Obie logo

Obie

Brand · Insurance

Company overview

Meet the new standard in landlord insurance. Obie is an insurance technology solution designed exclusively to meet the needs of the modern real estate investor. With Obie, you can request a quote in under 5 minutes–meaning no more tedious paperwork and lengthy wait times.
Founded in 2017
Chicago, Illinois, USA
163 employees (17 in marketing)
www.ObieInsurance.com

Salaries

Typical salary range

$70,000 – $95,000

/ yr

Help build salary transparency at Obie

Share your compensation anonymously to see full data.

Contribute

People

Founders and leadership

Ryan Letzeiser
Ryan Letzeiser
Co-Founder & CEO (YC S19) - Acquired Jan 2026 (BWIN - Nasdaq)
At the company for 8 years 2 months
Aaron Letzeiser
Aaron Letzeiser
Co-Founder
At the company for 8 years 3 months

Marketing leadership

Jessica Smith
Jessica Smith
Director of Marketing
At the company for 2 years 4 months
Carolyn Jackson
Carolyn Jackson
Marketing Manager
At the company for 2 years 5 months
Ariel Kirschner
Ariel Kirschner
Lead Marketing Executive
At the company for 2 years 8 months

Hiring contacts

Mary Kaufhold
Mary Kaufhold
People Ops Coordinator
At the company for 4 years 10 months
Skylar Hanson, SHRM-CP
Skylar Hanson, SHRM-CP
People Operations Generalist
At the company for 1 year 7 months

Hiring activity

Open marketing jobs over time

1 open now

Headcount trend

Company growth over the last 12 months

Headcount 0% year over year

Funding

Total funding

$39M

Last raise

$25.5M

Series B, 3 years ago

Funding history

May 2023

Series B Obie · $25.5M

May 2021

Series A Obie · $10.7M

Sep 2019

Seed Round Obie · $2.7M

Jan 2017

Pre Seed Round Obie · $150K

Audience

Monthly website visitors
69.5K
Month over month-9.7%
Quarter over quarter+22%
Top sourceDirect (67.1%)
Ad budget per month$38.6K
Average search rank36.3
Traffic source mix
Direct
67.1%
Search
26.1%
Referral
5.9%
Paid referral
0.6%
Social
0.2%

LinkedIn followers

Follower count and growth

Total followers

6.8K

12-mo growth

+28.6%

Monthly growth

+1.7%

News

Links

www.ObieInsurance.comLinkedInCrunchbaseX (Twitter)