R&R Insurance Services

What R&R Insurance Services does

R&R Insurance Services, Inc. is an independently owned insurance agency founded in 1975 and headquartered in Waukesha, Wisconsin, serving over 7,000 commercial clients across the Midwest and nationally. The firm operates four primary business units: Business Insurance (commercial lines including property and casualty, workers compensation, general liability, executive risk, cyber, surety bonds, and M&A insurance), Employee Benefits and Health Insurance (including the proprietary WellCompForLife integrated wellness/workers comp program), Personal Insurance (home, auto, Medicare), and Financial Services (life insurance, buy-sell agreements, business continuation). It also operates a Professional Services Division offering risk management consulting, loss prevention, claims and litigation management, data analytics, client training, and due diligence risk consulting across 24+ industry verticals including construction, manufacturing, healthcare, transportation, education, municipalities, and emerging segments like technology/cyber and temporary staffing.

The firm generates revenue primarily through brokerage commissions earned by placing business with multiple top-rated national and regional insurance carriers, supplemented by fee-based risk management and professional services. Go-to-market is sales-led through licensed brokers and dedicated vertical specialists, supported by direct phone/email outreach, a website quote-request funnel (myknowledgebroker.com), educational webinars, industry association partnerships (League of Wisconsin Municipalities, Wisconsin REALTORS Association), and referral networks. Proprietary technology includes ModMaster (workers compensation MOD reporting), PASSPORT (encrypted M&A data sharing), CSR-24 (24-hour certificate of insurance access), and the Risk Management Center (safety and program administration platform). International coverage is delivered through the Assurex Global partnership, providing access to 500+ offices in 80+ countries.

R&R has pursued selective inorganic growth, completing three acquisitions between 2016 and 2018 (Frett Barrington, R&R Wealth Management, Hanson Benefits) and launching a dedicated Cyber Division in 2018. The firm has earned sustained industry recognition including multiple Wisconsin REALTORS Association awards (2018-2019), the WELCOA Gold Well Workplace Award (2025), and the WCWI Mental Health in the Workplace Certificate (2026), reflecting investment in workplace culture and integrated wellness offerings.

Name

R&R Insurance Services

Legal name

R&R Insurance Services, Inc.

Website

https://myknowledgebroker.com

Company type

Private

Founded year

1975

Operating status

Operating

Headcount range

51–100 employees

Short description

R&R Insurance Services is an independently owned insurance agency founded in 1975 in Waukesha, Wisconsin, providing business insurance, employee benefits, personal insurance, and financial services to over 7,000 commercial clients across 24+ industry verticals in the Midwest.

Ownership category

akta.pro rank

Product category

Commercial Insurance Brokerage and Risk Management Services

NAICS

Agencies, Brokerages, and Other Insurance Related Activities (5242), Insurance Agencies and Brokerages (524210), Insurance Agencies and Brokerages (52421), Other Insurance Related Activities (52429)

SIC

Insurance Agents, Brokers & Service (6411), Fire, Marine & Casualty Insurance (6331), Accident & Health Insurance (6321)

akta.pro primary industry

Professional Liability (E&O) (FSAJAGAC)

akta.pro secondary industry

Directors & Officers (D&O) Liability (FSAJADAF)

Keywords

• Commercial insurance brokerage
• Employee benefits administration
• Personal lines insurance
• Risk management consulting
• Surety bond services

Headquarters

HQ city

Waukesha

HQ country

United States

HQ region

North America

Offices1 record

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 Brokerage Commissions: R&R Insurance operates as an independent insurance agency earning commissions from insurance carriers for placing business. They represent multiple top-rated national and regional insurance carriers and earn revenue through brokerage commissions on commercial and personal insurance policies.
2. Risk Management and Professional Services: Additional revenue streams from risk management consulting, loss prevention services, claims management, client training and education, and due diligence risk consulting services provided to clients across various industries.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels5 records

Core offering

R&R Insurance Services is an independent insurance agency that places business and personal insurance, employee benefits, surety bonds, and financial services products on behalf of clients through multiple top-rated national and regional carriers. The agency augments placement with in-house risk management professional services (loss prevention, claims management, due diligence consulting) and proprietary technology tools (ModMaster, PASSPORT, CSR-24, Risk Management Center, WellCompForLife). Premium pricing and carrier selection are quote-based and tailored to the insured's industry, risk profile, and coverage needs.

Product overview

R&R Insurance Services is an independent insurance agency offering a comprehensive portfolio of insurance and risk management products and services. The core offering consists of Business Insurance products (Property & Casualty, Workers Compensation, General Liability, Executive Risk, Cyber Insurance, and Surety Bonds) and Personal Insurance (Home, Auto, Medicare). Employee Benefits services include Health Insurance, WellCompForLife wellness programs, and Voluntary Benefits. The company also provides specialized services through its Professional Services Division offering Claims & Litigation Management, Loss Prevention, Data Analytics, and Due Diligence Risk Consulting. Proprietary tools include ModMaster for MOD reporting, PASSPORT for M&A data management, and CSR-24 for certificate management. International coverage is available through Assurex Global partnership.

Differentiator

Problem solved

Functional benefit

Products and services

• Property & Casualty Insurance Commercial coverage that protects businesses against loss or damage to business locations, contents, and property of others in their care. Targeted at commercial clients across R&R's 24+ industry verticals.
• Workers Compensation Insurance Coverage protecting workers for on-the-job injuries, providing lost wages, medical expenses, and legal fee coverage. Targeted at commercial clients, with active MOD factor evaluation and managed care support.
• General Liability Insurance Protection against bodily injury, property damage, and personal injury claims for businesses, often combined with property insurance in a Business Owners Policy.
• Executive Risk Insurance Coverage protecting executives, directors, and officers against liability exposures including D&O, Professional Liability, Employment Practices Liability, and Fiduciary Liability.
• Umbrella Liability Insurance Additional liability protection layer extending coverage when primary policy limits are exceeded, for commercial clients.
• Surety Bonds Full range of surety bonds including Contract Bonds, Commercial Bonds, and Court Bonds served by an experienced bonding team.
• Cyber Insurance Coverage protecting businesses from cyber threats including viruses, malware, cyber extortion, data breaches, identity theft, and social engineering attacks.
• Mergers & Acquisitions Insurance Specialized risk analysis and insurance broker expertise for company transitions, including Representations and Warranties Coverage, Tax Liability Coverage, and Loss Mitigation Coverage.
• Captive Insurance Alternative risk solutions including Single Parent Captives, Group Programs, Rent-A-Captives, Enterprise Risk Captives (831 B), Domestic and Off-Shore Captives for commercial clients.
• Building Ordinance Coverage Coverage for undamaged portion of building, demolition costs, and increased cost of construction when buildings must conform to municipal codes.
• Employee Dishonesty Protection Coverage protecting businesses against losses from fraudulent acts by employees including false invoices, payroll fraud, and embezzlement.
• Equipment Breakdown Coverage Coverage for sudden and accidental breakdown of electrical, mechanical, refrigeration, and HVAC equipment excluding standard perils like fire.
• Business Succession Planning Long-term planning services including buy-sell agreements, estate planning, key person insurance, and wealth management for business owners.
• Risk Management Services Professional services including risk management consulting, loss prevention, claims management, and predictive analytics for enterprise risk management.
• International Capabilities Global insurance coverage through Assurex Global partnership, providing international risk placement capability for commercial clients.
• Personal Insurance Individual coverage for families and consumers including Home Insurance, Auto Insurance, Personal Umbrella, Identity Theft, Flood Insurance, and Medicare.
• Employee Benefits Health insurance and employee benefits including Affordable Care Act compliance, Wellness programs, Self-Funded Health Insurance, HRAs, HSAs, and Voluntary Benefits for employer clients.
• WellCompForLife Integrated wellness and workers compensation program addressing obesity, workplace injuries, and aging workforce through prevention and injury management services.
• Voluntary Benefits Employee-selectable benefits including Group Dental, Vision, Life, Disability, Critical Illness, Accident, and Home & Auto Insurance.
• Financial Services Personal and business financial products including Life Insurance, Buy-Sell Agreements, Business Continuation, Long Term Care Insurance, and Mortgage Protection.
• ModMaster Proprietary workers compensation Experience Modification Factor (MOD) evaluation and monitoring tool that helps clients understand and improve their MOD factors to lower insurance premiums.
• PASSPORT Proprietary information management system providing encryption and firewall capabilities to protect and selectively share data in a confidential manner during mergers and acquisitions.
• CSR-24 24-hour online certificate access system allowing commercial clients to request and obtain certificates of insurance anytime.

Quantifiable outcome

• Over 7,000 commercial clients served as independent agency
• +6 more outcomes

Named customers16 records

Segments5 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature4 records

Partnerships

Three partnerships are on record, tiered core and minor.

• Assurex GlobalcoreStrategic or Co-development Partner · 1 January 1954Assurex Global is the world's largest privately held brokerage group with over $23 billion in premium volume and more than 500 partner office locations in 80+ countries on six continents. Founded in 1954 and headquartered in Columbus, Ohio, Assurex Global provides R&R Insurance with international capabilities to serve clients with global coverage needs. R&R is the only Assurex Global domiciled agency in Wisconsin.
• League of Wisconsin Municipalities (LWMMI)coreStrategic or Co-development PartnerR&R Insurance is an insurance consulting and risk management partner of the League of Wisconsin Municipalities (LWMMI). LWMMI was established in 1898 to work for the common good of cities and villages, providing a mutual insurance program with broad specialized coverages, competitive pricing, and specialized services in municipal loss prevention, claims, policy service, audit and consultation.
• JacksonLewisminorImplementation/ SI/ Consulting PartnerJacksonLewis is a resource partner law firm that provides R&R Insurance with consolidated information on health care reform and regulatory compliance matters, particularly regarding the Patient Protection and Affordable Care Act (PPACA).

Scale indicators5 records

Recent moves6 records

Expansion highlights6 records

Market position

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

• YouTubeyoutube.com/user/RRInsurance
• Xx.com/my_rrinsurance
• Facebookfacebook.com/RRInsuranceServices

Revenue estimate

Valuation estimate

Number of profiles

Profiles9 records

Funding overview

Funding rounds

Investors

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

M&A3 records

Investments

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

Frequently asked questions about R&R Insurance Services