Remote Senior Commercial Insurance Agent

Trucker Path Insurance Inc

United States

Remote

USD 52,000 - 65,000

Full time

14 days+

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Benefits offered by this job

AI-First Innovation

Health Insurance

Paid Time Off

Discounted Gym Memberships

Paternity Leave

Employee Assistance Program

Team Building

Growth Opportunities

Tools To Do the Job

401(k) matching

Job summary

Trucker Path Insurance Inc is seeking a Senior Commercial Insurance Agent to lead a book of trucking insurance business. You will work remotely with Sales leadership to assess exposures, propose coverage, and manage client relationships across owner-operators and fleets.

The role emphasizes consultative selling, pipeline management, and understanding FMCSA/DOT requirements. A license is required and the compensation includes uncapped commissions and a generous OTE.

Qualifications

2+ years of commercial trucking insurance experience in producer, broker, agent, or account-facing role.
Active Property & Casualty insurance license.
Strong understanding of commercial trucking risks and FMCSA/DOT requirements.

Responsibilities

Build and grow a book of commercial trucking insurance through inbound opportunities, referrals, prospecting, and relationship development.
Consult with owner-operators, fleet owners, and transportation businesses to understand operations, exposures, loss history, and insurance needs.
Structure, quote, and present coverage solutions including commercial auto, motor truck cargo, general liability, occupational accident, and other trucking-related products.
Navigate carrier appetite, underwriting requirements, submissions, and market options to identify competitive solutions for clients.
Understand and advise clients on trucking-specific insurance requirements, including FMCSA regulations, DOT filings, and related compliance considerations to deliver an excellent client experience.
Maintain an organized, active sales pipeline and consistently follow opportunities through quote, bind, and renewal.

Skills

Pipeline management

Relationship development

Consultative selling

Outbound prospecting

Inbound opportunities handling

Education

Property & Casualty license

Tools

CRM systems

Quoting platforms

Agency management systems

Job description

Description

Who are We?

Trucker Path is a leading technology platform in the freight and logistics industry, trusted by more than one million drivers and carriers for navigation, load planning, and tools that help keep their businesses moving. Trucker Path Insurance (TPI) was built specifically for that community. We provide commercial insurance solutions designed around the unique risks facing truckers, owner-operators, and fleets. We're growing our national footprint and looking for experienced trucking insurance professionals who know this industry, understand its risks, and are ready to build a meaningful book of business.

What's the Job?

We're looking for a Senior Commercial Insurance Agent with hands-on experience in the commercial trucking insurance market. We're looking for someone who understands trucking risks, knows how to navigate the commercial insurance market, and can confidently advise clients on coverage for their businesses.

Reporting to the Vice President of Sales, you'll work with truckers, owner-operators, and fleet businesses to assess their exposures, identify coverage needs, navigate carrier options, and build insurance programs that protect their operations. You'll manage a combination of inbound opportunities and targeted outbound prospecting while developing a personal book of business and long-term client relationships.

Build and grow a book of commercial trucking insurance business through inbound opportunities, referrals, prospecting, and relationship development.
Consult with owner-operators, fleet owners, and transportation businesses to understand operations, exposures, loss history, and insurance needs.
Structure, quote, and present coverage solutions including commercial auto, motor truck cargo, general liability, occupational accident, and other trucking-related products.
Navigate carrier appetite, underwriting requirements, submissions, and market options to identify competitive solutions for clients.
Understand and advise clients on trucking-specific insurance requirements, including FMCSA regulations, DOT filings, and related compliance considerations to deliver an excellent client experience.
Maintain an organized, active sales pipeline and consistently follow opportunities through quote, bind, and renewal.

What’s the Work Location?

This is a fully remote role and can be based anywhere in the United States. You'll work closely with Sales Leadership, underwriting resources, and the broader TPI team through a highly collaborative remote environment.

What's the Earning Potential?

Our compensation structure rewards performance consistently. The base salary is estimated at $52,000–$65,000, based on the candidate's experience, qualifications, and local market.

Producers earn uncapped commissions paid monthly, with an average first-year OTE of approx. $100,000. Strong performers have the opportunity to earn significantly more.

Requirements

What Are We Looking For?

2+ years of commercial trucking insurance experience, ideally in a producer, broker, agent, or account-facing role.
Active Property & Casualty insurance license.
Strong understanding of commercial trucking risks and insurance products.
Working knowledge of FMCSA requirements, DOT filings, and transportation insurance requirements.
Demonstrated ability to develop relationships, assess client needs, and sell commercial insurance consultatively.
Experience working with insurance carriers, underwriters, quoting platforms, and agency management or CRM systems.
Strong pipeline management and follow-through.
Comfortable balancing inbound opportunities with proactive business development.

What Will Make You Stand Out?

Experience working with fleet, middle-market, or more complex trucking accounts.
Existing carrier relationships or strong knowledge of the trucking insurance marketplace.
Experience building and managing your own book of business.
Multi-state P&C licensing.
Strong knowledge of commercial auto underwriting and transportation risk.

Anything else? Absolutely! Benefits and Perks:

This is a place where every day we are inspired by our teammates, encouraging each other to be our best. The environment is friendly and supportive! And we feel it’s important to reward our team with competitive pay and benefits. Here are some of the highlights:

AI-First Innovation: We’re building toward becoming an AI-native company — and our employees are part of that journey. You’ll have access to leading AI tools, hands-on learning opportunities, and real-world exposure to how AI is transforming business. We believe the future belongs to those who learn it early — and we invest in helping you do exactly that.
Health Insurance: Only $100 per month for medical coverage for employee only! And the ability to add dependents or choose an alternative plan and receive a wellness credit to keep your costs down.
Paid Time Off: Work hard, play hard! A total of three weeks of time off during the calendar year.
Discounted Gym Memberships: Pay only $28 per month to join a gym! This discount program is available to all employees on our medical insurance plans. Stay fit while keeping more money in your wallet!
Paternity Leave: We support our team members as they grow their families! Once you qualify for FMLA, you are eligible to receive up to 6 weeks of paid paternity time to bond with a new child.
Employee Assistance Program: We are proud to offer free access to SupportLinc, a global platform that provides on-demand care as you navigate personal or professional challenges. This confidential and compassionate support system is available to you and your family members anytime you need help.
Team Building: We may work across time zones and countries, but we’re still united. We host a monthly schedule of team activities, quarterly town halls, open Q&A sessions, and other special events...so many fun ways for us to connect and support one another.
Growth Opportunities: When our people grow...we grow! We offer leadership training, development journeys for core teams, and coaching/mentoring opportunities. Constant growth and development are inherent in our culture.
Tools To Do the Job: We ensure you are hooked up with the tools, equipment, and systems you need. We begin the process? Prior to your start date, so you are ready to rock ‘n roll on your first day!
What Else: We provide a 401(k)-company match and 100% company-paid life/AD&D insurance/short-term disability. Our ultimate goal is to support you and your overall wellness.