Matthew Lossmann has helped transform Obie’s distribution strategy, building a channel that now serves as a primary driver of the company’s growth across real estate investing and insurance. As head of Distribution and Partnerships, Lossmann leads agency development and channel partnerships that connect investors, lenders, property managers and agents with insurance solutions built for investment properties.
Over the past year, Lossmann played a central role in accelerating Obie’s reach across the housing ecosystem. Under his leadership, the company’s agency distribution channel achieved a 293% year-over-year increase in onboarded agencies and a 207% increase in agents. That growth contributed more than $100 million in incremental revenue and positioned the channel as a cornerstone of Obie’s long-term strategy.
Lossmann also secured major strategic relationships, including partnerships with two Fortune 100 insurance carriers. These agreements helped bring new capacity into the Excess and Surplus lines market for investment properties, expanding options for owners and reducing friction in real estate transactions.
His approach has centered on building a scalable organization through talent recruitment, leadership development and repeatable processes. Colleagues describe him as a transparent and decisive leader who creates clarity around expectations while empowering teams to take ownership of results.
By combining disciplined execution with a strong investment in people, Lossmann has helped Obie build a more modern, expansive insurance channel that supports real estate professionals nationwide.
What is the best piece of advice you have ever received?
My high school football coach had two sayings that have never left me: “Hard work beats talent when talent does not work hard” and “Discipline beats motivation every time.” The first taught me that what you do when no one is watching matters more than any gift you are born with. The second changed how I think entirely because motivation is a feeling and feelings fade, but discipline is a standard you hold yourself to whether you feel like it or not. Coach never gave rally speeches, he preached discipline because he knew motivation gets you started but discipline is what keeps you going. Those two lessons have shaped the way I work, the way I lead, and the way I show up every single day.
Name:
Matthew Lossmann
Age:
38
Title:
Head of Distribution and Partnerships
Company Name:
Obie
