Obie

Insurance for landlords and real estate investors

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

Company mission

To provide a simple, affordable, and transparent insurance experience for landlords and real estate investors.

Top investors

26% employee growth in 12 months

Our take

Obie is transforming how landlords across the US access insurance for their properties. Through its tech-driven platform, landlords can easily get instant quotes, connect with the right insurance provider, and secure coverage - all without the hassle of paperwork or complicated processes. The company insures over $25M in properties across all 50 states, offering a simple and affordable alternative to traditional insurance.

Focusing on small-to-medium-sized rental properties, Obie addresses the challenges landlords face with poor pricing and inadequate coverage. By leveraging technology, the company provides customized, industry-best rates and a straightforward online experience.

With strong funding to its name and its acquisition by leading insurance brokerage The Baldwin Group, Obie is well-positioned for continued growth under new ownership, planning to reshape the future of landlord insurance.

Steph headshot

Steph

Company Specialist at Welcome to the Jungle

Benefits

  • Medical, Dental, Life, Vision
  • 401(k) Matching
  • Pet Insurance
  • Paid Parental Leave
  • Hotel Discounts
  • Telehealth
  • Flexible Time Off
  • L&D Stipend
  • Wellness Stipend
  • Benefit Support Tools

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

(Co-Founder & CEO)

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.