Full-Time

Entry Level Sales Executive

Trucking

 Cottingham & Butler

Cottingham & Butler

501-1,000 employees

Independent insurance broker, P&C and benefits

No salary listed

Dubuque, IA, USA

In Person

Category
Sales & Account Management (1)
Required Skills
Sales
Requirements
  • Candidates must be located in Dubuque, Iowa (headquarters) and be eligible to work in the United States.
  • Entry-level sales orientation with 0-3 years of sales experience, including soon-to-be college graduates or recent graduates.
  • Motivation by financial rewards and ability to achieve substantial earnings.
  • Strong communication and relationship-building skills; ability to learn quickly and become a trusted advisor to company leaders.
Responsibilities
  • Learn the business and become a trusted advisor to company leaders.
  • Identify, qualify, and close prospects.
  • Manage and retain your book of business and actively work towards its growth to unlock substantial financial growth.
  • Strategize and develop customized solutions for clients, leveraging available programs to deliver services that exceed client expectations.
  • Cultivate strong relationships with top decision makers, ensuring long-term client retention.
  • Collaborate with our service team to create compelling proposals and deliver impactful presentations to clients and prospects.
  • Earn relevant designations and stay up-to-date on continuing education credits provided by the company to enhance your professional growth and earning potential.

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!