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Obie

Insurance platform for real estate investors and landlords

Obie logo
101-200 employees
  • B2B
  • Marketplace
  • Productivity
  • Insurance
  • Real Estate
West Loop, Chicago, IL

Company mission

To make insurance for investors and landlords more transparent, simple, and cost-effective.

Top investors

Few candidates hear
back within 2 weeks

26% employee growth in 12 months

Our take

Obie serves landlords across America by providing insurance quotes for their properties. It offers an instant-quote platform that asks landlords to answer a few questions, runs an analysis based on this data and some publicly available data, and connects them with an insurance carrier that is suitable for their needs. A quote is provided, and the landlord can quickly get this underwritten.

The company is focused on a niche market of landlords with small-to-medium-size rentals. The group has been underserved by products so far, leading to poor pricing and unsuitable coverage, as well as complex and unintuitive application processes. By providing transparent and affordable insurance, the company is tackling this issue and operating in a space with few competitors.

Obie has served as an agent so far, but it's now looking at utilizing its data and clients to become its own carrier. With impressive Series B funding awarded in 2023, it is on the right track for continued success.

Steph headshot

Steph

Company Specialist at Welcome to the Jungle

Benefits

  • Parent coaching & return to work support
  • Summer hours
  • Continuing education & professional development
  • Dog friendly office
  • Life insurance
  • Medical, dental, and vision offerings
  • Stock options
  • Paid parental leave
  • Flexible PTO
  • 401K match
  • Commuter benefit plan
  • Pet insurance reimbursement
  • Flexible Spending Accounts
  • Health Savings Accounts
  • Remote & hybrid work options
  • On-site gym (Chicago location)

Company values

  • Do Good
  • Be Curious
  • Play fair
  • Stay flexible

Funding (last 2 of 5 rounds)

May 2023

$25.5m

SERIES B

May 2021

$10.7m

SERIES A

Total funding: $39.2m

This company has top investors

Leadership

Ryan Letzeiser

(CEO and Co-Founder)

They studied at Clemson University before working as a Real Estate Investment Analyst, and becoming an Investment Associate at Hudson Capital Investments. They joined MAC Properties in March 2015 as a Managing Member in 2015, before co-founding Obie in July 2018.

Aaron Letzeiser

(Co-founder)

Having spent a year as a Legislative Aide at Michigan Senate, they spent a year at ASMSU Office of Governmental Affairs before founding The Medical Amnesty Initiative. They also serve as a Managing Partner at MAC Properties, co-founding Obie with Ryan in 2018.

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