The Baldwin Group announced on January 13, 2026 that it has closed its acquisition of Obie, a Chicago‑based insurtech platform that provides embedded insurance solutions for landlords and real‑estate investors. Obie operates a digital experience that allows investors to purchase coverage directly and integrates with partner platforms to streamline underwriting and claims.
The deal expands Baldwin’s embedded insurance distribution through its Managing General Agency, Millennial Specialty Insurance (MSI), and positions the company to capture a larger share of the rapidly growing real‑estate investor market. By combining Obie’s purpose‑built technology with Baldwin’s underwriting scale and nationwide distribution reach, the company aims to offer a broader product breadth and faster, more transparent coverage for property owners.
Baldwin’s recent financial performance provides context for the acquisition. In Q3 2025 the company reported revenue of $365.4 million, up 7.8 % year‑over‑year, while its operating margin slipped from 10.2 % to 9.9 % due to higher operating expenses. The stock has declined 36.68 % over the past six months, but the acquisition is intended to accelerate growth and improve profitability by tapping Obie’s high‑growth customer base.
Obie has demonstrated remarkable growth, reporting a 2,100 % increase in revenue since 2021 and maintaining a fully reserved loss ratio below 50 %. The company has raised approximately $39 million in funding across five rounds, although its founding year is reported variably as 2013, 2017, or 2020. The platform’s success in the niche investment‑property insurance space underscores the strategic fit with Baldwin’s broader insurance portfolio.
The broader market context is favorable. The real‑estate investor insurance market is expanding quickly, and the overall property insurance market is projected to reach $37.6 trillion by 2032, growing at a 9.8 % CAGR. This growth is driven by rising real‑estate ownership, economic development, and the increasing complexity of investment vehicles, creating a tailwind for Obie’s specialized offerings.
Management emphasized the strategic value of the transaction. Amy Carlisle, President of MSI, said, “The partnership with Obie marks an important milestone in our strategy to deliver specialized insurance solutions through embedded, tech‑enabled distribution.” Jim Roche, President of The Baldwin Group, added, “Obie’s platform modernizes how landlords and real‑estate investors secure and manage coverage, and combining it with our scale positions us to better serve property owners.” Co‑founder and CEO of Obie, Ryan Letzeiser, described the deal as “a defining moment for Obie and strong validation of how venture‑backed, technology‑forward insurance distribution businesses can drive the industry forward and provide substantial returns to investors.”
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