The Baldwin Group acquires Obie
The Baldwin Group has completed the acquisition of Obie, a Chicago-based startup offering insurance solutions for landlords and real estate investors.

Obie serves real estate investors through multiple distribution channels, including direct-to-investor digital experiences and integrated partner platforms. Baldwin’s partnership with Obie expands access to embedded insurance distribution capabilities for MSI, Baldwin’s managing general agent and strengthens its offerings in the real estate investor market.
Founded in 2017, Obie publicly disclosed $39 million in funding.
“Obie has built an impressive investment property insurance platform that modernizes how landlords and real estate investors secure and manage coverage. By combining Obie’s purpose-built technology and nationwide distribution reach with our scale and underwriting capabilities, we are well positioned to better serve property owners and continue driving innovation across the real estate insurance market.” – Jim Roche, President, The Baldwin Group and CEO, Underwriting, Capacity, and Technology Solutions.
“This is a defining moment for Obie and strong validation of how venture-backed, technology-forward insurance distribution businesses can both drive the industry forward and provide substantial and outsized returns to investors. Becoming part of The Baldwin Group expands what we can offer the market, from product breadth to service and scale, while preserving the focus and expertise that define our platform. It positions Obie to play a much larger role in how insurance is distributed across the ecosystem.” – Ryan Letzeiser, Co-founder and CEO of Obie.
“The partnership with Obie marks an important milestone in our strategy to deliver specialized insurance solutions through embedded, tech-enabled distribution. As a key distribution partner for MSI’s real estate investor program today, we have admired Obie for quite some time now and are thrilled to welcome them to UCTS.” – Amy Carlisle, President of MSI.
