Steadily, a landlord insurance provider operating in all 50 U.S. states has launched a new app within ChatGPT that allows property owners to receive instant insurance premium estimates. The company says it is the first U.S. insurance provider focused exclusively on landlord insurance to offer quotes through a ChatGPT app.
The new feature allows landlords to estimate insurance costs directly within the same AI conversations they may already use to analyze potential real estate investments.
AI Integration Expands Insurance Access
Steadily introduced the ChatGPT app as AI tools become more common among property investors. Many landlords now rely on AI to analyze deals, evaluate rental markets, and model cash flow. The company designed the app to integrate insurance cost estimates into those existing workflows.
As a result, landlords can estimate insurance expenses without leaving the ChatGPT interface. According to Steadily, this approach allows users to evaluate property performance and insurance costs in one conversation.
Steadily is among the first U.S. insurance providers to bring its quoting experience into an AI-native platform. It is also the first provider dedicated specifically to landlord insurance to offer this capability through ChatGPT.
How the ChatGPT App Works
Landlords can access the quoting tool by connecting the Steadily app within ChatGPT. After the app is connected, users request an insurance quote by entering basic property details. The process begins with the property address.
Next, the system retrieves relevant information from Steadily’s underwriting engine. This data includes square footage, year built, and other property characteristics. The system then generates an estimated monthly premium within seconds.
The estimate appears directly in the conversation alongside the property details and projected monthly cost. From there, users can continue to Steadily’s full quoting platform to finalize coverage.
Industry Response to Changing Workflows
Steadily leadership says the new tool responds to how landlords are already using AI in their investment decisions.
“Property investors are already using AI to analyze deals, evaluate rental markets, and model cash flow,” said Darren Nix, CEO and co-founder of Steadily. “With our ChatGPT app, landlords can now estimate insurance costs in the same conversation where they’re evaluating a property, removing another layer of friction from protecting their investments.”
The company says the launch also reflects a broader trend of financial services integrating directly into AI-driven workflows. With Steadily’s quoting technology embedded in ChatGPT, landlords can analyze deals, estimate rental income, and evaluate insurance costs in a single conversation.
About Steadily
Founded in 2020, Steadily provides specialized insurance services for real estate investors and property owners. The company offers property and liability coverage across all 50 U.S. states through a technology-driven platform that provides fast online quotes and flexible coverage options.
Steadily offers insurance for several rental property types, including long-term rentals, short-term vacation rentals such as Airbnb and VRBO properties, single-family homes, multi-family properties, condominiums, and properties undergoing renovation.
More information is available at www.steadily.com.
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