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Obie

Obie

Private
Chicago, IllinoisFinTechhttps://obieinsurance.com

Last Round

Series B

May 17, 2023

Total Funding Raised

$39M

Momentum

Top 25%

of companies Caplight tracks

Company Overview

Obie operates in FinTech and is based in Chicago, Illinois. Its latest recorded funding round was a Series B round in May 2023.

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, Real Estate Finance

Business Model

B2B

Customer Profile

Payment Processing Fee

AI Layer

Application

Historical Pricing

Historical view of private secondary pricing and transaction trends.

Pricing history

Caplight clients see full MarketPrice™ history and secondary transactions.

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Caplight Momentum Score

Proprietary index based on bid/ask volume and sentiment.

Momentum history

Caplight clients track how buyer interest and sentiment change over time.

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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
89%
Honeycomb Insurance
86%
National Real Estate Insurance Group
83%
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Obie Funding Rounds

Historical fundraising activity

Data table
RoundDateAmount RaisedValuationInvestorsSources
Series BMay 17, 2023
Series AMay 26, 2021
SeedNov 19, 2019
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Key People

Founding team and executive leadership

Ryan Letzeiser

Co-Founder & CEO (Y Combinator S19)

Founding Team

Curtis Jackson

Chief Technology Officer

Executive Team

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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
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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.

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Recent news

Latest coverage and updates

  • partners_withAug 25, 2026

    On Aug 25th '26 in Illinois, Obie Insurance Group and RentSpree announce a partnership that gives RentSpree users direct access to Obie Insurance Group's landlord insurance experience, including real-time quotes and coverage purchases within the platform.

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Obie Filings

Explore SEC and related filing metadata, where available.

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

Filing documents are not displayed on this public page. Request access to learn about available coverage.

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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, so its shares have no public market price. Caplight tracks Obie's secondary market activity and provides MarketPrice™ estimates of its share price to Caplight users.

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.

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 in Obie's shares on secondary markets.

Firmographic Details

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

Institutional Data Access

Join leading institutional investors using Caplight to access private market data, discover pricing, and execute secondary block trades.

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