Steadily
Steadily sells landlord insurance online, underwritten by its own A-rated carrier.
On the record
Checkpoint: First full catastrophe and reinsurance cycle test for Steadily's 18-month-old carrier
The call
Steadily has a real regulated carrier and fast growth, but Openly is bigger and better funded in the same lane, and Steadily's own book hasn't been tested by a real disaster cycle yet.
Steadily sells renters and landlord insurance online by owning its own insurance company, which requires expensive government licenses that slow down competitors. However, Openly is a similar company that has raised more money and is already larger, and old-school insurers like State Farm and Allstate are not truly blocked from selling online the same way. The biggest question is whether Steadily's partnerships with property managers and lenders will keep customers loyal, or if AI-powered comparison websites like Insurify will let customers shop around so easily that Steadily loses its advantage.
Why
01
AI pressure: Insurify, Jerry, ChatGPT-style quote aggregators. AI chatbots and aggregators could grab the quote-comparison step, but they still hand off to a regulated carrier to actually write the policy. Could AI do the core job? Only partly.
02
Bigger players: Openly. Openly has raised about $430M, is valued over $1B, and already leads the landlord/DTC niche Steadily is chasing. Could a giant copy it? Probably.
03
What protects it. Its own Demotech A-rated carrier and state licenses make copying the underwriting slow, even though nothing legally blocks a rival from doing it.
What would change this call
Steadily's own carrier reports loss ratios after a hurricane or wildfire season. Shows whether its underwriting can survive a real catastrophe cycle.
Openly discloses GWP or valuation growth that widens the gap over Steadily. Confirms Openly extending its lead in the same landlord insurance niche.
A major insurer like Progressive or Travelers launches a direct-to-consumer landlord policy. Would show incumbents finally closing the DTC gap Steadily exploited.
Openly discloses GWP or valuation growth that widens the gap over Steadily. Confirms Openly extending its lead in the same landlord insurance niche.
A major insurer like Progressive or Travelers launches a direct-to-consumer landlord policy. Would show incumbents finally closing the DTC gap Steadily exploited.
Key numbers
- $300M+ gross written premium
- $89.5M total funding raised
- 100,000+ landlords served
Named risks
- Own carrier (Steadily Insurance Company) has no loss-cycle track record since first policy in Nov 2024.
- AI quoting aggregators (Insurify, Jerry.ai) could commoditize the DTC front-end funnel.
- Larger, better-funded rival Openly leads the landlord insurance category as of 2025.
- Property insurance sector faces climate/catastrophe and reinsurance cost volatility industry-wide.
- ChatGPT-native distribution unproven; July 2026 industry commentary flagged poor chat-to-bind handoff.
Rivals, as read in July 2026
| Rival | Direction | Evidence |
|---|---|---|
| Openly | losing to | Larger, better-funded landlord/homeowners insurer with higher reported valuation as of April 2025 |
| Obie | contesting | Chicago-based embedded insurance rival for real estate investors, claims over $4B insured assets |
| State Farm, Allstate, Travelers, Safeco/Liberty Mutual, Farmers | gaining on | Slow-moving incumbents still dominate landlord/dwelling-fire policies through agent networks as of 2026 |
| Insurify, Jerry.ai, Experian's Gabi, Neptune Flood | contesting | Rival ChatGPT-native insurance quoting apps shipped in same Feb-March 2026 window as Steadily's |
Questions people ask
- Is Steadily profitable in 2026?
- No public profitability figures have been disclosed. Steadily reports over $300M gross written premium as of August 2025 and raised a $30M Series C in April 2025 at a $355M valuation, but net income or margin data is not published.
- Who owns Steadily?
- Steadily is a private, venture-backed company founded in 2020 by Darren Nix, Datha Santomieri, and David Tulig. Investors include Matrix Partners, Zigg Capital, and Two Sigma Ventures. Total funding reached $89.5M after its April 23, 2025 Series C. No acquisition has occurred.
- Is Steadily bigger than Openly?
- No. Openly, a Boston-based landlord/homeowners insurer, has reportedly raised far more capital and reached a valuation exceeding $1B, while Steadily's Series C in April 2025 valued it at $355M with over $300M GWP by August 2025.
- Could AI replace Steadily?
- AI can replicate Steadily's front-end quoting, which is why Steadily launched a ChatGPT app on March 16, 2026, joining Insurify and Jerry.ai. But AI cannot replace its licensed, Demotech A-rated carrier or regulatory underwriting infrastructure.
- How much funding has Steadily raised?
- Steadily has raised $89.5M total as of April 23, 2025, across a $3.8M seed (2020, Matrix Partners), a Series A bringing the total to $31M by November 2021, a $28.5M Series B (July 2023, Zigg Capital), and a $30M Series C (Two Sigma Ventures) at a $355M valuation.
- Does Steadily have its own insurance carrier?
- Yes. Steadily Insurance Company activated as an admitted carrier and issued its first bound policy in November 2024, earning a Demotech 'A, Exceptional' financial stability rating the same month, alongside five MGA programs and a large agency arm.
Timeline
- 2026-03-16Launched dedicated ChatGPT app for instant landlord insurance premium estimates
- 2025-08Ranked No. 63 on 2025 Inc. 5000 list; GWP surpasses $300M
- 2025-04-23Raised $30M Series C led by Two Sigma Ventures at $355M valuation, total funding $89.5M
- 2024-11-21Steadily Insurance Company earns Demotech 'A, Exceptional' rating, issues first bound policy
- 2023-07-05Raised $28.5M Series B led by Zigg Capital, total funding ~$59M
- 2021-11Series A raise brings total funding to $31M
- 2020Founded by Darren Nix, Datha Santomieri, David Tulig; raised $3.8M seed led by Matrix Partners
Revision history
23 July 2026
First assessed. Losing its protection. The text above is fixed as of this date and is not edited afterwards.
In the same band
Sources
- Steadily Comes Out of Stealth with $3.8 Million...
- Steadily Secures $30M Series C...
- Steadily Raises $31 Million...
- Steadily Raises $28.5 Million... (2023-07-05)
- Steadily Secures $30M Series C... (2025-04-23)
- Steadily raises $30 million (2025-04-25)
- Steadily Ranks No. 63 on the 2025 Inc. 5000 List
- Demotech Assigns A Rating to Steadily Insurance Company (2024-11-21)
- Steadily Insurance Company - Headcount... (2026-07-13)
- Steadily and RLI Partner...
- Steadily Launches First-of-Its-Kind Landlord Insurance App on ChatGPT (2026-03-16)
- Neptune Flood, Steadily, and Jerry.ai Offer Instant Quotes