Matt Lossmann, Head of Distribution and Partnerships at Obie, has been named a 2026 HousingWire Rising Star — an award recognizing the next generation of leaders driving meaningful change across the housing economy.
This recognition reflects more than individual achievement. It highlights the impact of building smarter, more connected solutions for the people powering real estate investing today.
Building a Distribution Engine That Scales
When Matt joined Obie in early 2023, the agency distribution channel was still in its early stages. What followed was a rapid transformation.
In less than three years, Matt has played a large role in rebuilding and scaling the channel into a primary driver of growth, expanding access to landlord insurance across lenders, agents, property managers, and investors nationwide.
This progress didn’t come from a single partnership or shortcut. It came from a deliberate shift toward diversified relationships, operational discipline, and a deep understanding of how insurance fits into real estate transactions.
Expanding What’s Possible in the Market
Matt’s work has also helped expand participation in a part of the market that historically lacked flexibility.
By securing partnerships with leading insurance carriers and strengthening relationships across the industry, he has helped bring new capacity into the Excess & Surplus space for investment properties; opening the door for more coverage options and fewer roadblocks for investors.
That shift has a real downstream impact:
- More deals can move forward without insurance becoming a bottleneck
- Property managers and lenders can operate with greater confidence
- Investors have access to coverage designed for how they actually operate
Leadership That Drives Results
Matt’s leadership style is simple and effective: clarity, accountability, and trust.
He is known for setting clear expectations, communicating directly, and creating an environment where teams can move quickly without unnecessary friction. That approach has helped him build a high-performing team while maintaining a strong culture of ownership.
As one team member shared:
“Expectations are clear, feedback is honest, and there’s no guessing. That kind of environment makes it easier to take ownership and do your best work.”
He has also been intentional about building the right team. By recruiting high-caliber talent and empowering them to execute, Matt has created a foundation for long-term, sustainable growth.
Moving the Industry Forward
At its core, this recognition is about impact.
Matt’s work has helped position insurance as a seamless part of the real estate transaction, not a blocker. Through stronger partnerships, better alignment with lenders and property managers, and a focus on real investor needs, the distribution channel has become a meaningful lever for growth across the housing ecosystem.
And it’s still early.
Congrats to Matt on this well-deserved recognition.
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