The Best Fleet Insurance Agencies of 2026
From March through May 2026, our research team evaluated 40+ fleet insurance agencies serving commercial trucking operations across the United States. We focused exclusively on independent agencies. These businesses represent multiple carriers and act as an intermediary between fleet operators and the insurers that underwrite coverage. We pulled data from agency websites, carrier filings, industry publications, and direct outreach to agency representatives. Each agency was scored using a six-factor algorithm:
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Years in Business (20%): Length of time the agency has operated as a licensed independent broker serving commercial fleet accounts. Fleet insurance is a B2B product where public client reviews are rarely collected, so agency longevity serves as the primary trust signal.
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Fleet Coverage Options (20%): Breadth and depth of products built specifically for multi-truck operations, including specialty endorsements and captive or alternative risk programs.
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Safety & Risk Management Resources (20%): Availability of loss prevention programs, CSA score support, driver safety tools, telematics integrations, and risk consulting services.
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Account Service Quality (15%): Responsiveness of the dedicated account team, certificate of insurance (COI) turnaround speed, and quality of day-to-day support for fleet clients.
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Carrier Access (15%): Number and quality of insurance carriers the agency can access on behalf of fleet clients.
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Trucking Specialization (10%): Percentage of the agency’s total book of business focused exclusively on commercial trucking and transportation insurance.
We rank-ordered every agency in our dataset using this algorithm. The table below presents the top six performers, followed by in-depth reviews of each.
The Best Fleet Insurance Agencies of 2026
1. Truck Writers, for Dedicated Multi-Carrier Fleet Coverage
Founded in Blaine, Minnesota in 1983, Truck Writers is a family-owned independent insurance agency with over four decades of experience in commercial trucking insurance. The agency is the only one on this list that works exclusively in trucking. Every agent, account manager, and support staff member focuses solely on commercial trucking operations. That specialization translates directly into faster, more accurate quoting, fewer coverage gaps, and account teams that understand the day-to-day demands of running a fleet.
Fleet operators receive a dedicated account team assigned to their account from day one, with same-day COI turnaround and a quote window of 24 to 48 hours. Because Truck Writers represents multiple insurance carriers rather than a single market, fleet owners receive competing rates across carriers rather than a single take-it-or-leave-it price. Coverage includes auto liability, physical damage, motor truck cargo, workers’ compensation, freight broker insurance, per trip excess coverage, and captive or self-insurance programs for qualifying fleets. The agency holds licenses in 38 states and has built its 43-year reputation entirely within commercial trucking, with no general commercial lines business competing for staff time or resources.
Location: Blaine, MN (additional office in Welcome, MN)
Year Founded: 1983
Services Offered: Auto liability, physical damage, motor truck cargo, workers’ compensation, freight broker insurance, per trip excess, captive and self-insurance programs
Fleet Sizes Served: Owner operators through large motor carriers
Summary of Online Reviews: Clients frequently highlight responsive account teams, competitive rates from multiple carriers, and fast COI turnaround. Fleet clients note that having a dedicated agent who understands trucking specifically is the most cited reason they stay at renewal.
2. Higginbotham, for All-Size Fleet Programs and Risk Management Depth
Higginbotham was founded in Fort Worth, Texas in 1948 and has grown into one of the largest employee-owned insurance brokerages in the United States. Its transportation and fleet practice serves motor carriers of every size, from small fleets of two to ten power units all the way to national fleets operating more than 500 units. The agency’s transportation team brings more than 300 combined years of fleet insurance and risk management experience, and the firm invests ten times the national average in staff education and training to maintain that depth of expertise.
Fleet clients benefit from a full range of coverage including motor carrier liability, physical damage, motor truck cargo, workers’ compensation, occupational accident, commercial general liability, umbrella and excess liability, non-trucking use liability, and independent contractor programs. Higginbotham administers IC programs using proprietary software that typically reduces administrative costs by 30 to 40 percent compared to competing agencies. This is a meaningful advantage for motor carriers running large independent contractor programs. Captive and self-insurance programs are available for established fleets seeking alternative risk financing. Safety and loss prevention services round out the offering, giving fleet operators tools to manage CSA scores and reduce long-term claim frequency.
Location: Fort Worth, TX (multiple offices)
Year Founded: 1948
Services Offered: Motor carrier liability, physical damage, motor truck cargo, workers’ comp, occupational accident, CGL, umbrella and excess, non-trucking liability, IC programs, captive and self-insurance
Fleet Sizes Served: Small (2-10 units), Large (10-500 units), National (500+ units)
Summary of Online Reviews: Higginbotham does not maintain a widely aggregated public review presence, which is common among B2B fleet insurance brokers. The agency’s 78-year track record and employee-owned structure reflect a client retention model built on long-term relationships rather than online marketing.
3. Lockton Transportation, for Large and Complex Fleet Risks
Lockton was founded in Kansas City, Missouri in 1966 and has grown into the world’s largest privately held insurance broker. Its Transportation and Logistics practice has focused on commercial fleet risks for more than 30 years, with a team of 30+ dedicated transportation specialists who place and service large, complex trucking accounts that most regional agencies are not equipped to handle. Coverage spans auto liability, cargo, physical damage, workers’ compensation, general liability, occupational accident, non-trucking liability, umbrella and excess liability, errors and omissions, broker liability, property, shipper’s interest, stock throughput, and warehouse legal.
Lockton’s industry reach extends across every major trucking segment: LTL, truckload, dry van, drayage, refrigerated, flatbed, tanker, bulk, car hauler, moving and storage, and driveaway operations. The firm maintains access to specialty wholesale markets and reinsurers that are out of reach for most agencies, giving large motor carriers pricing options that smaller brokers simply cannot access. Lockton is also actively involved in transportation industry advocacy at the national, state, and local level. This advocacy is an asset for fleets navigating regulatory changes, nuclear verdict trends, and insurance market hardening. The primary limitation is that Lockton focuses on large and complex accounts; smaller fleets may find better-suited partners among the agencies lower on this list.
Location: Kansas City, MO (US headquarters)
Year Founded: 1966 (Transportation practice: 30+ years)
Services Offered: Auto liability, cargo, physical damage, workers’ comp, GL, occupational accident, NTL, umbrella and excess, E&O, broker liability, property, shipper’s interest, stock throughput, warehouse legal
Fleet Sizes Served: Mid-size through large and complex motor carriers
Summary of Online Reviews: Lockton does not have a meaningful public client review aggregate for its transportation practice. As the world’s largest privately held broker, its reputation is built on institutional relationships with large motor carriers and its standing in the commercial insurance industry rather than consumer review platforms.
4. Cottingham & Butler, for Fleet Captive Programs and Risk Consulting
Cottingham & Butler is one of the largest independent insurance brokers in the United States, with a transportation practice that has specialized in commercial fleet accounts for more than 30 years. Transportation accounts for approximately 60 percent of their commercial lines book, giving the transportation team a level of industry focus that most general brokerages do not match. The agency’s strength is its depth of risk consulting capability. Fleet operators receive not just insurance placement but a strategic advisory relationship built around reducing total cost of risk over time.
Coverage lines include auto liability, physical damage, motor truck cargo, general liability, workers’ compensation, and a well-regarded captive insurance program for mid-size to large motor carriers. The captive program allows qualifying fleets to retain more underwriting profit in years with favorable loss experience, rather than paying premiums to a commercial carrier. Loss control consulting and claims management services provide ongoing support between renewals. For fleets that have outgrown standard guaranteed-cost programs and are ready to explore alternative risk structures, Cottingham & Butler is one of the most experienced options in the country.
Location: Dubuque, IA
Year Founded: 30+ years in transportation insurance
Services Offered: Auto liability, physical damage, motor truck cargo, workers’ comp, GL, captive insurance programs, loss control consulting, risk management consulting
Fleet Sizes Served: Small fleets through large motor carriers; captive programs for mid-size and large fleets
Summary of Online Reviews: Clients frequently cite deep industry knowledge, strong captive program options, and a consultative approach that goes beyond standard policy placement. Some reviewers note that the agency’s processes are best suited to mid-size and larger fleet operations.
5. World Insurance Associates, for Growing Fleets Seeking Multi-Market Access
World Insurance Associates was founded in 2011 in Iselin, New Jersey and has grown into a Top 50 US brokerage through more than 200 acquisitions, several of which were specifically targeted at building out its commercial trucking book. Acquired agencies include Royalty Insurance Services, Future Insurance Group, and United American Insurance, each of which brought dedicated trucking teams, carrier relationships, and existing fleet accounts into the World platform. The result is a trucking practice staffed by transportation advisors with direct industry backgrounds, including agents who have worked as truckers themselves.
Coverage is available for all fleet sizes including long-haul, regional, fleet, non-fleet, and owner operator accounts. The agency’s multi-market access, built through over a decade of targeted acquisitions, allows fleet clients to compare rates across carriers rather than relying on a single market. Quote turnaround and account service quality vary by region and assigned team, which is a known limitation of acquisition-driven growth models. Fleet operators should confirm staffing continuity and dedicated account assignment when evaluating World Insurance Associates for their program.
Location: Iselin, NJ (multiple offices nationwide)
Year Founded: 2011
Services Offered: Commercial auto liability, physical damage, motor truck cargo, general liability, workers’ comp, fleet and non-fleet programs
Fleet Sizes Served: Small fleets through large motor carriers; fleet and non-fleet accounts
Summary of Online Reviews: World Insurance Associates has a limited public review presence across major platforms. Client feedback from its acquired trucking agency teams reflects satisfaction with market access and agent responsiveness, though service consistency can vary by regional office given the agency’s acquisition-driven growth model.
6. Acrisure Transportation, for Fleet Risk and Business Advisory Services
Acrisure was founded in 2005 and has grown into one of the largest independent insurance brokerages in North America through an aggressive acquisition strategy. Its transportation division serves commercial trucking companies with a model that extends beyond insurance placement into fleet risk consulting, employee benefits, and business advisory services. The agency’s stated mission for trucking clients is to help them reduce risk across their business by reducing exposure across insurance, driver safety, compliance, and operational risk rather than simply placing coverage at renewal.
Coverage includes commercial auto liability, physical damage, motor truck cargo, general liability, workers’ compensation, and occupational accident insurance. The transportation division also provides employee benefits programs and cybersecurity consulting for fleets that are modernizing their technology infrastructure. Service quality and dedicated account team access vary by regional office, which is typical for large national brokerages that have grown primarily through acquisition. Fleet operators with straightforward coverage needs may find that a more specialized trucking agency delivers faster service; those seeking a broader advisory relationship that covers insurance alongside HR and business strategy will find Acrisure’s model a strong fit.
Location: Grand Rapids, MI (US headquarters; offices nationwide)
Year Founded: 2005
Services Offered: Commercial auto liability, physical damage, motor truck cargo, GL, workers’ comp, occupational accident, employee benefits, cybersecurity consulting
Fleet Sizes Served: Small fleets through large motor carriers
Summary of Online Reviews: Acrisure does not maintain a widely aggregated public review score for its transportation division. The agency has grown primarily through acquisitions, and client experience varies by regional team. Fleet operators are encouraged to request references from the specific office and account team that would be assigned to their account.
The Best Fleet Insurance Agencies in the US by Specialty
We also broke down the top fleet insurance agencies into three subcategories based on fleet size and program type.
The Best Fleet Insurance Agencies for Small Fleets (2-9 Trucks)
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Truck Writers
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Higginbotham
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Cottingham & Butler
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World Insurance Associates
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Acrisure Transportation
The Best Fleet Insurance Agencies for Large Motor Carriers (10+ Trucks)
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Truck Writers
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Lockton Transportation
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Higginbotham
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Cottingham & Butler
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Acrisure Transportation
The Best Fleet Insurance Agencies for Independent Contractor Programs
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Truck Writers
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Higginbotham
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Cottingham & Butler
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Lockton Transportation
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World Insurance Associates
Conclusion
The best fleet insurance agency for a given operation depends on fleet size, cargo type, hauling territory, and the level of risk management support required. The agencies on this list represent the strongest independent options across that full range, from small fleets looking for straightforward multi-carrier coverage to large motor carriers seeking captive programs and complex risk consulting.
Truck Writers ranked first because of what it combines: 43 years of exclusive trucking focus, a dedicated account team for every fleet client, true multi-carrier independence that keeps pricing competitive, and a product depth that covers every stage of a fleet’s growth. It is the only agency on this list that works exclusively in commercial trucking. Every carrier relationship, every coverage recommendation, and every account service decision is built around the specific demands of the trucking industry.
