Insurance Acquisitions in Kentucky
Kentucky Insurance M&A: Roll-Ups and Capabilities
Across insurance acquisitions in Kentucky, deal announcements from 2019–2026 show a steady focus on expanding brokerage footprints and deepening capabilities—particularly in employee benefits, health, and specialty lines.
A recurring theme is broker consolidation: regional and national platforms such as Afore Insurance Services, Hub International Limited, The Hilb Group, Inszone Insurance Services, and Highstreet Insurance Partners have acquired Kentucky agencies or insurance-related businesses in locations including Louisville, Lexington, Paducah, and Simpsonville.
Several transactions also highlight capability expansion beyond traditional agency sales—such as third-party administration and managed care (Charles Taylor acquiring Underwriters Safety & Claims (US&C)) and employer solutions (e.g., Risk Strategies acquiring HollandStivers Employer Solutions). Financial terms were not disclosed for most deals.
What Stands Out
- Kentucky roll-ups span multiple city hubs—Louisville, Lexington, Paducah, and Simpsonville appear across recent transactions.
- Buyer activity is dominated by brokerage platforms and roll-up operators, including Hub International Limited, The Hilb Group, Inszone Insurance Services, Highstreet Insurance Partners, and Risk Strategies.
- Capability themes include group employee benefits and health/Medicare advisory (e.g., Afore Insurance Services, PCF Insurance Services), plus employer solutions with payroll/HCM/HR services (Risk Strategies).
- Some deals target adjacent services: Charles Taylor’s acquisition of US&C expands claims management and managed care services.
| Buyer platform | What the deal adds (as described) | Kentucky footprint signal |
|---|---|---|
| Afore Insurance Services | Group employee benefits capabilities; local team | New Louisville-area office |
| Inszone Insurance Services | Local franchise + carrier access while preserving relationships | Lexington market entry |
| Risk Strategies | Payroll administration, HCM implementation, HR services | Kentucky expansion of National Employee Benefits |
| Charles Taylor | U.S. claims management and managed care capabilities | Southeast/Midwest footprint broadening |
-
February 9, 2026
- Buyer
- Afore Insurance Services
- Target
- Myron K. Hobbs & Company, LLC
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Addon
Afore Insurance Services has acquired Myron K. Hobbs & Company, LLC, marking Afore’s entry into Kentucky and establishing a new Louisville-area office. The acquisition brings group employee benefits capabilities and the Myron Hobbs team into Afore’s platform; financial terms were not disclosed.
-
September 16, 2025
- Buyer
- Inszone Insurance Services
- Target
- Lexington Insurance Agency
- Seller
- Kevin O. Stinnett
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
Inszone Insurance Services acquired Lexington Insurance Agency, an independent insurance agency based in Lexington, Kentucky, marking Inszone's entry into the Kentucky market. The deal brings Lexington's ~11 employees and 70+ year local franchise under Inszone's national brokerage platform to expand geographic reach and carrier access while preserving local relationships.
-
- Buyer
- The Hilb Group
- Target
- Kentucky-based multi-line insurance agency (unnamed)
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Addon
The Hilb Group, a Richmond, Virginia-based property & casualty and employee benefits brokerage, has acquired a Kentucky-based multi-line insurance agency effective July 1, 2025. The deal adds Kentucky to Hilb Group's footprint as part of its ongoing roll-up strategy as a Carlyle-backed platform.
-
- Buyer
- PCF Insurance Services
- Target
- Kentucky Health Solutions (insurance business)
- Seller
- Kentucky Health Solutions
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Addon
PCF Insurance Services, a top-20 U.S. insurance brokerage headquartered in Lindon, Utah, has acquired the insurance business of Kentucky Health Solutions in Lexington, Kentucky. The Kentucky Health Solutions team will join PCF’s Louisville-based Maverick Insurance Group to expand local service offerings and deepen PCF’s health, life and Medicare advisory capabilities in the region.
-
August 14, 2024
- Buyer
- MEM Capital LLC
- Target
- Mountain Life Insurance Company, Kentucky Home Life Insurance Company
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
MEM Capital LLC of Greenwich, Connecticut has acquired Mountain Life Insurance Company and Kentucky Home Life Insurance Company; both carriers will continue to maintain their home offices and management team in Lexington, Kentucky. Mountain Life plans to begin offering annuity products, Jeff Breeze will remain President, and Benjamin Keslowitz will join as Board Chairman.
-
- Buyer
- Highstreet Insurance Partners
- Target
- RISE Partners
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Addon
Highstreet Insurance Partners, a Traverse City, Michigan-based independent insurance brokerage, has acquired RISE Partners, a Louisville, Kentucky insurance agency. The deal (terms undisclosed) expands Highstreet’s footprint into Kentucky while RISE’s founder Mike Arnold will continue to lead the business under Highstreet’s ownership.
-
April 18, 2023
- Buyer
- Risk Strategies
- Target
- HollandStivers Employer Solutions
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
Risk Strategies, a national specialty insurance brokerage, has acquired HollandStivers Employer Solutions, an employee benefits specialist based in Paducah, Kentucky. The acquisition (terms undisclosed) expands Risk Strategies' National Employee Benefits Practice into Kentucky and adds HollandStivers' payroll administration, HCM implementation and HR services capabilities.
-
October 4, 2022
- Buyer
- Hub International Limited
- Target
- Peel & Holland Holdings, Inc., Peel & Holland, Inc., Riddle Insurance, LLC, Hartin Dynamics, LLC, Bluegrass Premium Finance, LLC
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
Hub International Limited has acquired the assets of Peel & Holland (including Peel & Holland Holdings, Peel & Holland, Inc., Riddle Insurance, Hartin Dynamics, LLC, and Bluegrass Premium Finance, LLC). The transaction, terms undisclosed, brings the Peel & Holland leadership and team into Hub Mid-South and expands Hub’s commercial, personal insurance and employee benefits capabilities across Western Kentucky.
-
- Buyer
- One80 Intermediaries
- Target
- National Insurance Agency of Simpsonville
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
One80 Intermediaries, a Boston-based specialty insurance broker, has acquired National Insurance Agency of Simpsonville, a Kentucky-based broker that provides life and occupational disability insurance to professional associations. The acquisition expands One80's affinity-focused insurance capabilities and geographic reach in Kentucky and Arkansas; terms were not disclosed.
-
January 5, 2022
- Buyer
- Charles Taylor
- Target
- Underwriters Safety & Claims (US&C)
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
Charles Taylor has acquired Underwriters Safety & Claims (US&C), a Louisville-based third-party administrator and managed care services provider. The acquisition expands Charles Taylor’s U.S. claims management and managed care capabilities and broadens its geographic footprint into the Southeast and Midwest.
-
- Buyer
- AssuredPartners, Inc.
- Target
- Rice Insurance Services Company, LLC
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
AssuredPartners, Inc. has acquired Rice Insurance Services Company, LLC (RISC) of Louisville, Kentucky. The 27-person agency, which generates approximately $6 million in annualized revenue and specializes in real estate E&O programs, will join AssuredPartners to expand the firm’s presence and capabilities in Kentucky.
-
December 2, 2020
- Buyer
- Marsh & McLennan Agency LLC (MMA)
- Target
- Heritage Insurance Service, Inc.
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
Marsh & McLennan Agency LLC (MMA), the middle-market agency subsidiary of Marsh, has acquired Heritage Insurance Service, Inc., an independent insurance agency based in Louisville, Kentucky. Heritage, which has about 30 employees across five locations and specializes in trucking and transportation insurance, will join MMA to expand MMA's specialty capabilities and client reach.
-
November 9, 2019
- Buyer
- Arthur J. Gallagher & Co.
- Target
- Garrett-Stotz Company
- Industry
- Insurance
- Location
- Kentucky, United States
- Type
- Buyout
Arthur J. Gallagher & Co. (Gallagher) has acquired Garrett-Stotz Company, a Louisville, Kentucky-based full-service commercial and personal lines property/casualty and benefits agency founded in 1931. The deal expands Gallagher’s presence in Kentucky and Indiana, adds expertise in construction and surety, and creates cross-selling opportunities across Gallagher’s retail insurance and employee benefits operations; terms were not disclosed.
Track M&A activity that matters to you
Get real-time deal alerts, build buyer lists with AI, and access our full acquisition database. Start your free trial today.
Frequently Asked Questions
Which types of insurance firms are most active in Kentucky acquisitions?
Brokerage platforms and specialty insurance operators are prominent, including firms focused on property & casualty and employee benefits, as well as specialty brokers that expand through acquisitions of agencies and insurance-related businesses.
What Kentucky cities show up most often in the deal announcements?
Recent listings reference acquisitions connected to Louisville, Lexington, Paducah, and Simpsonville.
Do any Kentucky deals involve more than traditional insurance agency operations?
Yes. For example, Charles Taylor acquired Underwriters Safety & Claims (US&C), a third-party administrator and managed care services provider, and Risk Strategies acquired an employer benefits specialist with payroll administration and HCM implementation capabilities.
Were purchase prices disclosed in these Kentucky insurance acquisitions?
For most of the listed transactions, the summaries state that financial terms were not disclosed.