Full-Time

Captive Consultant

Property & Casualty

 Cottingham & Butler

Cottingham & Butler

501-1,000 employees

Independent insurance broker, P&C and benefits

No salary listed

Dubuque, IA, USA

In Person

Category
Finance & Banking (1)
Requirements
  • Bachelor’s degree in Risk Management, Finance, Insurance, or a related field (advanced degree or CPCU/ARM designation preferred)
  • 5+ years of experience in P&C insurance, risk management, or captive consulting
  • Strong understanding of insurance regulations, captive structures, and alternative risk financing
  • Excellent analytical, communication, and client relationship management skills
  • Ability to work independently and collaboratively in a fast-paced, client-focused environment
  • Proficiency in financial modeling tools and insurance management software
Responsibilities
  • Consult with clients to evaluate risk exposures and determine the feasibility of captive insurance solutions for P&C coverage
  • Conduct financial modeling, cost-benefit analysis, and risk retention studies to support captive formation and ongoing growth
  • Collaborate with legal, actuarial, and tax professionals to ensure compliance with regulatory and jurisdictional requirements
  • Monitor captive performance, analyze claims data, and recommend adjustments to optimize risk financing strategies
  • Provide ongoing advisory services, including annual reviews, board reporting, and strategic planning for captive evolution
  • Stay current on industry trends, regulatory changes, and emerging risks in the P&C insurance landscape
Desired Qualifications
  • Advanced degree or CPCU/ARM designation preferred

Cottingham & Butler is one of the largest privately held insurance brokers in the United States, specializing in property & casualty and employee benefits solutions. The company helps clients by assessing risk, recommending coverage, and placing policies with a network of insurance carriers, supported by advisory services from a nationwide team. Unlike many brokers, it is privately owned and emphasizes independent thinking and continuous improvement—challenging conventional wisdom to deliver better advice, better service, and better ideas every day. Its long-running growth since 1887 reflects a focus on practical, client-focused insurance solutions and professional service.

Company Size

501-1,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Dubuque, Iowa

Founded

1987

Simplify Jobs

Simplify's Take

What believers are saying

  • Mike Hessling appointed president January 19, 2026, drives growth strategy.
  • Opening Des Moines office expands Midwest trucking insurance presence.
  • Advises safety tech to counter 36% small fleet cost surge over 8 years.

What critics are saying

  • Hessling's growth shift diverts focus from trucking clients in 6-12 months.
  • Des Moines expansion loses share to HUB International's networks immediately.
  • CRC Group's Blessing captures trucking partners via faster underwriting now.

What makes Cottingham & Butler unique

  • Cottingham & Butler ranks 3rd largest private independent broker since 1887.
  • Launched 2022 Trucking Compensation Survey with tank/bulk data breakout.
  • Acquired Perspective Consulting Partners to expand insurance consulting.

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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

Insurance Journal
Jan 22nd, 2026
People Moves: Cottingham & Butler Names Hessling President; Blessing Named Office President of CRC Group Kansas City Operation

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.

QueenB Radio
Mar 11th, 2025
Cottingham & Butler opening Des Moines-area office

Cottingham & Butler is opening a new office in the Des Moines area.

Bulk Transporter
Feb 9th, 2022
Cottingham & Butler, Inc. launched survey for the 2022 edition of Annual Trucking Compensation & Benefits Benchmark Survey Report on Jan 9th 22'.

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.

McLeod Express
Jan 6th, 2022
Mcleod Express, Llc partners with Cottingham & Butler, Inc.

Through its partnership with Cottingham & Butler, McLeod Express employees have access to the PerkSpot Employee Discount Program at no cost to them!