Sales Executive - Transportation Insurance

Compensation: 1099 Independent Contractor | $200k-$300k Income Potential Location: Nashville, TN (Local preferred; Remote within the US Southeast Region considered for candidates with a trucking insurance background only)About the OpportunityOur client is a family-owned insurance agency specializing in trucking and transportation risk solutions. They provide individualized, premier trucking insurance packages in Tennessee and throughout the Southeast and Midwest US. The firm is expanding its sales team and seeking a driven Sales Executive who thrives in a performance-based environment and wants full ownership of their book of business.This is an ideal opportunity for a transportation insurance producer who wants autonomy, strong carrier relationships, provided leads from State programs, and the ability to build long-term residual income. Key ResponsibilitiesProspect and acquire new trucking and transportation clients (target accounts: 50–500 power units) through cold calling, networking, referrals, email outreach, field visits, and lead follow-up.Leverage State-provided leads while developing additional business through your own pipeline efforts.Build and maintain strong relationships with clients to generate renewals, cross-sell opportunities, and long-term partnerships.Negotiate rates, terms, and coverage structures with both clients and carriers to secure profitable placements.Prepare and manage submissions for market presentation to carriers.Own and manage your book of business, including renewals and account growth. As your book expands, additional support staff will be added.Operate independently in a fully remote environment, setting your own schedule and managing your workload.Requirements & QualificationsPrior experience in transportation/trucking insurance sales strongly preferred (will consider highly motivated sales professionals open to training).Strong prospecting, negotiation, and communication skills. Has experience building a book of business from scratch.Self-motivated, disciplined, and comfortable operating in a high-risk/high-reward, commission-driven compensation structure (they are open to providing guaranteed pay or base salary during ramp-up period, flexible based on individual needs) Familiarity with trucking insurance markets, underwriting requirements, and industry tools is preferred.Active Property & Casualty (P&C) insurance license required (or the desire & ability to get one) Existing book of business is a significant plus, but not required (no non-compete restrictions).Ability to work independently from home with a reliable phone and computer setup.Willingness to operate as a 1099 independent contractor and manage associated tax responsibilities.What Success Looks LikeBuilding a strong, recurring revenue book of transportation accountsDeveloping carrier relationships that allow competitive market accessCreating long-term client partnerships in the 50–500 unit trucking spaceGenerating significant uncapped commission incomeType: Direct HireCategory: SalesDate Posted: 2026-06-01