Suite, alongside Guidewire Cloud, data analytics, and marketplace applications. Founded in 2001 and generating $1.1 billion in annual recurring revenue in fiscal year 2024, Guidewire serves 550+ P&C insurers globally including 7 of the top 10 US P&C carriers (State Farm, Allstate, Travelers, Liberty Mutual) and international insurers in 40+ countries.
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