About Obie
Obie is an insurtech company founded in 2017 that provides simple, affordable, and transparent insurance for landlords and real estate investors across all 50 U.S. states. Its platform uses AI and data enrichment to generate instantly bindable quotes in under five minutes for rental properties including single-family homes, multifamily buildings, and short-term rentals. Obie distributes insurance through both direct and embedded channels, integrating with proptech and fintech partners to deliver coverage seamlessly within their platforms.
Company details
Funding
Total raised
$39M
Last stage
Series B
Investors
Founders
Ryan Letzeiser
Co-Founder and CEO of Obie. Holds an MRED from Clemson University. Previously an Investment Analyst at Hudson Capital Group. Also a Managing Member at MAC Property Management.
LinkedInAaron Letzeiser
Co-Founder and COO of Obie. Brother of Ryan Letzeiser. Together they founded Obie in 2017 out of personal frustration with legacy insurance processes for real estate investors.
What happens next.
No applications, no recruiter spam. Just the intro.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.