Best Commercial Fleet Insurance Agencies for Commercial Vehicles: 2026

Between May and September 2026, our research team evaluated Midwest-based agencies and brokers that place commercial fleet insurance for commercial vehicles, scoring each on a weighted seven-factor model built from agency websites, industry rankings, trade announcements, and public review platforms. Below is the full methodology broken out.

• Digital Self-Service and 24/7 Coverage Access (20%): Commercial vehicles run on schedules that ignore office hours, so we weighted client portals, online certificate and claim requests, and coverage that can be added outside the business day.
• Upper Midwest Presence and Multi-State Licensing (20%): Fleets based in Minnesota, Wisconsin, Iowa, and the Dakotas benefit from an agency with local offices and regional market knowledge that is also licensed for the states their vehicles travel through.
• Direct Agent and Leadership Access (20%): When a claim or renewal goes sideways, the ability to reach a named agent or a company leader directly shortens the path to a resolution.
• Year Founded (10%): Longevity in commercial vehicle insurance signals carrier relationships that hold up through hard insurance markets.
• Average Review Score (10%): Client reviews show how an agency treats fleets after the policy is bound.
• Price Range (10%): We rated each agency from $ to $$$$$ based on how flexible its pricing is across fleet sizes, budgets, and carrier options, with $ being the least flexible and $$$$$ being the most flexible.
• Awards and Recognition (10%): Industry awards, rankings, and partner designations offer third-party validation of an agency’s standing.

The Best Commercial Fleet Insurance Agencies for Commercial Vehicles in 2026

1. Truck Writers, for 24/7 Self-Service and Direct Agent Access

Donald and Bonnie Sullivan opened their Minnesota agency in 1983. In 1984, they moved it away from general insurance and into transportation. That focus has held for more than four decades. The family still owns and runs the agency. Shawn Sullivan is CEO, and Mackenzie (Sullivan) Thompson is COO. Truck Writers now ranks among the largest truck insurance agencies in the Midwest. Each fleet client works with its own account team, backed by a dedicated support team. Because it is independent, the agency compares options from carriers such as Great West Casualty, National Indemnity, Northland, Progressive, Travelers, Canal, Great American, and Acuity.

Where Truck Writers separates itself is how easy it is to reach, both online and by phone. Fleet clients can pull policy documents through a client portal, pay bills online, request certificates, and report claims without waiting on a callback, and the agency’s self-service per trip excess liability and cargo coverage can be purchased at any hour, any day of the year. When a situation calls for a person, the agency publishes direct phone lines and email addresses for its CEO, vice presidents, and agents, a level of access that is uncommon among firms its size. Offices in Blaine and rural Welcome, Minnesota anchor its service to fleets in Minnesota, Wisconsin, Iowa, North Dakota, and South Dakota, while primary trucking coverage in 13 states (and non-trucking and bobtail coverage in 38 states) supports vehicles that run well beyond the region. The agency also serves as a licensed third-party administrator for a transportation captive and a self-insured workers’ compensation program.

Location: Blaine, MN (additional office in Welcome, MN)

Founded: 1983

Avg. Review Score: 4.5/5.0 (Google, 28 reviews, accessed October 2026)

Price Range: $$$$$

Services: Auto liability, physical damage, motor truck cargo, workers’ compensation, freight broker bonds, per trip excess liability and cargo, captive and self-insurance programs, owner-operator programs

2. Holmes Murphy, for Alternative Risk Financing

Holmes Murphy was founded in 1932 during the Great Depression and has grown into one of the largest independently owned brokers in the country, headquartered in Waukee, Iowa. Its transportation practice is staffed by a dedicated team with real-world fleet experience and builds programs covering auto liability, physical damage, cargo, and bobtail coverage. The firm’s captive capabilities are a standout, supported by its Innovative Captive Strategies subsidiary and its acquisition of Global Captive Management, giving qualified fleets a path into alternative risk financing.

Transportation is one practice among dozens at Holmes Murphy, which also serves construction, manufacturing, healthcare, and employee benefits clients, so commercial vehicle operators share firm resources with many other industries. Its captive and risk-financing strengths are geared toward larger, well-capitalized fleets, making it a less natural fit for small and mid-size operators. Self-service tools for after-hours certificates or short-term coverage are not a prominent part of its transportation offering, and its strong review average rests on a small number of public reviews spread across several offices.

Location: Waukee, IA (additional offices including South Dakota and Texas)

Founded: 1932

Avg. Review Score: 4.7/5.0

Price Range: $$$

Services: Auto liability, physical damage, motor truck cargo, bobtail and non-trucking liability, workers’ compensation, captive programs, risk assessment and loss control, employee benefits

3. Joe Morten & Son, for Established Multi-State Operations

Joe Morten & Son opened in South Sioux City, Nebraska in 1936. It has focused on commercial trucking insurance ever since. That makes it one of the oldest trucking agencies in the country. Its early growth was strong enough to help establish Great West Casualty Company in 1956. Great West went on to become one of the best-known trucking carriers in the United States. The agency now has ten offices and serves thousands of customers across 46 states. Many of its agents have worked with the same clients for decades as long-term advisors.

The agency’s digital service offering is fairly traditional, with most certificate, endorsement, and claim requests routed through agents rather than self-service tools available around the clock. Its identity is also closely tied to a single flagship carrier relationship, which works well for fleets that fit that carrier’s appetite but can narrow options for those that do not. As a legacy agency built on referrals, it has collected only a handful of public reviews, which makes it harder for new prospects to gauge the client experience before they call.

Location: South Sioux City, NE (10 locations nationwide)

Founded: 1936

Avg. Review Score: 3.8/5.0

Price Range: $$$$

Services: Commercial auto liability, physical damage, motor truck cargo, general liability, workers’ compensation, excess liability, occupational accident, owner-operator programs

4. Cottingham & Butler, for Large Fleets Seeking Captive Programs

Cottingham & Butler started in Dubuque, Iowa in 1887. It is now one of the largest privately held insurance brokers in the country. Its transportation division represents about 2,300 trucking clients. It is also the sole producer for the two largest transportation captives in the world. Those captives report a 99% member retention rate. Larger fleets get in-house claims and safety teams plus the proprietary IRIS client portal. Together, these create a structured, data-driven service model.

Transportation is one division inside a much broader firm that also serves employee benefits, agribusiness, manufacturing, and construction clients, so commercial vehicles are not the organization’s sole focus. Its service model is built around mid-size and large fleets, which can leave smaller operators working through layers of account staff rather than speaking directly with senior decision-makers. Premiums in the segment it serves tend to run higher per unit, and its public Birdeye rating is low, at 1.2 out of 5 across 34 reviews of its Dubuque listing.

Location: Dubuque, IA

Founded: 1887

Avg. Review Score: 1.2/5.0 (Birdeye, 34 reviews)

Price Range: $$$

Services: Auto liability, physical damage, motor truck cargo, workers’ compensation, group captives, large deductible programs, safety and claims management, employee benefits

5. Hylant, for Specialty Hauling Programs

Hylant was founded in Toledo, Ohio in 1935 by Edward P. Hylant and remains a family-owned brokerage, now with more than 1,000 professionals across roughly 20 offices. Its transportation and logistics team works exclusively within the industry, serving asset-based motor carriers, owner-operators, freight brokers, and warehouse operations. The firm has built specialty programs for niche segments, including its Car Haulers Insurance Program, and backs fleet clients with the Hylant Risk Management Center and fleet management resources.

Hylant’s footprint is concentrated in Ohio, Michigan, Indiana, and the Southeast, and while it has an office in Bloomington, Indiana, its transportation leadership is based in Toledo rather than the Upper Midwest. As a large multi-line broker, it delivers transportation services alongside employee benefits, personal lines, and general commercial accounts, so fleets work with one specialty group inside a much larger organization. Its client reviews are solid but uneven from office to office, ranging from 4.1 in Ann Arbor to 4.8 in Fort Wayne.

Location: Toledo, OH (offices across OH, MI, IN, IL, MN, and the Southeast)

Founded: 1935

Avg. Review Score: 4.3/5.0

Price Range: $$$

Services: Motor carrier auto liability, physical damage, motor truck cargo, general liability, freight brokerage coverage, car hauler programs, fleet risk management, employee benefits

6. Marvin Johnson & Associates, for Trucking-Built Claims Handling

Marvin Johnson spent a decade writing truck insurance from a friend’s truck terminal. In 1971, he opened his own agency in Columbus, Indiana. The second and third generations of the Johnson family now run the business. It has become one of the largest independent truck insurance agencies in Indiana, Ohio, and Illinois. The team includes roughly 70 insurance professionals. Claims handling is built for vehicles on the road. The focus is on reporting accidents right away, investigating on scene, and getting repairs done fast. Fleet clients can also use its safety services and mock DOT audits.

The agency’s footprint is concentrated in the Ohio Valley and Great Lakes region, so fleets based in Minnesota, the Dakotas, or western Wisconsin will find fewer local resources. It also writes personal, business, and employee benefits coverage, which means trucking is a core specialty rather than its only line. Self-service tools for after-hours coverage changes are limited, and its online review presence does not extend much beyond an A+ rating from the Better Business Bureau.

Location: Columbus, IN (additional office in Akron, OH)

Founded: 1971

Avg. Review Score: 4.2/5.0

Price Range: $$$$

Services: Auto liability, physical damage, motor truck cargo, workers’ compensation, safety services, mock DOT audits, driver risk management

7. TrueNorth Companies, for Data-Driven Fleet Risk Management

TrueNorth Companies is a closely held brokerage focused on risk management and insurance. It is based in Cedar Rapids, Iowa. About 550 colleagues work across its offices in Iowa, Illinois, and Colorado. In 2022, the American Trucking Associations gave its transportation practice a Mike Russell Trucking Image Award. The firm also appears among Insurance Journal’s Top 100 independent agencies. A January 2024 partnership with fleet risk platform Haul added driver and safety data tools. Those tools help fleets spot risk before it becomes a claim.

Transportation accounts for roughly 40% of TrueNorth’s revenue, with the remainder spread across construction, professional liability, employee benefits, and personal lines. That multi-practice structure and its size mean fleets typically work through a service team rather than directly with firm leadership. Founded in 2001, the firm is younger than several legacy agencies in this comparison, and its public review base is small, with a 4.1/5.0 Birdeye rating.

Location: Cedar Rapids, IA (additional offices in Illinois and Colorado)

Founded: 2001

Avg. Review Score: 4.1/5.0

Price Range: $$$

Services: Auto liability, physical damage, motor truck cargo, workers’ compensation, fleet risk management and safety consulting, employee benefits, driver programs

8. Lockton, for Enterprise-Scale Fleets

Lockton was founded in Kansas City, Missouri in 1966 and has grown into the largest privately held insurance broker in the world, with more than 150 offices. Its transportation team has served the industry for more than 30 years across truckload, less-than-truckload, dedicated, bulk and tank, carhaul, and final-mile segments. For large fleets, Lockton handles time-sensitive administrative work such as cab card issuance, insurance certificates, and federal and state filing management, and it designs fleet risk management structures aimed at lowering total cost of risk.

Lockton’s scale and global client base mean its transportation practice is geared toward enterprise fleets, and small and mid-size commercial vehicle operators may struggle to get the same level of attention. Fleets work through account teams within a very large organization rather than reaching senior leadership directly. Premiums in the segment it serves sit at the higher end of this comparison, and its strong public review score comes largely from its small-business digital agency, Mylo, rather than from transportation clients.

Location: Kansas City, MO (150+ offices worldwide)

Founded: 1966

Avg. Review Score: 4.8/5.0

Price Range: $$

Services: Auto liability, physical damage, motor truck cargo, workers’ compensation, fleet risk management, alternative risk structures, cab card and filing management, employee benefits

9. Aronson Group, for Fast Quotes on Small Fleets

Aronson Group launched in Bettendorf, Iowa in 2017. Its goal was to use technology to make trucking insurance easier for small fleets. The agency built its own platform to automate quote submission work and shorten quoting time. As a result, most clients get quotes within 24 hours. Aronson now serves more than 5,000 trucking businesses nationwide. It holds a 4.9/5.0 rating across 55 reviews.

Aronson works exclusively with fleets of one to nine units, so operators that grow past ten vehicles will eventually outgrow its model. Its product lineup centers on core lines rather than the broader program options larger fleets need, and its technology is focused on quoting speed more than ongoing policy self-service. As the youngest agency in this comparison, it also has the shortest track record through hard insurance markets.

Location: Bettendorf, IA

Founded: 2017

Avg. Review Score: 4.9/5.0

Price Range: $$

Services: Commercial auto liability, physical damage, motor truck cargo, new venture coverage, FMCSA filings, certificates of insurance

10. PJC Insurance Agency, for Regional Missouri and Plains Fleets

PJC Insurance Agency opened in Springfield, Missouri in 1968. Much of its early growth came from placing coverage for Midwestern truck fleets of one to 200 units. Today its transportation department places coverage in 17 states. It works with more than 100 A-rated carriers. The agency is a subsidiary of Sunstar Insurance Group. Sunstar is one of the larger independently owned brokers in the country.

Transportation is one department within a full-line agency that also writes personal insurance, employee benefits, and surety bonds, so commercial vehicles are not its exclusive focus. Its transportation footprint is limited to 17 states, which can be restrictive for fleets running national lanes, and it has little presence in the Upper Midwest. The agency also offers limited self-service tools for after-hours requests, and most of its public reviews come from personal lines customers rather than commercial fleets.

Location: Springfield, MO

Founded: 1968

Avg. Review Score: 4.8/5.0

Price Range: $$$$

Services: Commercial auto liability, physical damage, motor truck cargo, general liability, workers’ compensation, surety bonds, commercial property

Conclusion

The best commercial fleet insurance agency for a given operation depends on fleet size, where the vehicles run, how often coverage needs change, and how much direct support the owner expects. The agencies on this list cover that full range, from small fleets that want a fast quote to enterprise carriers building complex risk-financing structures.

Truck Writers ranked first because it removes the waiting from fleet insurance. Clients can handle certificates, claims, payments, and per trip excess coverage on their own schedule, reach the agency’s leadership directly when a decision needs to be made, and rely on a family-owned team rooted in the Upper Midwest that writes primary trucking coverage in 13 states and non-trucking and bobtail coverage across 38 states. More than four decades of trucking focus and independent access to multiple carriers keep that service backed by competitive pricing.

The Best Commercial Fleet Insurance Agencies by Specialty

Best for 24/7 Self-Service and After-Hours Coverage

1. Truck Writers
2. Aronson Group
3. Cottingham & Butler
4. TrueNorth Companies
5. Hylant

Best for Minnesota and Upper Midwest Commercial Vehicle Fleets

1. Truck Writers
2. Cottingham & Butler
3. Holmes Murphy
4. TrueNorth Companies
5. Joe Morten & Son

Best for Direct Access to Experienced Agents

1. Truck Writers
2. Joe Morten & Son
3. Marvin Johnson & Associates
4. Aronson Group
5. PJC Insurance Agency

Ready to compare commercial fleet insurance built around how your vehicles actually run? Contact Truck Writers for a Fleet Insurance Quote

Sources

1. Truck Writers: The Best Trucking Insurance Agency in the US, About Our Agency, Meet Our Team, Insurance Companies, Per Trip Excess Coverage, Captive and Self-Insurance Programs.
2. Google Business Profile: Truck Writers Inc., Blaine, MN, accessed October 2026.
3. Acuity: Truck Writers Celebrates 3 Generations of Family-Focused Success, At 50 Years, Marvin Johnson & Associates Keeps On Rolling.
4. Cottingham & Butler: About, Transportation Captives.
5. Wanderlog: Cottingham & Butler, Dubuque, IA (Google reviews).
6. Birdeye: Cottingham & Butler, Inc. Reviews, Joe Morten & Son Reviews, Holmes Murphy & Associates Reviews, Dallas, TX, Holmes Murphy & Associates Reviews, Davenport, IA, Holmes Murphy Reviews, Peoria, IL, Hylant Group Reviews, Ann Arbor, MI, Hylant Group Reviews, Fort Wayne, IN, TrueNorth Companies Reviews, West Des Moines, IA, Mylo, a Lockton Company Reviews, PJC Insurance Reviews.
7. Great West Casualty Company: About Great West.
8. Better Business Bureau: Joe Morten & Son Inc, Hylant Group, Inc., Marvin Johnson & Associates, Inc..
9. Holmes Murphy: Transportation, Our History.
10. Business Insurance: Holmes Murphy Buys Captive Manager.
11. Hylant: Transportation & Logistics, Car Haulers Insurance Program, Our History, Hylant Named a Best Place to Work in Insurance for 18th Consecutive Year.
12. Built In Chicago: Hylant.
13. Mployer Advisor: Hylant, Toledo, OH.
14. Marvin Johnson & Associates: Safety Services.
15. TrueNorth Companies: TrueNorth Wins Prestigious Trucking Industry Award.
16. FleetOwner: Haul Partners with TrueNorth Companies to Provide Final Mile Delivery Solutions.
17. Yahoo Local: TrueNorth Companies, Cedar Rapids, IA (Yelp reviews).
18. FreightWaves: Modernizing Insurance Will Keep Small Fleets’ Wheels Turning.
19. CB Insights: Aronson Group.
20. Lockton: Transportation.
21. Wikipedia: Lockton Companies.
22. PJC Insurance Agency: Personal & Business Insurance in Springfield, MO.