LR WINDSOR

What LR WINDSOR does

LR WINDSOR is an independent insurance agency founded in 2003 by Todd Johnson, headquartered in Chicago, Illinois, with a secondary office in Waukegan. The agency provides personal lines (auto, homeowners, condo, renters, motorcycle, boat, flood, rental property, high net worth, and personal umbrella), commercial lines (general liability, commercial property, workers' compensation, commercial auto, cyber, professional liability/E&O, D&O, EPLI, business interruption, surety bonds, and contractor's GL), and life/health and group benefits products (individual and group life, health, disability, dental, vision, long-term care, final expense, FSAs, HSAs, and worksite benefits). The agency represents 25+ national and regional insurance carriers including Erie Insurance, Chubb, Liberty Mutual, MetLife, Progressive, Prudential, Travelers, The Hartford, Aetna, Blue Cross Blue Shield, and UnitedHealthcare, earning commission revenue on policies placed through its carrier relationships. Adjacent financial and retirement planning services are offered through a subsidiary, LRW Financial.

The agency operates a sales-led, consultative distribution model combining local agents at physical offices with online instant quote tools and quote request forms on its website. It targets three primary customer segments: individuals and families seeking personal insurance, small to medium businesses needing commercial coverage, and employer groups requiring employee benefits. Geographic focus is concentrated in the Chicago metropolitan area and across Illinois, serving 15+ suburban markets including Evanston, Glenview, Lake Zurich, Oak Park, Oak Lawn, Orland Park, Schaumburg, and Gurnee. The technology infrastructure is conventional for an independent agency — a website-based consumer quote comparison tool, secure email encryption for client communications, and industry-standard agency management software (CSR24) — with no disclosed AI/ML capabilities, proprietary models, or differentiated platform technology.

Revenue is generated exclusively through affiliate/referral commissions from carrier partners on policies sold; pricing to end customers is structured as free comparative quotes across multiple carriers, with no disclosed fees or premium markups to the agency itself. The company is privately held with no parent company, no institutional investment disclosed, no funding rounds, and no acquisition history. Between 11 and 50 employees operate across two offices, and the business has grown organically over 23 years through carrier partnership expansion, product line extension into modern specialty coverages, and the addition of the LRW Financial subsidiary.

Name

LR WINDSOR

Legal name

LR WINDSOR

Website

https://lrwindsor.com

Company type

Private

Founded year

2003

Operating status

Operating

Headcount range

11–50 employees

Short description

LR WINDSOR is an independent insurance agency founded in 2003 that distributes personal, commercial, and group benefits insurance from 25+ carriers to individuals, families, and businesses across the Chicago metropolitan area and Illinois, operating from offices in Chicago and Waukegan.

Ownership category

akta.pro rank

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

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

Revenue model

1. Insurance Commission Revenue: LR WINDSOR earns commissions from insurance carriers for policies sold. As an independent agency, they represent multiple insurance companies and receive compensation when customers purchase policies through their agency.

Pricing tiers

Go-to-market motion1 record

Distribution channels2 records

Marketing channels5 records

Core offering

LR WINDSOR is an independent insurance agency that represents 25+ national and regional insurance carriers, providing comparative quotes and customized coverage solutions. The agency offers personal insurance (auto, home, boat, motorcycle, renters, condo, flood, umbrella), business insurance (general liability, commercial property, workers' compensation, cyber, professional liability, D&O, EPLI), and life/health insurance (individual and group health, life, disability, dental, vision, long-term care) to individuals, families, and businesses primarily in the Chicago metropolitan area and Illinois.

Product overview

LR WINDSOR is an independent insurance agency offering a comprehensive portfolio of insurance products and financial services. The company provides personal insurance (auto, homeowners, boat, motorcycle, renters, condo, flood, and umbrella coverage), business insurance (general liability, commercial property, workers' compensation, cyber, professional liability, D&O, and EPLI), and life/health insurance (individual and group health, life, disability, dental, vision, and long-term care). They also offer group benefits including FSAs, HSAs, and 401(k) retirement plans through their subsidiary LRW Financial. As an independent agency representing multiple carriers, they provide comparative quotes and customized coverage solutions for individuals, families, and businesses across Illinois.

Differentiator

Problem solved

Functional benefit

Products and services

• Auto Insurance Vehicle insurance covering liability, collision, comprehensive, and uninsured/underinsured motorist protection for personal vehicles, offered to individuals and families.
• Homeowners Insurance Property insurance protecting homeowners against damage, theft, and liability, including coverage for other structures and personal possessions.
• Business Insurance Comprehensive commercial coverage including property, liability, workers' compensation, and specialized business policies for various industries, serving business owners.
• Life, Disability, Long Term Care & Health Care Insurance Individual health and life insurance products including term life, universal life, whole life, disability, long-term care, and health insurance policies.
• Group Benefits Employer-sponsored benefit programs including group health, life, disability, dental, vision, long-term care insurance, and tax-advantaged accounts like FSAs and HSAs.
• Boat & Marine Insurance
• Motorcycle Insurance Coverage for motorcycles including collision, comprehensive, custom parts, and uninsured/underinsured motorist protection.
• Cyber Insurance Business coverage for data breaches, ransomware attacks, and cyber incidents including notification costs, legal fees, and recovery expenses.
• Professional Liability (Errors & Omissions) Insurance Protection against claims of misrepresentation, negligence, and errors or failure to render services, covering court costs and settlements.
• Workers' Compensation Insurance State-mandated coverage providing medical treatment and wage replacement for work-related injuries or illnesses.
• High Net Worth Coverage Concierge-level insurance for affluent clients covering primary/secondary residences, private collections, identity theft, and kidnap/ransom.
• Worksite Benefits Voluntary employee benefit programs offered at worksites including life, disability, accident, and critical illness insurance.

Quantifiable outcome

• Free comparative quotes from multiple carriers
• +1 more outcomes

Named customers2 records

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature2 records

Partnerships

18 partnerships are on record, tiered core, flagship and minor.

• AAA InsurancecoreChannel Partner/ Reseller/ DistributorNational insurance carrier offering auto, home, and other personal insurance products. LR WINDSOR represents AAA Insurance as an independent agent.
• AetnacoreChannel Partner/ Reseller/ DistributorHealth insurance provider offering individual and group health coverage. LR WINDSOR offers Aetna products to clients seeking health insurance.
• Blue Cross Blue ShieldcoreChannel Partner/ Reseller/ DistributorMajor health insurance provider offering comprehensive health coverage options. LR WINDSOR represents Blue Cross Blue Shield for health insurance needs.
• CNAcoreChannel Partner/ Reseller/ DistributorCommercial insurance carrier specializing in business insurance products. LR WINDSOR offers CNA products for business clients.
• Chubb GroupcoreChannel Partner/ Reseller/ DistributorPremium insurance carrier offering high-value personal and commercial coverage. LR WINDSOR represents Chubb for high net worth client coverage.
• Erie InsuranceflagshipChannel Partner/ Reseller/ DistributorRegional insurance carrier specializing since 1925 in auto, home, business, and life insurance. LR WINDSOR is a specialized Erie Insurance agency with dedicated auto, life, and bill payment links.
• The Hartford Insurance GroupcoreChannel Partner/ Reseller/ DistributorNational insurance carrier offering business and personal insurance products. LR WINDSOR offers Hartford products to clients.
• Liberty Mutual InsurancecoreChannel Partner/ Reseller/ DistributorNational insurance carrier offering auto, home, and business coverage. LR WINDSOR represents Liberty Mutual for various insurance needs.
• Metropolitan Life Insurance CompanycoreChannel Partner/ Reseller/ DistributorLife insurance and employee benefits provider. LR WINDSOR offers MetLife products for life and employee benefits.
• The Progressive CorporationcoreChannel Partner/ Reseller/ DistributorAuto insurance carrier known for competitive rates. LR WINDSOR offers Progressive auto insurance products.
• PrudentialcoreChannel Partner/ Reseller/ DistributorFinancial services company offering life insurance and retirement products. LR WINDSOR represents Prudential for life insurance.
• The Travelers Indemnity CompanycoreChannel Partner/ Reseller/ DistributorCommercial and personal insurance carrier. LR WINDSOR offers Travelers products for business and personal coverage.
• UnitedHealthcarecoreChannel Partner/ Reseller/ DistributorHealth insurance provider offering individual and group health coverage. LR WINDSOR offers UnitedHealthcare products.
• Unum GroupcoreChannel Partner/ Reseller/ DistributorEmployee benefits provider offering disability, life, and voluntary benefits. LR WINDSOR offers Unum products for group benefits.
• Independent Insurance Agents and Brokers of America (IIABA)minorStrategic or Co-development PartnerNational association supporting independent insurance agents with resources and advocacy.
• Independent Insurance Agents of IllinoisminorStrategic or Co-development PartnerState association representing independent insurance agents in Illinois.
• National Association of Insurance Financial Advisors (NAIFA)minorStrategic or Co-development PartnerProfessional association for insurance and financial advisors.
• Trusted ChoiceminorStrategic or Co-development PartnerBrand identity program for independent insurance agents emphasizing choice and advocacy.

Scale indicators3 records

Recent moves6 records

Expansion highlights4 records

Regional players

• Erie Insurance: Erie Insurance is a regional carrier with a strong independent-agent distribution model and is LR WINDSOR's flagship carrier partner; both share geographic concentration in the Midwest and a focus on personal auto/home with growing commercial.

Broad incumbents

• Brown & Brown, Inc. Brown & Brown is a large national insurance brokerage built through serial acquisition of independent agencies; it represents the institutional version of LR WINDSOR's multi-carrier, multi-line agency model.
• Allstate: Allstate operates a captive-agent model and increasingly a direct channel, competing with independent agencies like LR WINDSOR for Illinois personal lines customers.
• State Farm: State Farm is the largest U.S. personal-lines insurer with a captive-agent model that competes directly with LR WINDSOR in Illinois personal auto and home insurance.
• Arthur J. Gallagher & Co. Gallagher is a global insurance brokerage and risk management firm, also founded as an independent agency in the U.S. Midwest; it represents an end-state scale version of the LR WINDSOR model, with overlapping carrier partners and customer segments.

Direct peers

• AssuredPartners: AssuredPartners is a national independent insurance brokerage built by acquiring regional agencies, directly comparable to a rollup strategy LR WINDSOR could pursue and serving the same multi-line personal and commercial client base.
• Goosehead Insurance: Goosehead Insurance is a personal-lines-focused independent agency franchise offering comparative quotes across multiple carriers, comparable in customer segment and quote-comparison model to LR WINDSOR's personal lines business.
• Hub International: Hub International is a large North American insurance brokerage that represents multiple carriers and serves mid-market commercial and personal clients, mirroring LR WINDSOR's independent-agency model but at far greater scale and geographic reach.

Emerging players

• Next Insurance: Next Insurance is a digital-first SMB commercial carrier offering bindable online quotes for general liability, workers' comp, and professional liability, competing for the same small-business accounts LR WINDSOR places through carriers like CNA and Erie.
• Lemonade: Lemonade is a digital-first InsurTech carrier bypassing traditional agents, representing a structural competitive threat to LR WINDSOR's personal lines commission revenue.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/lrwindsor
• Facebookfacebook.com/LRWINDSOR
• LinkedInlinkedin.com/company/3731620

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Subsidiaries1 record

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 LR WINDSOR