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Infographic showing various Flex Facebook Contractor job openings in the United States as of August 2026, with employment types broken down into 71% Full Time, 9% Part Time, and 20% Contract. Highlights an 88% Physical, 1% Hybrid, and 11% Remote job distribution.

Experienced Sales Executive - Transportation

Cottingham & Butler

Madison, WI • On-site

Full-time, Contractor

Re-posted 26 days ago

Cottingham & Butler rating

8.6

Company rating: 8.6 out of 10

Based on 15 frontline employees who took The Breakroom Quiz

91st of 311 rated insurance

Job description

Cottingham & Butler Transportation Group provides first-class insurance solutions to over 2,500 trucking companies across the U.S. Our service extends beyond buying insurance to helping our clients with safety, claims, and compliance challenges. As the leading insurance broker in the transportation industry, we provide better solutions, better advice, and better results.

We are currently adding experienced transportation producers. Joining our sales team will allow you access to the markets, tools, and expertise needed to write more business. You will also work with a top-notch service team that will ensure that you retain more business. A bigger book of business = more money in your pocket! This position requires 3 years of experience in Transportation Insurance.

Here are a few things that set us apart:

  • Our Team. 300+ experienced professionals that specialize in the trucking industry and have the vision and expertise to help our clients clearly identify the risks they face and develop the necessary steps to mitigate or avoid them
  • Market Access. Our experience and reputation in the transportation industry give us the ability to secure the most competitive terms from the top insurance markets.
  • Our Solutions. We offer a full range of traditional and non-traditional insurance solutions, including in-house claims, safety management, and captive insurance services. We also offer an independent contractor platform and brokerage claims advocacy. The best part- the services aren't charged back to the producer.
  • Trucking Captives. We are the exclusive broker for 7 trucking captives, including the two largest in the world. There are over 245 captive members and a 99% retention rate in our captives.
  • Clients love us. They choose us because they see value in the services we offer and stay with us because we exceed their expectations. The Transportation Division has an average annual organic growth rate of 12.5% and our client retention is over 95%.

Ultimately, we like to win and have a track record of doing it year-over-year. Many of the best brokers in the nation have chosen to call Cottingham & Butler home and have built careers unlike anything in the industry. Here is a link to a highlight video from one of our National Sales Celebration Events: www.bit.ly/www.bit.ly/salesCB.

Pay & Benefits

  • Full salary + bonus
  • Most Benefits start Day 1
  • Medical, Dental, Vision Insurance
  • Flex Spending or HSA
  • 401(k) with company match
  • Profit-Sharing/ Defined Contribution (1-year waiting period)
  • PTO/ Paid Holidays
  • Company-paid ST and LT Disability
  • Maternity Leave/ Parental Leave
  • Company-paid Term Life/ Accidental Death Insurance

About Cottingham & Butler:

At Cottingham & Butler, we sell a promise to help our clients through life's toughest moments. To deliver on that promise, we aim to hire, train, and grow the best professionals in the industry. We look for people with an insatiable desire to succeed, are committed to growing, and thrive on challenges. Our culture is guided by the theme of "better every day" constantly pushing ourselves to be better than yesterday – that's who we are and what we believe in.

As an organization, we are tremendously optimistic about the future and have incredibly high expectations for our people and our performance. Our ability to grow as a company, fuels investments in new resources to better serve our clients and provide the amazing career opportunities our employees want and deserve. This is why we are a growth company and why we are committed to being better every day.

Want to learn more? Follow us on www.CottinghamButler.com | LinkedIn | Facebook

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