Who are We?

Trucker Path is a leading technology platform in the freight and logistics industry, trusted by more than one million monthly active users, including truck drivers and carriers, for navigation, load planning, and operational efficiency tools that keep their businesses moving.

Trucker Path Insurance is a sibling company to Trucker Path , established to transform how truckers, owner-operators, and fleets access commercial insurance. Leveraging deep industry expertise, technology, and a customer-first approach, TPI is focused on simplifying the insurance experience, delivering tailored coverage solutions, and building lasting relationships within the trucking community.

As we rapidly expand our national footprint, we are building a high-performing team to support our growth and establish TPI as a trusted leader in commercial trucking insurance. We offer a fast-paced, entrepreneurial environment where initiative, accountability, collaboration, and results are valued.

We are looking for a Commercial Insurance Producer II to help establish and grow our mid-fleet segment. This role offers a unique opportunity to build a new business function from the ground up, develop a strong pipeline of mid-sized trucking fleets, drive revenue growth, and potentially grow into a Team Lead role as the segment expands. Reporting to the Vice President of Sales, you will help mid-sized fleets understand their exposures and build insurance programs that protect their operations.

Expectations

• Partner with Sales Leadership to design and refine the segment’s outreach approach and sales process, and capture what works so the producers who follow can ramp quickly.
• Prospect mid-sized fleets through targeted outbound outreach, and work inbound opportunities and referrals, to grow a personal book of business and lasting client relationships.
• Consult with fleet owners and transportation businesses to understand their operations, exposures, loss history, and insurance needs.
• Work across carrier partnerships, navigating appetite, underwriting requirements, and submissions to find competitive solutions for your clients.
• Advise clients on trucking-specific requirements, including FMCSA regulations, DOT filings, and related compliance, to deliver a smooth client experience.
• Demonstrate ownership and leadership potential by helping build the segment’s foundation and positioning yourself for future team lead opportunities as the team grows.
• Stay current on market conditions, coverage changes, and industry requirements, with support from our training team.

• 2+ years of commercial trucking insurance experience in a producer, broker, agent, or other account-facing role.
• An active Property & Casualty license (single or multi-state).
• Working knowledge of FMCSA requirements, DOT filings, and transportation insurance requirements.
• Comfort with proactive outbound business development, and a track record of building your own opportunities.
• Experience with carriers, underwriters, quoting platforms, and agency management or CRM systems, and confidence moving efficiently between several of them at once.
• Strong pipeline management and follow-through.

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. 

Join our growing team and let’s have fun building this business together!