Group benefits broker OneDigital has added another agency to its growing national property and casualty business. This time it's in the Chicago suburbs, and the deal leans heavily into trucking.
The Atlanta-based insurance, financial services and HR consulting firm announced on August 18 that it has brought on Midwest Insurance Agency, a 30-year-old commercial brokerage based in Elk Grove Village, Illinois. The agency gives OneDigital a bigger presence in a market it already serves, along with a specialty that's hard to build from scratch: insuring trucking fleets, owner-operators and the contractors who move freight around the Midwest.
Midwest Insurance Agency's 20-person team supports more than 1,000 clients. Its book is weighted toward commercial transportation, cargo and logistics coverage, owner-operator and independent contractor programs, contractor's insurance, and a smaller niche in home health and medical professional liability. Founder and president Tom Hammond will stay on to run the agency, which keeps its Elk Grove Village office under the OneDigital name.
Transportation risk is one of the tougher lines to underwrite well, and agencies with decades of carrier relationships in that space don't come up for sale often. Todd Belden, OneDigital's president for the Central region, credited Hammond's team with mastering "one of the most complex and specialized segments" in the P&C market. Hammond described the deal as a way to give clients access to a bigger platform without losing the "hands-on, relationship-driven service" his agency was built on.
The deal follows a pattern OneDigital has used across its Central region before, including its earlier acquisition of Watko Benefit Group under Belden. What sets this one apart is the trucking focus, arriving at a time when commercial auto risk is still one of the hardest lines in the market. Insurance Business has covered the volatility facing trucking firms heading into 2026, as tariff swings, soft freight rates and rising repair and litigation costs squeeze carriers' margins, and brokers have described how fleets are adjusting to survive the hard commercial auto market through better data, safety technology and faster claims reporting. Buying an agency with established carrier relationships in that niche gives a national broker underwriting credibility it would otherwise take years to build.
OneDigital's P&C division now serves more than 19,000 clients across all 50 states. The firm has made more than 31 acquisitions in that practice since 2021, nine of them in the Central region. Across all its practice lines — P&C, employee benefits, retirement plan services, wealth management and HR consulting — OneDigital says it has around 450 professionals working out of 35 offices in the Central US. Dowling Hales advised on the transaction, with Managing Director Harshal Gorde credited for his role in getting the deal done. Terms were not disclosed.
The deal also comes as insurance distribution keeps consolidating. OneDigital took on a new ownership structure last year when Stone Point Capital and a Canadian pension investor took a majority stake in the firm at a valuation above $7 billion, capital that helps fund exactly this kind of tuck-in deal. Private capital-backed buyers accounted for more than 70% of announced insurance brokerage M&A transactions through the first half of 2026, according to M&A advisory firm MarshBerry, even as overall deal volume has cooled a little from recent years' pace.
For Midwest Insurance Agency's clients, the practical change is likely to be small at first: same team, same relationships, now backed by a national carrier network and OneDigital's benefits, retirement and HR consulting arms.
