Best Commercial Fleet Insurance Agencies for Trucking: A Comprehensive Review in 2026

From July through September 2026, our research team evaluated independent agencies and brokers that place commercial fleet insurance for trucking companies, especially focusing on firms rooted in the Midwest and those serving Midwest carriers nationally. Below breaks down the full methodology, where each agency was scored using a seven-factor algorithm:

• Trucking-Exclusive Focus and Ownership Continuity (20%): Agencies that write only trucking under stable ownership carry institutional knowledge that survives staff turnover and carrier cycles.
• Fleet Program Depth (20%): Fleets need more than auto liability and cargo, so we weighted access to captives, self-insurance, freight broker bonds, excess coverage, and workers’ compensation.
• Dedicated Service and Compliance Support (20%): A named account team and in-house safety and CSA resources keep certificates moving and keep premiums from creeping upward.
• Year Founded (10%): Longevity in trucking 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 estimated the typical annual premium per power unit for each agency’s core fleet segment based on its carrier mix and client profile.
• 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 Trucking in 2026

1. Truck Writers, for Trucking-Only Fleet Programs and Compliance Support

Truck Writers has worked exclusively in trucking insurance since 1984, a year after Donald and Bonnie Sullivan opened the agency in 1983, right around the time the industry was deregulated. More than four decades later it is still family-owned and family-run, with their son Shawn Sullivan serving as CEO and Mackenzie Thompson as COO, and it has grown into one of the largest truck insurance agencies in the Midwest. Every fleet client is assigned a dedicated account team backed by a dedicated support team, and agents start each account with an analysis of the fleet’s operation so the program is built around actual risk rather than a generic template. As an independent agency, Truck Writers shops coverage across a carrier panel that includes Great West Casualty, National Indemnity, Northland, Progressive, Travelers, Canal, Great American, and Acuity.

Where Truck Writers separates itself is program depth paired with compliance support. The agency is a licensed third-party administrator for a transportation insurance captive and a self-insured workers’ compensation program, offers freight broker bonds, and runs a self-service per trip excess liability and cargo product available around the clock. Fleet clients also get access to CSA resources, safety documents, sample policies and procedures, and a training video library, along with a client portal for certificates and policy documents. The agency writes primary trucking coverage in 13 states (non-trucking and bobtail coverage in 38 states), with its deepest market presence across Minnesota, Wisconsin, Iowa, North Dakota, and South Dakota, which makes it a strong fit for Midwest-based fleets running regional and national lanes.

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: $8,500 to $14,000 per power unit annually (est.)

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. Cottingham & Butler, for Large-Fleet Captive Programs

Cottingham & Butler traces its roots to 1887 in Dubuque, Iowa, and has grown into one of the largest privately held insurance brokers in the country. Its transportation division represents about 2,300 trucking clients and works with every major commercial trucking carrier. The firm has offered group captives to transportation companies since 1993 and is the sole producer for the two largest transportation captives in the world, with more than 252 captive members and a reported 99% retention rate. In-house transportation claims and safety teams, plus the proprietary IRIS client portal, round out a program built for fleets that want to take control of their insurance spend.

Transportation is one division inside a much broader firm that also serves employee benefits, food and agribusiness, manufacturing, and construction clients, so trucking is not the organization’s sole focus. Its captive model is designed for mid-size and larger fleets with mature safety programs and the capital to participate, which means smaller carriers may find the processes better suited to operations bigger than theirs. Premiums in the segment it serves tend to run higher per unit, and its public Birdeye rating is low, at 1.2/5.0 across 34 reviews.

Location: Dubuque, IA

Founded: 1887

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

Price Range: $10,000 to $18,000+ per power unit annually (est.)

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

3. RJS Truck Insurance, for Responsive Multi-Carrier Account Service

RJS Truck Insurance has served the trucking industry since 1991, placing coverage for everyone from owner-operators to fleet accounts from its base in Laguna Niguel, California. The agency holds a 4.9/5.0 Google rating across more than 375 reviews, one of the strongest verified satisfaction scores in commercial trucking insurance. It shops a carrier roster that includes Great West Casualty, Progressive, Great American, Northland, and Wilshire, and clients repeatedly describe agents who stay personally reachable for years after the sale.

RJS operates from Southern California, so Midwest fleets will be working with an agency that does not have a physical presence in their region. Its product set centers on standard trucking lines, and it does not publicly offer captive or self-insurance programs for fleets looking to move beyond the traditional market. The agency’s strongest reputation is with owner-operators and new authorities, which makes it a less natural fit for larger fleets that need structured risk-financing options.

Location: Laguna Niguel, CA

Founded: 1991

Avg. Review Score: 4.9/5.0

Price Range: $9,000 to $16,000 per power unit annually (est.)

Services: Auto liability, physical damage, motor truck cargo, bobtail, non-trucking liability, occupational accident, general liability, workers’ compensation

4. Joe Morten & Son, for Established Multi-State Fleets

Joe Morten & Son has specialized in commercial trucking insurance since 1936, making it one of the oldest trucking agencies in the country. Founded in South Sioux City, Nebraska, the agency grew quickly enough to help establish Great West Casualty Company in 1956, which became one of the best-known trucking carriers in the United States. Today it serves thousands of customers across 46 states from ten office locations, with a product lineup that spans auto liability, cargo, workers’ compensation, excess liability, and owner-operator programs.

The agency’s identity is 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. It does not publicly promote captive or self-insurance programs for fleets ready to take on more of their own risk. As a legacy agency built on referrals, it has a limited public review presence, with a 3.8/5.0 Birdeye rating, 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: $9,000 to $15,000 per power unit annually (est.)

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

5. Marvin Johnson & Associates, for Trucking-Focused Claims Support

Marvin Johnson & Associates was founded in Columbus, Indiana in 1971 by Marvin Johnson, who spent a decade writing truck insurance from a friend’s truck terminal before opening his own agency. Now run by the second and third generations of the Johnson family, it has grown into the largest independent truck insurance agency in Indiana, Ohio, and Illinois, with an additional office in Akron, Ohio and roughly 70 insurance professionals. Its claims service is designed around trucking, with an emphasis on immediate accident reporting, on-scene investigations, and fast repairs, and the agency adds safety services and mock DOT audits for fleet clients.

The agency’s footprint is concentrated in the Ohio Valley and Great Lakes region, so fleets based further west may find fewer local resources. It also operates as a full-service agency writing personal, business, and employee benefits coverage, which means trucking is a core specialty rather than its only line. Captive and self-insurance options are not part of its public offering, and its online review presence is limited 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: $9,000 to $15,000 per power unit annually (est.)

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

6. TrueNorth Companies, for Risk Management Resources

TrueNorth Companies is a closely held risk management and insurance brokerage firm headquartered in Cedar Rapids, Iowa, with offices in Iowa, Illinois, and Colorado and approximately 550 colleagues nationwide. Its transportation practice earned a Mike Russell Trucking Image Award from the American Trucking Associations in 2022, recognizing its work with state trucking associations and industry nonprofits, and the firm ranks among Insurance Journal’s Top 100 independent agencies. A January 2024 partnership with fleet risk platform Haul added another layer of driver and safety data to its transportation offering.

Transportation accounts for roughly 40% of TrueNorth’s revenue, with the rest spread across construction, professional liability, employee benefits, and personal lines. That multi-practice structure, combined with its size, means fleets are working with one division of a large brokerage rather than a trucking-only shop. Founded in 2001, the firm is also younger than several legacy trucking agencies, and its public client reviews are limited, 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: $10,000 to $17,000 per power unit annually (est.)

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

7. Marquee Insurance Group, for Technology-Driven Quoting

Marquee Insurance Group was founded in 2014 by leaders from Nolan Transportation Group and OTR Solutions, giving it roots in freight brokerage and factoring rather than traditional insurance. Based in Roswell, Georgia, the agency accesses 30-plus A-rated markets and has been named DAT’s preferred liability insurance partner for motor carriers. Its Express Lane portal, BOOST safety monitoring program, premium financing, and fuel discount partnerships create a connected experience for carriers that want to manage their policies digitally.

With just over a decade in business, Marquee has a shorter track record than most agencies in this comparison. Its Southeast base and its strength with new authorities and smaller carriers make it less of a natural fit for established Midwest fleets with complex programs. A share of its online reviews also mention billing and renewal issues that required direct follow-up to resolve.

Location: Roswell, GA (additional offices in Georgia and Tennessee)

Founded: 2014

Avg. Review Score: 4.3/5.0

Price Range: $9,500 to $18,000 per power unit annually (est.)

Services: Auto liability, physical damage, motor truck cargo, general liability, workers’ compensation, freight broker insurance, BOOST safety monitoring, premium financing

8. Reliance Partners, for Cross-Border and Alternative Risk Programs

Reliance Partners was founded in Chattanooga, Tennessee in 2009 and has become one of the fastest-growing trucking and logistics insurance agencies in the country, serving more than 8,000 trucking companies and freight brokers. The firm offers captive and self-insurance programs, usage-based insurance, and specialty cross-border programs for carriers running into Canada and Mexico. It has appeared on the Inc. 5000 list for seven consecutive years (as of 2022), been named one of Fortune’s Best Workplaces in Financial Services and Insurance, and was recognized by Women In Trucking as a Top Company for Women to Work in Transportation in 2024.

Reliance’s rapid growth has come with mixed client feedback, and its Trustpilot rating sits at 2.3/5.0 across a small sample, with several reviewers citing follow-up and service issues. The firm also writes hospitality and manufacturing accounts, so trucking is its core rather than its only focus. Its Southeast headquarters means Midwest fleets will be served primarily by a national team rather than a local office.

Location: Chattanooga, TN

Founded: 2009

Avg. Review Score: 2.3/5.0

Price Range: $9,500 to $17,000 per power unit annually (est.)

Services: Auto liability, physical damage, motor truck cargo, freight broker insurance, captive and self-insurance programs, usage-based insurance, cross-border coverage, safety consulting

9. Aronson Group, for Small Fleets and New Ventures

Aronson Group was founded in Bettendorf, Iowa in 2017 with a clear mission: use technology to take friction out of trucking insurance for small fleets. The agency built a proprietary platform that automates quote submission workflows and compresses quoting timelines, so most clients receive quotes within 24 hours. It has grown to serve more than 5,000 trucking businesses nationwide and holds a 4.9/5.0 rating across 55 reviews.

Aronson works exclusively with fleets of one to nine units, so carriers that grow past ten trucks will eventually outgrow its model. It does not offer captive or self-insurance programs, and its product lineup centers on core lines rather than the broader program options larger fleets need. 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: $10,000 to $18,000 per power unit annually (est.)

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

10. PJC Insurance Agency, for Regional Midwest Fleets

PJC Insurance Agency was founded in Springfield, Missouri in 1968 and built much of its early growth placing coverage for Midwestern truck fleets ranging from one to 200 units. Its transportation department now places coverage in 17 states and places business through more than 100 A-rated carriers. As a subsidiary of Sunstar Insurance Group, the agency also has the backing of 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 trucking is not its exclusive focus. Its transportation footprint is limited to 17 states, which can be restrictive for fleets running national lanes. The agency also does not publicly offer captive or self-insurance programs, and it lacks an aggregated public review score for its commercial clients.

Location: Springfield, MO

Founded: 1968

Avg. Review Score: 4.8/5.0

Price Range: $8,500 to $14,500 per power unit annually (est.)

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, hauling territory, safety maturity, and how much hands-on account support you need. The agencies on this list represent the strongest options across that full range, from small fleets that want a fast, straightforward quote to large carriers ready to move into a group captive.

Truck Writers ranked first because of what it combines: more than four decades of exclusive trucking focus, three generations of family ownership, a dedicated account team for every fleet, true multi-carrier independence that keeps pricing competitive, and program depth that includes captive and self-insurance administration, freight broker bonds, and per trip excess coverage. Every recommendation is built around the specific demands of running trucks, not adapted from a general commercial lines playbook.

The Best Commercial Fleet Insurance Agencies by Specialty

Best for Small and Mid-Size Fleets (5 to 50 Trucks)

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

Best for Dedicated Account Service and Compliance Support

1. Truck Writers
2. RJS Truck Insurance
3. Cottingham & Butler
4. Marvin Johnson & Associates
5. TrueNorth Companies

Best for Upper Midwest Fleets (MN, WI, IA, ND, SD)

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

Ready to compare fleet insurance options built for trucking? Request a Fleet Insurance Quote from Truck Writers

Sources

1. Truck Writers: The Best Trucking Insurance Agency in the US.
2. Acuity: Truck Writers Celebrates 3 Generations of Family-Focused Success.
3. Facebook: Truck Writers.
4. Google Business Profile: Truck Writers Inc., Blaine, MN, accessed October 2026.
5. MENAFN: Highway Launches Highway Certified Insurance Agencies, A New Standard for Trust in Brokered Freight.
6. Cottingham & Butler: Trucking Captives.
7. Verizon Connect: Cottingham & Butler.
8. Better Business Bureau: Marvin Johnson & Associates, Inc..
9. Intermodal Association of North America: UIIA Insurance Agent Directory.
10. Insurance Xdate: Joe Morten & Son, Inc..
11. Built In: Great West Casualty Company.
12. LinkedIn: Marvin Johnson & Associates.
13. TCA Supplier Directory: Marvin Johnson & Associates.
14. Marvin Johnson & Associates: Complete Annual Review.
15. TrueNorth Companies: TrueNorth Wins Prestigious Trucking Industry Award.
16. Craft: TrueNorth Company Profile.
17. DAT: Affordable Commercial Truck Insurance.
18. Simplify: Marquee Insurance Group.
19. FreightWaves: Marquee Takes Educational Approach to Insurance, Unveils Tech.
20. Reliance Partners: Reliance Partners Earns Inc. 5000 Listing for 7th Straight Year.
21. Trustpilot: Reliance Partners Reviews.
22. Birdeye: Cottingham & Butler, Inc. Reviews, Joe Morten & Son Reviews, TrueNorth Companies Reviews, West Des Moines, IA.
23. CB Insights: Aronson Group.
24. Mediabistro: Aronson Group LLC, Account Manager.
25. 417 Magazine: PJC Insurance Agency, The Face of Independent Insurance.
26. Springfield Business Journal: Small Business Finalists: PJC Insurance.
27. PJC Insurance Group: Personal and Business Insurance in Springfield, MO.