The Baldwin Group announced it has completed the acquisition of Creisoft, Inc. and its subsidiaries, collectively known as Obie. The transaction closed on Jan. 13, 2026. Obie is a Chicago-based embedded insurance distribution business that specializes in insurance solutions for landlords and real estate investors.
The acquisition adds embedded insurance capabilities to Baldwin’s platform and expands its property distribution network across the real estate ecosystem.
Overview of the Acquisition
The Baldwin Group is an independent insurance brokerage and advisory firm that provides insurance solutions for personal and commercial clients. Through this acquisition, Baldwin adds Obie’s technology-driven insurance distribution model to its existing operations.
Obie focuses on integrating insurance into modern real estate transactions. It does so through embedded technology, a streamlined quoting experience, and a nationwide network of independent insurance agents. As a result, real estate investors can access insurance solutions directly within the platforms they already use.
Baldwin’s partnership with Obie also expands embedded insurance distribution capabilities for MSI, Baldwin’s managing general agent. In addition, the transaction strengthens Baldwin’s position in the real estate investor insurance market.
Obie’s Business Model and Growth
Obie serves landlords and real estate investors through multiple distribution channels. These include direct-to-investor digital experiences as well as integrated partner platforms. This flexible approach allows Obie to meet investors where they already operate.
At the same time, the model supports consistent underwriting standards and service quality. Since 2021, Obie has achieved revenue growth of more than 2,100 percent. During that period, the company maintained a fully reserved loss ratio below 50 percent.
Leadership Perspectives
Jim Roche, president of The Baldwin Group and CEO of underwriting, capacity, and technology solutions, said Obie has built a platform that modernizes how landlords and real estate investors secure and manage coverage. He stated that combining Obie’s technology and nationwide distribution reach with Baldwin’s scale and underwriting capabilities supports continued innovation in real estate insurance.
Ryan Letzeiser, co-founder and CEO of Obie, said the acquisition represents a defining moment for the company. He noted that joining The Baldwin Group expands Obie’s ability to offer broader products, services, and scale, while maintaining the focus and expertise of its platform.
Amy Carlisle, president of MSI, said the partnership aligns with MSI’s strategy to deliver specialized insurance solutions through embedded, technology-enabled distribution. She added that Obie has been a key distribution partner for MSI’s real estate investor program and is now part of UCTS.
About The Baldwin Group
The Baldwin Group is the brand name for The Baldwin Insurance Group, Inc. and its affiliates. The company is an independent insurance distribution firm that provides risk management, insurance, and employee benefits solutions. Baldwin represents more than three million clients in the United States and internationally and supports growth through organic and inorganic strategies.
About MSI
MSI, the brand name for Millennial Specialty Insurance, LLC, is one of the largest independent managing general agencies in the United States. MSI offers more than 20 insurance products across personal, commercial, and professional lines. Founded in 2015, MSI joined The Baldwin Group in 2019 and serves more than 1.5 million customers through its distribution partners.
Forward-Looking Statements Disclaimer
The press release includes forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. These statements reflect current expectations and beliefs and involve risks and uncertainties that could cause actual results to differ materially. The Baldwin Group does not undertake any obligation to update forward-looking statements, except as required by law.
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