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Trucking Insurance Jobs (NOW HIRING)

HDVI

Physical Damage Adjuster

Greenville, SC · Remote

Technology meets Insurance. HDVI brings telematics, software and data together with commercial trucking insurance, taking transportation insurance and fleet risk management to the next level. Our ...

HDVI

Liability Adjuster

Greenville, SC · Remote

Technology meets Insurance. HDVI brings telematics, software and data together with commercial trucking insurance, taking transportation insurance and fleet risk management to the next level. Our ...

HDVI

Physical Damage Adjuster

Spartanburg, SC · On-site +1

Technology meets Insurance. HDVI brings telematics, software and data together with commercial trucking insurance, taking transportation insurance and fleet risk management to the next level. Our ...

Cottingham & Butler

Inside Sales Executive

Dubuque, IA · On-site

Inside Trucking Insurance Sales Cottingham & Butler is one of the largest insurance brokerage firms in the nation. We specialize in trucking insurance solutions with top tier programs for all size ...

Cottingham & Butler

Inside Sales Executive

Dubuque, IA · On-site

Inside Trucking Insurance Sales Cottingham & Butler is one of the largest insurance brokerage firms in the nation. We specialize in trucking insurance solutions with top tier programs for all size ...

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How much do trucking insurance jobs pay per year?

As of Aug 12, 2026, the average yearly pay for trucking insurance in the United States is $65,022.00, according to ZipRecruiter salary data. Most workers in this role earn between $44,500.00 and $77,000.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in trucking insurance?

To thrive in Trucking Insurance, you need a solid understanding of risk management, transportation regulations, commercial insurance policies, and strong analytical skills, often supported by a relevant degree or insurance licensure. Familiarity with insurance management software (such as AMS or Vertafore), quoting platforms, and regulatory compliance tools is highly beneficial. Strong customer service, negotiation, and problem-solving abilities help you build lasting relationships with trucking clients and carriers. These competencies are vital for navigating industry complexities, ensuring policy accuracy, and delivering tailored insurance solutions that protect clients' assets and operations.

What is trucking insurance?

A Trucking Insurance job involves selling, managing, and servicing insurance policies for commercial trucking businesses. Professionals in this field assess risk, provide coverage options, and ensure trucking companies comply with legal and financial requirements. They may work for insurance agencies, brokers, or as independent agents, helping clients protect their assets and operations. Responsibilities often include underwriting policies, handling claims, and advising trucking businesses on risk management strategies.

What are the most common challenges faced by professionals in trucking insurance?

Professionals in Trucking Insurance often encounter challenges such as staying updated with rapidly changing transportation regulations, managing claims involving large-scale property or cargo losses, and helping clients navigate complex coverage options. Balancing the needs of trucking companies with underwriting requirements and risk mitigation strategies requires attention to detail and resourcefulness. Additionally, responding quickly to claims and providing proactive risk management advice are key expectations in this fast-paced environment. However, overcoming these challenges helps build strong client relationships and enhances expertise in a niche insurance sector.

More about Trucking Insurance jobs
What cities are hiring for Trucking Insurance jobs? Cities with the most Trucking Insurance job openings:
What are the most commonly searched types of Trucking Insurance jobs? The most popular types of Trucking Insurance jobs are:
What states have the most Trucking Insurance jobs? States with the most job openings for Trucking Insurance jobs include:
What job categories do people searching Trucking Insurance jobs look for? The top searched job categories for Trucking Insurance jobs are:
Trucking Insurance jobs near you
Infographic showing various Trucking Insurance job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $65,022 per year, or $31.3 per hour.

Sales Representative Property and Casualty License 1099

Prestige International Insurance Gr Inc

Pompano Beach, FL • Remote

$150K - $350K/yr

Full-time

Posted 21 days ago

Job description

This is a Independent Contract (1099) role with Uncap Potential

Position Summary:

The Sales Representative is responsible for developing new business and managing client relationships within the trucking and transportation industry. This role focuses on identifying client needs, providing tailored insurance solutions, and driving revenue growth while delivering exceptional customer service. The ideal candidate is licensed, self motivated, and knowledgeable in commercial trucking insurance products. This is a Independent Contract role

Essential Duties and Responsibilities:

  • Develop and maintain relationships with trucking and transportation clients.
  • Identify client insurance needs and recommend appropriate coverage solutions.
  • Generate new business through outbound sales efforts, referrals, and inbound leads.
  • Leverage company technology, CRM, and support systems to manage leads and client accounts.
  • Educate clients on policy coverage, exclusions, and risk management strategies.
  • Stay informed on industry trends, regulatory changes, and coverage requirements that affect the trucking businesses.
  • Collaborate with underwriting, customer service, and claims teams to ensure seamless client onboarding and servicing.
  • Meet or exceed individual sales goals and performance metrics.
  • Maintain accurate documentation of sales activities and client communications.
  • Provide ongoing support to clients throughout the policy lifecycle, including renewals and coverage updates.

Knowledge / Skills / Abilities (KSA’s):

  • Sales & Negotiation Skills – Ability to prospect, qualify, present, and close insurance opportunities through consultative selling, objection handling, and effective negotiation techniques.
  • Client‑Focused Mindset – Ability to understand client needs, provide tailored insurance solutions, and deliver value‑driven service throughout the policy lifecycle to promote retention and long‑term relationships.
  • Insurance Products & Industry Knowledge – Working knowledge of commercial trucking insurance products, policy structures, coverage options, exclusions, and regulatory considerations affecting transportation businesses.
  • Communication Skills – Ability to communicate clearly, confidently, and professionally with clients, carriers, and internal teams through verbal discussions, written correspondence, and virtual meetings.
  • Client & Relationship Management Skill in developing trust‑based relationships with clients, prospects, and partners through consistent follow‑up, professionalism, and customer advocacy.
  • Time Management & Organizational Skills – Ability to manage multiple leads, accounts, and follow-ups while meeting deadlines, sales targets, and documentation requirements.
  • Problem‑Solving Capabilities – Ability to assess client situations, respond to objections or changes, and adapt sales strategies based on client needs, market conditions, or regulatory changes.
  • Attention to Detail & Compliance Awareness – Ability to accurately document sales activities, ensure policy accuracy, and adhere to licensing, regulatory, and company compliance standards.
  • Technology & Systems Proficiency – Ability to effectively use CRM systems, agency management platforms, and sales tools to track leads, manage accounts, and monitor performance metrics.
  • Professionalism & Accountability – Demonstrated reliability, integrity, and accountability in meeting sales objectives, following through on commitments, and representing Prestige Trucking Insurance professionally

Minimum Qualifications:

Required:

  • Active Property & Casualty Insurance License, Florida 2-20 License
  • Proven experience in insurance sales
  • Excellent verbal and written communication skills
  • Strong interpersonal and relationship-building abilities
  • Self-motivated, results-driven, and able to work independently or as part of a team

Preferred:

  • Experience working with trucking, transportation, or logistics clients
  • Familiarity with agency management systems or CRM platforms Key Competencies
  • Sales and negotiation skills
  • Client-focused mindset
  • Time management and organization
  • Problem-solving and adaptability
  • Attention to detail and compliance awareness

Physical Demands and Work Environment:

  • On‑site position
  • Office‑based with standard business hours
  • Use of computer systems, phones, and virtual meeting platforms