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Overview
Cottingham & Butler is a large, privately held U.S. insurance broker focused on property & casualty and employee benefits. It helps clients manage risk by assessing needs, designing and placing insurance programs with carrier partners, and providing ongoing advisory, service, and claims support. Compared with competitors, it differentiates itself through its independence (not owned by carriers), scale, and a promise of consistent, improved outcomes—articulated as Better Every Day: better advice, better service, and better ideas than peers. The company emphasizes challenging conventional wisdom, innovating its services, and improving client results as it grew from 1887 to become the 3rd largest independently held broker. Its goal is to deliver measurable value for clients every day, helping them reduce risk and optimize benefits while maintaining strong growth and industry expertise.
About Cottingham & Butler
Industries
Consulting
Financial Services
Company Size
501-1,000
Company Stage
N/A
Total Funding
N/A
Headquarters
Dubuque, Iowa
Founded
1987
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Simplify's Take
What believers are saying
- Hessling arrived from Gallagher Bassett North America, bringing scaled brokerage and claims-operating experience.
- July 2026 brought Mark Roling, Taylor Orton, and Ryan Butler into expanded P&C leadership roles.
- The Des Moines office and July 2026 recruitment signal continued Midwest expansion and client coverage gains.
What critics are saying
- Transportation clients face nuclear verdict and fraud-ring losses, directly highlighted for August 2026 summit speakers.
- Mike Hessling started January 19, 2026, making execution dependent on a new leadership structure.
- The 55-seat West Des Moines office needs rapid hiring; missed recruiting slows Midwest growth.
What makes Cottingham & Butler unique
- Cottingham & Butler is the 4th largest privately held U.S. insurance broker, according to its December 2025 announcement.
- Its transportation practice convenes 550 trucking executives at the 2026 Transportation Summit in Schaumburg.
- Its trucking compensation benchmark survey offers niche data, including tank and bulk segment breakouts.
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Benefits
Health Insurance
Dental Insurance
Vision Insurance
Health Savings Account/Flexible Spending Account
401(k) Company Match
Profit Sharing
Unlimited Paid Time Off
Paid Holidays
Company-paid ST and LT Disability
Maternity Leave
Parental Leave
Subsidized Parking
Company-paid Term Life/Accidental Death Insurance
Company News
People moves: Cottingham & Butler Names Hessling President; Blessing Named Office President of CRC Group Kansas City Operation. Cottingham & Butler Names Hessling President Cottingham & Butler, headquartered in Dubuque, Iowa, named Mike Hessling as president. Hessling joins Cottingham & Butler from Gallagher Bassett, where he served as CEO of North America. As president, Hessling develops and executes the company's strategic agenda, with a focus on continued growth and long-term planning. Before Gallagher Bassett, Hessling held roles at Bain & Company, Bridge Strategy Group, and Arthur Andersen. Blessing Named Office President of CRC Group Kansas City Operation CRC Group, headquartered in Charlotte, North Carolina, named Matt Blessing as office president in Kansas City, Missouri, where he will continue to lead the firm's Select binding operations. Blessing is responsible for overseeing underwriting strategy, talent development, and market expansion while supporting retail partners. Blessing brings nearly two decades of experience in underwriting and binding authority operations, with a background spanning underwriting management, portfolio development, and complex risk evaluation across multiple lines of business.
Cottingham & Butler is opening a new office in the Des Moines area.
Cottingham & Butler recently launched a survey for the 2022 edition of its Annual Trucking Compensation & Benefits Benchmark Survey Report, which includes the only comprehensive breakout of data for the tank/bulk segment.
Through its partnership with Cottingham & Butler, McLeod Express employees have access to the PerkSpot Employee Discount Program at no cost to them!
Cottingham & Butler is Hiring for 97 Jobs on Simplify!
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About Cottingham & Butler
Industries
Consulting
Financial Services
Company Size
501-1,000
Company Stage
N/A
Total Funding
N/A
Headquarters
Dubuque, Iowa
Founded
1987
Cottingham & Butler is Hiring for 97 Jobs on Simplify!
Find jobs on Simplify and start your career today