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Obie

Obie

Private
Chicago, IllinoisFinTechhttps://www.obieinsurance.com/

Last Round

Series B

May 17, 2023

Total Funding Raised

$41.8M

Momentum

Top 25%

of companies Caplight tracks

Company Overview

Obie is an insurance technology company that provides a digital platform for landlords and real estate investors to manage property insurance and risk.

Sector

FinTech

Verticals

InsurTech, Property Investment, Property Management

Business Model

B2B

Customer Profile

Payment Processing Fee

AI Layer

Application

Keywords

insurtechlandlord insuranceinvestment property insurancedigital insurance platformembedded insuranceinsurance brokerageproperty insuranceinsurance automationreal estate insuranceproptechinsurance APIonline insurance quotesinsurance marketplacedigital brokerageinsurance tech

Historical Pricing

Historical view of private secondary pricing and transaction trends.

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Caplight Momentum Score

Proprietary index based on bid/ask volume and sentiment.

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Obie Comparables

Compare Obie with similar companies based on industry and business-model similarity.

Obie comparables — related companies by embedding similarity
CompanySimilarityMarket Cap
Steadily
93%
Honeycomb Insurance
86%
National Real Estate Insurance Group
81%

Obie Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
Series BMay 17, 2023
Series AMay 26, 2021
SeedNov 19, 2019
SeedOct 1, 2019

Key People

Founding team and executive leadership

Ryan Letzeiser

Co-Founder & CEO (Y Combinator S19)

Founding Team

Curtis Jackson

Chief Technology Officer

Executive Team

Obie Investors

Notable investors and investment history

Obie investors
InvestorRounds
Second Century VenturesSeries A
Pioneer FundSeed
DivcoWestSeries B
MetaPropSeed, Series A
Battery VenturesSeries B, Series A
Y CombinatorSeed
Soma CapitalSeed

Market signals

Structured signals derived from secondary market and firmographic data.

  • Mar 1, 2026

    Listed on the Inc. 5000 fastest-growing companies.

  • Mar 1, 2026

    Recognized as a top workplace by Built In and Inc.

Recent news

Latest coverage and updates

  • partners_withAug 25, 2026

    Obie Insurance Group partnered with RentSpree on Aug 25th '26.

Obie Filings

Explore SEC and related filing metadata, where available.

Obie filings preview — column headings only; records require access
TypeDateAmount OfferedAmount SoldFilingPagesDownload

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Frequently Asked Questions

Common questions about Obie's valuation, stock price, and market status.

Is Obie a public or private company?

Obie is a private company.

What is the current stock price of Obie?

Obie is a private company with no public stock price. No recent secondary market data is available.

How much is Obie worth (valuation)?

Valuation information for Obie is not publicly available.

Can I buy Obie stock?

Obie shares may be available on secondary markets subject to transfer restrictions. Caplight facilitates secondary market transactions for accredited investors. Visit https://www.caplight.com to learn more.

When was Obie's last funding round?

Obie's most recent funding round was Series B on May 17, 2023.

Who are the main investors in Obie?

Key investors in Obie include Battery Ventures.

Will Obie IPO soon?

No public IPO plans have been announced for Obie.

How can I track Obie secondary market activity?

Caplight tracks bids, offers, and trades for private companies. Visit https://www.caplight.com to monitor Obie's secondary market activity and sign up for updates.

Firmographic Details

HeadquartersChicago, Illinois
Employee Range100
Year Founded2017
Last FundingMay 17, 2023

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