The Baldwin Group, a Nasdaq-listed insurance brokerage based in Tampa, Florida, said on 13 January 2026 that it had completed the acquisition of Creisoft, Inc. and its subsidiaries, which do business as Obie. Obie is a Chicago-based company that sells insurance to landlords and real estate investors, often through software platforms those investors already use.
Financial terms were not disclosed. Obie will sit within Baldwin's Underwriting, Capacity and Technology Solutions unit, alongside MSI, Baldwin's managing general agent. The release said the deal widens MSI's access to embedded insurance distribution and strengthens its offering for real estate investors, a program for which Obie was already a key distribution partner.
Obie co-founder and chief executive Ryan Letzeiser called the deal a defining moment for the company and said it showed that venture-backed insurance distributors could deliver strong returns to their investors.
What Obie built
Obie was founded in 2017 to sell property and liability cover to small and mid-sized landlords who own single-family rentals or apartment buildings. When it raised its Series A in 2021, it told TechCrunch that owners could answer a short set of questions on its site and receive a quote in about three to five minutes. Its system combined the answers with public and private data and matched each property to insurers based on their appetite for different types of risk.
Over time the company leaned on partnerships. By 2023 it said it had more than 75 partners in proptech and fintech, including Baselane, Awning and Marketplace Homes, which offered Obie's insurance inside their own products. Baldwin's release said Obie now reaches investors both through its own digital channels and through integrated partner platforms.
According to the release, Obie's revenue has grown by more than 2,100% since 2021, while its fully reserved loss ratio has stayed below 50%. These are company figures and were not independently verified.
“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.”
Why Baldwin is buying
Baldwin describes itself as an independent insurance distribution firm with more than three million clients. MSI, which it bought in 2019, is one of the largest independent managing general agencies in the United States, offering more than 20 products to over 1.5 million customers.
Jim Roche, Baldwin's president and chief executive of its underwriting, capacity and technology unit, said combining Obie's technology and national reach with Baldwin's scale and underwriting would help the group serve property owners. MSI president Amy Carlisle said the company had admired Obie for some time and described the deal as a milestone in its plan to sell specialised insurance through embedded, technology-led channels.
Insurance Business reported that the Obie purchase followed Baldwin's acquisition of Capstone Group, a Philadelphia firm that expanded its presence in the Mid-Atlantic region.
The founders and the funding
Obie was started by brothers Ryan and Aaron Letzeiser, who brought backgrounds in insurance and real estate private equity, TechCrunch reported in 2021. The company went through Y Combinator.
In May 2021 Obie raised a $10.7 million Series A led by Battery Ventures, with Thomvest Ventures, FundersClub, MetaProp and Second Century Ventures taking part. Battery's Michael Brown joined the board. At the time the company said it had arranged cover for more than $3 billion of property in the previous year.
In May 2023 Battery led a $25.5 million Series B with participation from Brick and Mortar VC, DivcoWest and several real estate funds and investor groups. That round took total equity raised to about $39 million, and Obie said the property it covered had grown to more than $20 billion.
Insurance moves into software
Obie's pitch rested on the idea that landlords should be able to buy cover inside the tools they already use to finance, manage or buy property. When Battery led the Series B, Brown said the company's API-first approach of embedding its product with large partners was the right one despite volatility in real estate and insurtech markets.
For Baldwin, the purchase adds a technology-led channel to MSI's existing real estate investor program rather than building one in-house. Letzeiser said joining Baldwin would broaden Obie's products, service and scale while keeping its focus on the platform.
