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.
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.
SF YC W24 AI support agent builder at 80% resolution time reduction and 71% ticket deflection; $500K from a16z/Greylock/YC/Netflix competing with Intercom Fin for customer support AI workflow automation.
Duckie is a San Francisco-based AI customer support platform — backed by Y Combinator (W24) with $500,000 in funding from Y Combinator, Andreessen Horowitz, Greylock, KungHo Fund, Netflix, and 5 additional investors — providing customer support teams with an AI agent builder that translates existing support processes and workflows into predictable, reliable AI automation, achieving 80% reduction in resolution time and 71% ticket deflection for deployed teams. Founded in 2023 and targeting customer support leaders at growth-stage software companies, Duckie enables support teams to deploy AI agents in minutes without engineering dependency.
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