Alexander & Alexander

What Alexander & Alexander does

Alexander & Alexander Insurance Wholesalers, Inc. (operating as Alexander & Alexander Transportation Insurance, or A&A) is a privately held, Kentucky-based commercial trucking insurance brokerage founded in 1999. The firm acts as an intermediary, shopping coverage across multiple leading transportation insurance carriers to secure pricing for clients, and earns commissions on placed policies. A&A services owner operators, leased operators, and small fleet owners across 20+ US states through a dual-office presence in Leitchfield (headquarters) and Louisville (sales), with a 11-50 employee base. The company claims more than 60 years of specialized transportation insurance experience.

The core product portfolio consists of nine commercial trucking coverage lines: Primary Liability, Physical Damage, Motor Truck Cargo, General Liability, Excess/Umbrella, Workers Compensation, Non-Trucking Liability, Passenger Accident, and Occupational Accident insurance. All coverages are quote-based, priced per truck and tailored to fleet characteristics, with monthly billing. Underlying technology is built on third-party platforms: Vertafore powers the client policy portal and Xpress-Pay handles online premium payments. No proprietary underwriting models or AI/ML capabilities are disclosed.

A&A's go-to-market is sales-led and relationship-driven, combining a toll-free phone sales channel, online quote requests, and a referral pipeline through its sister organization, the American Association of Owner Operators (AAOO). Every A&A insured is automatically enrolled as an AAOO member, receiving free or discounted benefits — a structural retention mechanism that adds ecosystem value beyond the insurance policy itself. Pricing is not publicly disclosed; the firm cites average new-client savings of over $3,000 per truck as its primary value proposition against generalist competitors.

Name

Alexander & Alexander

Legal name

Alexander & Alexander Insurance Wholesalers, Inc.

Website

https://aatruckinsurance.com

Company type

Private

Founded year

1999

Operating status

Operating

Headcount range

11–50 employees

Short description

Alexander & Alexander is a privately held Kentucky-based insurance brokerage that places commercial trucking coverage across nine product lines for owner operators, leased operators, and small fleet owners in 20+ US states, earning carrier commissions on policies sourced through its sister organization, AAOO.

Ownership category

akta.pro rank

Product category

Commercial Trucking Insurance

NAICS

Insurance Agencies and Brokerages (524210), Agencies, Brokerages, and Other Insurance Related Activities (5242)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Wholesale Insurance Brokerage (Excess & Surplus Lines) (FSAEADAD)

akta.pro secondary industries

Motor Truck Cargo (FSAJABAC), Umbrella Insurance (FSAJAMAK)

Keywords

• Commercial trucking insurance
• Owner operator insurance
• Motor carrier coverage
• Transportation insurance agency
• Small fleet insurance

Headquarters

HQ city

Leitchfield

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Others

Revenue model

1. Insurance Agency/Brokerage Commissions: A&A acts as an insurance agency/brokerage, earning commissions from insurance carriers for placing trucking insurance policies. They shop coverage across multiple carriers to find the best pricing for clients.

Pricing tiers

Go-to-market motion1 record

Distribution channels1 record

Marketing channels3 records

Core offering

Alexander & Alexander is a full-service transportation insurance brokerage that places commercial trucking coverage with multiple leading insurance carriers for owner operators, leased operators, and small fleet owners. The agency offers nine distinct coverage lines — Primary Liability, Physical Damage, Motor Truck Cargo, General Liability, Excess/Umbrella, Workers Compensation, Non-Trucking Liability, Passenger Accident, and Occupational Accident — and operates across more than 20 states from offices in Leitchfield and Louisville, Kentucky.

Product overview

Alexander & Alexander (A&A) is a full-service transportation insurance agency offering a unified portfolio of commercial trucking insurance products. The core offering consists of nine distinct coverage types: Primary Liability, Physical Damage, Motor Truck Cargo, General Liability, Excess/Umbrella Coverages, Workers Compensation, Non-Trucking Liability, Passenger Accident, and Occupational Accident insurance. All coverages are sourced from multiple leading insurance carriers and tailored to each client's needs. As a value-added service, every A&A insured automatically receives a membership in the American Association of Owner Operators (AAOO), providing additional benefits and resources for owner operators and small fleet owners. The agency operates through a network of relationships with insurance carriers specializing in transportation coverage across over 20 states, with offices in Kentucky (Leitchfield and Louisville).

Differentiator

Problem solved

Functional benefit

Products and services

• Primary Liability Insurance Federal-mandated liability insurance that protects trucking businesses when a third party is injured in an accident. Required for every rig including leased units.
• Physical Damage Insurance
• Motor Truck Cargo Insurance
• General Liability Insurance
• Excess/Umbrella Coverages
• Workers Compensation
• Non-Trucking Liability Insurance
• Passenger Accident Coverage
• Occupational Accident Insurance
• AAOO Membership Benefits

Quantifiable outcome

• Average savings of over $3,000 per truck for new clients

Named customers3 records

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration3 records

Partnerships

One partnership is on record.

• American Association of Owner Operators (AAOO)coreStrategic or Co-development PartnerAAOO is a nationwide association for professional owner operators, leased operators, and small fleet owners. A&A automatically enrolls every insured as an AAOO member at the start of their policy, providing members with access to free or heavily discounted benefits. This partnership drives customer acquisition and retention by adding value beyond traditional insurance. Owner operators with AAOO are described as more likely to stay in business, make more money, and increase fleet size.

Scale indicators3 records

Expansion highlights4 records

Direct peers

• Reliance Partners: Reliance Partners is a national commercial trucking insurance brokerage specializing in owner-operator and fleet coverage. It is one of the closest direct competitors to A&A, offering multi-carrier placement across the same core trucking lines including Primary Liability, Physical Damage, Motor Truck Cargo, and Workers Comp.
• Owner Operators Insurance: Owner Operators Insurance is a niche commercial trucking insurance agency focused exclusively on owner-operators and small fleets. It competes head-to-head with A&A in the same customer segments and product set, including non-trucking liability and occupational accident coverages.
• SmartHaul Insurance Services: SmartHaul is a transportation-focused insurance agency serving owner-operators and small fleets with a multi-carrier placement model. It is directly comparable to A&A in target customer, product mix (Primary Liability, Cargo, Physical Damage), and brokerage distribution approach.
• Simplex Group: Simplex Group is a specialty insurance brokerage focused on commercial trucking and transportation risks. It serves the same owner-operator and small fleet SMB customer base as A&A and sources coverage from multiple transportation-specialist carriers.
• Bigg Insurance Group: Bigg Insurance Group is a transportation-focused insurance broker placing commercial trucking coverage with multiple carriers. It is comparable to A&A in its SMB owner-operator focus and emphasis on niche trucking products such as motor truck cargo and occupational accident.

Broad incumbents

• Progressive Commercial: Progressive Commercial is one of the largest direct writers of commercial trucking insurance in the U.S., including Primary Liability, Physical Damage, and Motor Truck Cargo. It competes with A&A for owner-operator and small fleet business, but at vastly greater scale and via direct/agent channels rather than a specialist brokerage model.
• Lockton: Lockton is the world's largest independent insurance brokerage, with commercial transportation and trucking practices. It is comparable to A&A as a commercial trucking insurance broker but serves substantially larger fleet accounts and operates at a national/global scale.

Emerging players

• NEXT Insurance: NEXT Insurance is a digital-first commercial insurance carrier serving small businesses including commercial trucking. It targets the same SMB trucking segment as A&A but competes via a fully online bind-and-issue model rather than a phone/sales-led brokerage approach.
• CoverWallet (Aon): CoverWallet is a digital commercial insurance platform that helps small businesses compare and buy coverage online, including commercial auto and trucking. It overlaps with A&A's SMB customer base but competes via an online experience rather than carrier-specialist brokerage service.
• Hwy Haul: Hwy Haul is a digital freight platform that also facilitates trucking insurance placement for owner-operators and small fleets. It addresses the same SMB trucking insurance pain points as A&A but via a technology-first model embedded in freight booking workflows.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks5 records

Key highlights5 records

Customer concentration

• LinkedInlinkedin.com/company/alexander-alexander-transportation-insurance
• Xx.com/aatruckins

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Alexander & Alexander