Job Title: Transportation Account Executive

Location: Chicago IL (Hybrid Training then Fully Remote!)

About the Role:

We are seeking a motivated and entrepreneurial Transportation Account Executive to grow our commercial transportation insurance division. This role focuses on developing new business within the trucking and logistics industry while maintaining strong client relationships.

This is a remote opportunity with uncapped earning potential and access to a support team across sales, marketing, and operations.

Key Responsibilities:

• Build and manage a strong sales pipeline within the transportation industry
• Develop relationships with trucking companies, owner-operators, and fleet managers
• Generate new business through networking, referrals, and existing relationships
• Manage the full sales cycle: prospecting, quoting, closing, and renewing accounts
• Collaborate with internal teams and external partners to place business effectively
• Oversee submissions, quoting, and policy binding for accuracy and profitability
• Maintain client relationships and provide ongoing service support
• Stay up to date on insurance products, industry trends, and market changes
• Identify cross-selling opportunities across other insurance lines

Qualifications:

• Active Property & Casualty (P&C) insurance license (required)
• Strong sales and relationship-building skills
• Self-motivated with an entrepreneurial mindset
• Excellent communication and organizational abilities
• Ability to thrive in a fast-paced environment

Preferred:

• Experience in transportation or trucking insurance
• Background in insurance sales or commercial lines
• Familiarity with CRM or agency systems (e.g., Salesforce, AMS360)

Compensation:

• Base salary + uncapped commission + bonuses
• Total earning potential: $50K - $200K+

Benefits:

• Full medical, dental, and vision benefits
• 401(k) with match
• PTO and paid holidays
• Sales incentives and bonus programs
• Ongoing training and career growth opportunities

All qualified applicants will receive consideration for employment without regard to race, color, national origin, age, ancestry, religion, sex, sexual orientation, gender identity, gender expression, marital status, disability, medical condition, genetic information, pregnancy, or military or veteran status. We consider all qualified applicants, including those with criminal histories, in a manner consistent with state and local laws, including the California Fair Chance Act, City of Los Angeles' Fair Chance Initiative for Hiring Ordinance, and Los Angeles County Fair Chance Ordinance.