Midwest Insurance Group

What Midwest Insurance Group does

Midwest Insurance Group, Inc. (MIG) is a privately held independent insurance agency headquartered at 525 Main Street in Delafield, Wisconsin, with a secondary office in Mequon. Founded in 2000 by Jeremy Cardenas and operating as a first-generation agency, MIG sells personal and commercial property & casualty insurance, life and annuity products, and employee benefits to individuals, families, and businesses across southeastern Wisconsin. The company earns commission revenue by placing policies with select insurance carriers (including Erie Insurance) rather than underwriting risk itself, and it differentiates through vertical-specialist teams serving construction, manufacturing, wholesale distribution, restaurants/food & beverage, commercial real estate, non-profits, auto dealerships, auto aftermarket, and fitness/recreation businesses, in addition to personal lines (auto, home, umbrella, recreational vehicles, life, income protection, long-term care, annuities).

MIG operates a sales-led go-to-market model delivered through licensed agents in its two offices plus phone/remote consultation, with referral and association-driven demand generation. Pricing is quote-based and varies by risk profile, coverage needs, and carrier underwriting; revenue is structured as recurring annual commissions on policy placements and renewals. The company layers value-added risk management services onto its brokerage book, including the CSR24 client portal for 24/7 self-service, Midwest Connect (OSHA compliance, safety templates, HR toolkit), Midwest LMS (200+ training courses), an HR Hotline staffed by HR professionals, and hands-on loss control and claims advocacy services.

Ownership remains with founders and current leadership; the firm has no parent company, no external private equity or venture capital, and no disclosed subsidiaries. Leadership comprises Founder/Principal Jeremy Cardenas, VP of Business Development Steve Pape (joined 2002), Director of Operations/Managing Partner Crystal Benson, and Sales Director/Managing Partner Matt Wallace (27 years of industry experience). MIG was named a 2026 BizTimes Media Future 50 company, recognizing it among the fastest-growing privately-held companies in southeastern Wisconsin, and the firm has reportedly doubled in size over the past five years.

Name

Midwest Insurance Group

Legal name

Midwest Insurance Group, Inc.

Website

https://midwestinsurancegroup.com

Company type

Private

Founded year

2000

Operating status

Operating

Headcount range

11–50 employees

Short description

Midwest Insurance Group is a privately held independent insurance agency in Delafield, Wisconsin, selling personal, commercial, and employee benefits insurance to individuals and businesses across southeastern Wisconsin via vertical-specialist teams and carrier partnerships.

Ownership category

akta.pro rank

Product category

Insurance Brokerage

NAICS

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

SIC

Insurance Agents, Brokers & Service (6411), Life Insurance (6311), Accident & Health Insurance (6321)

akta.pro primary industry

Retail (Personal Lines) Insurance Brokerage (FSAEADAA)

akta.pro secondary industries

Fully Insured Small Group Plans (HLAEAAAB), Nonprofit / Social Services BOP (FSAJAFAM), Light Manufacturing / Small Industrial Package (FSAJAFAJ)

Keywords

• Commercial insurance brokerage
• Personal insurance agency
• Employee benefits consulting
• Risk management services
• Independent insurance agency

Headquarters

HQ city

Delafield

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: Midwest Insurance Group operates as an independent insurance agency earning commissions from insurance carriers for placing personal and commercial insurance policies. They work with select insurance companies to offer casualty and property insurance for businesses and individuals, earning revenue through policy sales and renewals.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels5 records

Core offering

Midwest Insurance Group is an independent insurance agency that places personal lines (auto, home, umbrella, life, recreational vehicles) and commercial lines (construction, manufacturing, restaurants, real estate, dealerships) insurance and employee benefits for individuals and businesses in southeastern Wisconsin. The firm earns commissions from multiple carrier partners and supplements policy placement with risk management, claims advocacy, HR consulting, and compliance training services delivered through proprietary client portals.

Product overview

Midwest Insurance Group operates as an independent insurance agency offering a comprehensive portfolio of personal insurance products (auto, homeowner's, umbrella, recreational vehicles, life, income protection, long-term care, and annuities) and business insurance products (construction, manufacturing, wholesale distribution, small business, restaurant/food & beverage, commercial real estate, non-profit, auto dealership, auto aftermarket, and fitness/sports/recreation). The company also provides employee benefits solutions including health plans, dental, disability, vision, life, FSAs, HSAs, HRAs, EAP, and voluntary benefits. Client service tools include CSR24 (24/7 policy management portal), Midwest Connect (compliance and safety resources), Midwest LMS (learning management system with 200+ courses), HR Hotline (HR consultation), and Loss Control and Claims Services. This is a services-based insurance agency rather than a technology product company.

Differentiator

Problem solved

Functional benefit

Products and services

• Auto Insurance Auto insurance covering bodily injury liability, collision, comprehensive, uninsured/underinsured motorist, property damage, and medical payments coverage for vehicles driven in Wisconsin.
• Homeowner's Insurance Home insurance combining dwelling protection, personal property, loss of use, and liability coverage in a single policy to protect homes, possessions, and families in Wisconsin.
• Umbrella Insurance Personal umbrella policies providing an extra layer of protection when underlying auto or home policy limits are exhausted, covering legal defense costs, jury awards, and long-term medical care.
• Recreational & Specialty Vehicles Insurance Insurance coverage for recreational vehicles including motorcycles, boats, mopeds, jet skis, ATVs, UTVs, RVs, campers, motor homes, travel trailers, golf carts, and classic/collector cars and trucks.
• Life Insurance Life insurance products including term life and permanent life insurance designed to replace lost income, pay off debts, pay funeral costs, continue family businesses, protect spouses' retirement plans, or fund children's education.
• Income Protection Stand-alone disability protection policies that supplement employer-provided coverage, designed to protect income-earning ability for mortgage payments, college tuition, and daily living expenses.
• Long Term Care Insurance Long-term care insurance designed to assist with costs of care when a person can no longer properly care for themselves due to illness, impairment, accident, or injury.
• Annuities Retirement planning products that ensure individuals do not outlive their retirement savings, providing financial management solutions for the descent from peak savings.
• Construction & Contractors Insurance Specialized insurance program for contractors including construction contract reviews, bid and performance bonds, contractor's errors and omissions, environmental liability, wrap-up coverage, employment practices liability, and cyber liability.
• Manufacturers Insurance Manufacturing niche-market program covering food and beverage, metal and steel, plastic, wood and furniture, equipment and machinery, paper and printing, and electronics manufacturing, with selling price valuation, product recall, consequential loss, and brands and labels coverage.
• Wholesale Distributors Insurance Insurance for distributors covering cost-containment programs, foreign products liability, contractual liabilities, and manufacturers' errors and omissions, designed for logistics, warehousing, and complex supply chain operations.
• Small Business Insurance Comprehensive coverage including commercial property insurance, general liability, employment practices liability, workers' compensation, cyber liability insurance, commercial auto, and professional liability insurance for Wisconsin small businesses.
• Restaurant, Food & Beverage Insurance Custom insurance programs for foodservice operations including affordable liquor liability, spoilage coverage, food contamination with business income, coverage for food trucks and trailers, and breakage of dishware and glasses.
• Commercial Real Estate Insurance Insurance for real estate organizations covering contingent liability, management and employee liability, fraud and crime, professional liability, environmental liability, standard and special property insurance, and business continuity.
• Non Profit & Social Services Insurance Specialized coverage for non-profit organizations including management liability for directors and officers, fiduciary liability, crime coverage, employee practices liability, physical and sexual molestation coverage, and volunteer accidental and medical expenses.
• Auto Dealership Insurance Specialized auto dealership insurance including mechanics errors and omissions, false pretense coverage, employment practices liability, dealer repair costs up to 100%, economic loss coverage for new auto inventory, and priority service through WATDA and ADAMM membership.
• Auto Aftermarket Insurance Insurance for auto repair shops covering mechanics errors and omissions, false pretense, employment practices liability, and no limit actual loss sustained coverage on customer autos.
• Fitness, Sports & Recreation Insurance Specialized coverage for fitness and recreation businesses including automatic off-season coverage adjustments, industry-targeted injury liability, professional liability for coaches and trainers, equipment repair and maintenance, and business continuity.
• Employee Benefits Health insurance and voluntary benefit products including traditional health plans (PPO, HMO, POS), fully-insured and self-funded options, dental, disability, vision, life, FSAs, HSAs, HRAs, EAP, and voluntary benefits.
• CSR24 Client Portal 24/7 online client portal providing access to policy information, electronic policy documents, vehicle and driver management, auto ID cards, certificates of insurance, and certificate holder list management.
• Midwest Connect Portal Comprehensive resource portal providing OSHA compliance tools, safety templates, toolbox talks, risk management resources, industry-specific compliance information, and HR compliance toolkit.
• Midwest LMS (Learning Management System) Learning Management System providing over 200 training courses including sexual harassment prevention and workplace safety courses, with mobile-ready access and employee completion tracking.
• HR Hotline HR professional consultation service available by phone or email, providing guidance on employee benefits, leaves of absence, wage and hour issues, discipline, terminations, recruiting, employee relations, workers' compensation, investigations, and performance management.
• Loss Control and Claims Services Hands-on assistance with OSHA compliance, training, accident investigation, plant inspection, claims advocacy, and experience modification rating evaluation and analysis.

Quantifiable outcome

• Named to 2026 BizTimes Media Future 50 list of fastest-growing privately-owned companies in southeastern Wisconsin
• +2 more outcomes

Named customers3 records

Segments8 records

Ideal customer profiles1 record

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature5 records

Partnerships

Six partnerships are on record, tiered minor and core.

• BizTimes Media / Metropolitan Milwaukee Association of Commerce (MMAC)minorGTM or Marketing Partner · 18 September 2026Partnership for the Future 50 program recognizing fastest-growing privately-owned companies in southeastern Wisconsin. The program is in its 37th year and honors companies demonstrating significant revenue and employment growth.
• Wisconsin Restaurant AssociationminorStrategic or Co-development PartnerMidwest Insurance Group is a member of the Wisconsin Restaurant Association, demonstrating commitment to staying current on industry concerns and providing specialized insurance solutions for restaurant and food service businesses.
• Tavern League of WisconsinminorStrategic or Co-development PartnerMembership in the Tavern League of Wisconsin enables MIG to provide informed guidance on state-level risks including liquor liability and dram shop law claims for tavern and bar clients.
• Wisconsin Automobile & Truck Dealers Association (WATDA)coreStrategic or Co-development PartnerMIG is a WATDA member offering customized auto dealership insurance policies, priority service, and unparalleled levels of coverage for automobile and truck dealers.
• Automobile Dealers Association of Mega Milwaukee (ADAMM)minorStrategic or Co-development PartnerPartnership with ADAMM provides additional dealership-focused insurance solutions and industry networking for auto dealers in the greater Milwaukee area.
• Erie InsurancecoreChannel Partner/ Reseller/ DistributorErie Insurance is one of the nation's leading auto and home insurers with an A.M. Best rating of A+ (Superior). MIG partners with Erie Insurance as one of their select carrier partners offering competitive auto and home insurance products.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Cottingham & Butler: Cottingham & Butler is a Midwest-based independent insurance brokerage and risk management firm with industry-specialized practices in construction, manufacturing, and food & beverage, directly comparable to Midwest Insurance Group's vertical coverage.
• The Horton Group: The Horton Group is a Midwest-based independent insurance, benefits, and risk management firm with vertical specialization, highly comparable in business model and product breadth to Midwest Insurance Group.
• Hausmann-Johnson Insurance: Hausmann-Johnson is a Wisconsin-based independent insurance and risk management agency serving businesses and individuals, closely matching Midwest Insurance Group in regional focus and brokerage model.
• M3 Insurance: M3 Insurance is a Wisconsin-based independent insurance agency offering personal, commercial, and employee benefits solutions with vertical specialization, directly comparable to Midwest Insurance Group in size, geography, and product mix.

Broad incumbents

• Brown & Brown: Brown & Brown is a large publicly traded insurance brokerage with national reach across commercial, personal, and benefits lines, representing a scaled incumbent that competes with Midwest Insurance Group for regional and mid-market commercial business.
• AssuredPartners: AssuredPartners is a large national insurance brokerage built through regional agency acquisitions, providing P&C, benefits, and risk management services that overlap with Midwest Insurance Group's offerings across multiple verticals.
• Hub International: Hub International is a large North American insurance brokerage offering commercial, personal, and benefits solutions through a vast agency network; competes broadly with Midwest Insurance Group for mid-market commercial accounts but operates at much greater scale.
• Arthur J. Gallagher & Co. Arthur J. Gallagher is a global insurance brokerage and risk management firm with a substantial middle-market and benefits practice, serving as a broad incumbent competitor to Midwest Insurance Group for commercial and employee benefits accounts.
• USI Insurance Services: USI Insurance Services is a large national brokerage delivering property & casualty, employee benefits, and specialty coverage with industry-segmented practices, directly competing with Midwest Insurance Group in the mid-market commercial and benefits space.
• NFP (an Aon company): NFP is a large insurance brokerage and consulting firm offering commercial, personal, and benefits solutions across the U.S., representing a scaled competitor that targets many of the same middle-market and benefits clients as Midwest Insurance Group.

Market position

Strengths5 records

Weaknesses4 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

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 Midwest Insurance Group