2026-05-15 – Weekly Trucking Jobs : Remote trucking insurance roles available

Important Note: These jobs are posted in real-time and might expire. Please apply promptly.


This week, the job market’s buzzing with opportunities in the trucking insurance sector. There’s a pressing need for specialists in commercial trucking insurance, and some solid remote roles are available too. If you’re looking for flexibility or have a knack for insurance, now’s the time to explore.


This Week’s Jobs

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Madison, WI
    If you’re a licensed P&C agent wanting to specialize in commercial trucking insurance, this role is calling your name. Dive deep into the niche and make an impact.
    Apply Here

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Eau Claire, WI
    Another great opportunity for P&C agents focusing on commercial trucking insurance. A chance to build expertise and grow in a specialized field.
    Apply Here

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Rockford, IL
    Specialize in commercial trucking insurance with this role. Perfect for licensed P&C agents ready for a niche focus.
    Apply Here

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Milwaukee, WI
    Join a team dedicated to commercial trucking insurance. Licensed P&C agents can find a rewarding path here.
    Apply Here

  • Trucking / Transportation Insurance Agent
    Company: Prestige International Insurance Group, Inc. | Location: Fort Lauderdale, FL
    Prestige Trucking Insurance offers top-notch solutions. If you’ve got experience in the industry, this is a chance to step up.
    Apply Here

  • Trucking Insurance Account Manager
    Company: Prestige International Insurance Gr Inc | Location: Tamarac, FL
    This role is oriented towards service, with a strong focus on the insurance and trucking industry. Perfect for those with industry knowledge.
    Apply Here

  • Partner Senior Associate (Trucking Litigation)
    Company: Gerber Ciano Kelly Brady LLP | Location: Albany, NY
    Looking for an attorney or partner-level expertise in trucking litigation. This role serves central and upstate areas.
    Apply Here

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Fort Lauderdale, FL
    If you’re a licensed P&C agent, this role offers a chance to focus on commercial trucking insurance in a dynamic environment.
    Apply Here

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Chicago, IL
    For P&C agents looking to specialize, this role in Chicago presents a significant opportunity to grow in commercial trucking insurance.
    Apply Here

  • Commercial Trucking Insurance Specialist
    Company: ATG Recruiting | Location: Aurora, IL
    This position is for those who have a license in P&C and are eager to dive into the commercial trucking insurance field.
    Apply Here


Work From Anywhere (100% Verified)

This week’s remote roles offer flexibility for those who need it. Check out these positions where you can work from anywhere.

  • Commercial Insurance Underwriting Supervisor - Remote | WFH
    Company: Get It - Finance | Location: Arlington, TX
    Lead a team in the commercial trucking insurance space from the comfort of your home. A great chance to mentor and guide.
    Apply Here

  • Schedule Coordinator
    Company: D&C Haulage | Location: Miami Beach, FL
    Work remotely with D&C Haulage, a company specializing in petroleum fueling stations and more.
    Apply Here

  • Small Business Underwriter (Hybrid) Location: Bloomington, IN - Remote | WFH
    Company: Get It Recruit - Transportation | Location: Bloomington, IN
    This role lets you shape the future of commercial trucking insurance while working remotely.
    Apply Here

  • Small Business Underwriter (Hybrid) Location: Bloomington, IN - Remote | WFH
    Company: Get It Recruit - Transportation | Location: Bloomington, IN
    A crucial role for managing a commercial trucking business portfolio, all from home.
    Apply Here

  • Small Business Underwriter (Hybrid) - Remote | WFH
    Company: Get It - Executive | Location: Sioux City, IA
    Manage and grow a book of business in commercial trucking. Assess risk and underwrite policies remotely.
    Apply Here

  • Small Business Underwriter (Hybrid) Location: Bloomington, IN - Remote | WFH
    Company: Get It Recruit - Transportation | Location: Bloomington, IN
    Be at the heart of operations, managing a commercial trucking portfolio from anywhere.
    Apply Here

  • Small Business Underwriter - Remote | WFH
    Company: Get It Recruit - Transportation | Location: Bloomington, IN
    Imagine building a successful portfolio in commercial trucking insurance from your home office.
    Apply Here

  • Commercial Insurance Underwriting Supervisor - (Hybrid) - Remote | WFH
    Company: Get It - Executive | Location: Arlington, TX
    Mentor and oversee a team of underwriters in commercial trucking insurance, all while working remotely.
    Apply Here

  • Underwriting Supervisor - (Hybrid) - Remote -
    Company: Get It - Finance | Location: Knoxville, TN
    Lead and develop a team of underwriters specializing in commercial trucking insurance. Make an impact from anywhere.
    Apply Here

  • Underwriting Supervisor - (Hybrid) - Remote -
    Company: Get It - Finance | Location: Knoxville, TN
    Provide expert guidance and oversee complex cases in commercial trucking insurance, all from your home office.
    Apply Here


See all urgent needs jobs here: See Urgent Needs Jobs
Explore remote jobs here: See Remote Jobs


Finding the right fit can be a journey, but these opportunities might just be the next step in your career. Whether you’re looking to work from home or dive into a specialized role, there’s plenty to explore this week. Happy job hunting!

1 Like

I recently landed a remote role in insurance, and it felt like finding the last piece of a jigsaw puzzle — one tip: tailor your resume for each application; it makes a big difference. Those trucking insurance roles seem like gold right now, so I’d suggest hitting apply like it’s a hot sale on Black Friday.

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It’s definitely a hot time for remote trucking insurance roles. From my experience, a strong cover letter that highlights your specific skills and experiences related to commercial trucking can really set you apart. Just yesterday, I saw a position that was looking for someone with knowledge of risk assessment tools.

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