Steadily Builds Digital Insurance Platform Around America’s Landlords

Founded in 2020, Steadily has built a specialist insurance business around rental property owners, combining digital distribution with nationwide licensing, its own insurance carrier and a growing network of real estate technology partnerships.

Steadily has spent the past six years building an insurance business around a specific customer: the rental property owner. Founded in 2020 by Darren Nix, Datha Santomieri and David Tulig, the company specializes in landlord insurance, aiming to replace a traditionally cumbersome purchasing process with faster digital quoting and coverage designed specifically for investment properties. The business has grown beyond its startup origins into a nationally licensed insurance operation backed by $89.5 million in disclosed funding, including a $30 million Series C announced in April 2025.

The approach reflects a broader shift in insurance technology: rather than attempting to serve every insurance category, Steadily has concentrated on a relatively narrow segment and built its technology, underwriting and distribution strategy around the needs of property investors.

Building Insurance Specifically for Rental Properties

Steadily’s founding premise came partly from Nix’s own experience as a property investor. According to the company, the idea emerged after he encountered difficulties obtaining insurance for his first rental property. He later became Steadily’s first customer after the business launched.

That experience helped define the company’s focus.

Landlord insurance differs from standard homeowners insurance because rental properties create distinct exposures, including landlord liability and potential loss of rental income. Steadily offers coverage for property types including single-family and multifamily rentals, condominium units, accessory dwelling units, vacant or restoration properties and short-term rentals.

Its digital model is designed to let property investors obtain coverage quickly rather than relying entirely on the traditional back-and-forth between customers, agents and insurers.

The company’s insurance infrastructure has also expanded. Steadily Insurance Agency is licensed in all 50 U.S. states and Washington, D.C., while Steadily Insurance Company is an Arizona-domiciled insurer with NAIC number 16963. Both are wholly owned subsidiaries of Steadily Inc.

That structure means Steadily is no longer simply a technology layer connecting customers with third-party insurance products; it has developed insurance-carrier capabilities alongside its agency and distribution operations.

Nearly $90 Million in Funding Backs Steadily’s Expansion

Capital has played an important role in that development.

Steadily emerged from stealth in 2020 with $3.8 million in seed financing led by Matrix Partners. In 2021, the company announced additional investment that brought its total funding at the time to $31 million, with Matrix Partners and Zigg Capital leading the new financing.

A $28.5 million Series B followed in 2023, led by Zigg Capital and joined by investors including Matrix Partners, Koch Real Estate Investments, Clocktower Technology Ventures and Nine Four Ventures.

Steadily’s next major financing came in April 2025, when it announced a $30 million Series C led by Two Sigma Ventures at a stated valuation of $355 million. Zigg Capital, Clocktower Technology Ventures, Belfer Investment Partners, Nine Four Ventures and Matrix Partners also participated. The financing brought total funding announced by the company to $89.5 million.

At the time of the Series C, Steadily said it had surpassed $250 million in annualized gross written premium. The company also said it had integrated with more than 400 businesses, including property and real estate platforms, as it increasingly used embedded distribution to put insurance estimates closer to the point where investors evaluate or manage properties.

Partnerships Extend Steadily Beyond Direct Insurance Sales

Distribution has become another important part of Steadily’s model.

Rather than relying solely on customers visiting its website for insurance, the company has integrated insurance into platforms used elsewhere in the property investment process.

In March 2026, Steadily announced a partnership with BiggerPockets under which it became the landlord insurance provider for the real estate investing platform’s Pro Perks program. BiggerPockets says its community includes more than three million real estate investors.

Steadily has also been developing additional routes to market through insurance agents and brokers. In June 2026, it announced a distribution partnership with specialty insurer RLI intended to expand nationwide access to landlord insurance through appointed agents and brokers.

The combination of direct digital sales, embedded insurance partnerships and agency distribution gives Steadily multiple channels through which to reach property investors.

Technology Moves Closer to the Investor’s Workflow

Steadily has continued experimenting with how insurance is accessed as property investors adopt new digital tools.

In March 2026, the company launched a ChatGPT app that allows users to request rental-property insurance premium estimates from within ChatGPT. Users can begin the process with a property address rather than moving first to a conventional insurer website.

The development fits a longer-running strategy. Steadily has previously offered embedded insurance capabilities to property technology businesses, allowing insurance estimates or services to appear inside platforms that investors already use.

For Steadily, the opportunity is therefore broader than digitizing an insurance application. Its strategy increasingly centers on placing landlord insurance inside the wider technology ecosystem used to find, finance and operate rental properties.

Six years after its founding, that focused approach has produced a specialist insurance company with nationwide agency licensing, its own carrier, substantial venture backing and multiple digital distribution channels.

The longer-term test will be whether specialization and technology can continue translating into durable scale in a highly regulated insurance market. Steadily’s development so far shows how a narrowly defined customer problem — insuring rental properties — can become the foundation for a broader insurance and distribution platform.