Charles String, Inc. is an independent insurance agency that specializes in trucking. However, we do a bit more than just insurance.

We host the Truck Insurance YouTube channel, educating and consulting with truckers across the country.

We are heavily tech driven and very unconventional compared to the rest of the insurance clones. Our systems and processes are far ahead of any other agency out there and we are continually expanding our resources. It will blow your mind.

We are on a mission to make trucking insurance better, because it mostly sucks! It’s extremely complicated, riddled with archaic business practices, and no one seems to care enough about the truckers. As a result, there is a massive opportunity to shake things up in this industry and that is exactly what we are doing.

Our company is privately owned. We navigate our business the way we see fit, and the work we do is pretty amazing. Our customers love us because we serve them first, and foremost. Most don’t realize how much we actually do, and that’s perfectly fine, there’s nothing wrong with being a little humble.


We are looking for a Licensed Property and Casualty Insurance Agent who has experience in trucking and is interested in helping to grow our business.

DISCLAIMER: This is not your typical insurance agent position.

Our office hours are 9-5 Monday thru Friday. That said, we tend to put in the extra hours to get everything done and not leave our clients hanging. It’s not unusual to see emails being sent out at all hours of the night. We’re very serious about our mission. Our worth is measured by the success of our clients, not by commissions or premiums.

We are a powerful unit because our tools and collaboration are top notch. We share one email inbox, one phone line, and all of us help with every client. Our clients don’t have an agent, they legitimately have an agency. Everything we do is centered around the client experience and supporting their businesses. Our response times on quotes and service work is incredibly fast. The only way we succeed, is if our clients succeed.

Everyone contributes to our YouTube channel. We don’t waste a bunch of money on advertising or spend time cold calling to annoy people all day, begging shamelessly for their business. Instead, we create helpful and informative videos. People trust the content we put out there and the business comes to us. Our prospects are more like fans and our clients are like family.


  • Work from home, our office, outside, inside, abroad …wherever you can be available and focused is fine by us
  • Consult with prospects and clients about their trucking businesses to understand their insurance needs
  • Maintain industry knowledge and standards
  • Stay up to date on current events in transportation
  • Provide transparency and educate clients on policy options, regulations, etc.
  • Bind policies and assist with service work
  • Promote affiliate partners – we’ve got a vendor for anything a trucker could possibly need
  • We DO NOT upsell or push anything on our clients that they don’t need
  • Sometimes we might not be the best fit, but we always help in any way we can
  • Occasional travel to events and conferences, maybe twice a year and totally optional


We believe that people who truly care about their work, don’t need a decade of prior “experience” or an expensive degree. If you’re the right fit, it will be easy to tell. It’s hard to hide the passion for what you enjoy doing!

  • Licensed insurance agent in property and casualty. If you’re not licensed, get licensed. We will not entertain un-licensed applicants. Every agent here got their license while working at least one full time job. You can do it!
  • Knowledge of transportation regulations and insurance coverages as they pertain to trucking operations.
  • Your drive defines you. You are never satisfied and constantly want to improve – for yourself, and for our clients.
  • Highly adaptive. We make changes and implement them on the fly. You must be able to keep up.
  • Organized and task oriented. We’ve got some crazy good systems in place, and we get things done fast, really fast.
  • Mac and iOS skills. You’ll be using a MacBook Pro, a Mac desktop with at least 3 monitors and an iPhone…all company provided of course.
  • Concise. While communication skills are critical, being brief and to the point is equally important.
  • Optimistic, opportunistic, and realistic. You can stay positive and stay focused on long term goals even when the struggle is real.


  • Competitive $alary
    • We don’t do commissions. Our focus is helping our clients, no need for distractions.
  • Medical, Dental, and Vision
    • We have a top tier plan with a very low deductible and a great network…and it’s fully company paid!
  • 401k with company match
    • We’ll help you save for retirement if you’re into that kind of thing.
  • Unlimited Time Off
    • Some companies are “work hard, play hard.” We’re more like “work hard, work harder.” We understand that having a life outside of work is “healthy” so take time off when you need to and then get back to the mission. We’re all counting on one another.