Now Hiring - 160 Driving Academy - Enterprise Sales Representative in Chicago, IL

Full description of the position

Description:

About Us

As the largest state-licensed CDL training provider with over 150+ locations we teach individuals how to safely operate commercial vehicles and obtain their CDLs. Now we are helping trucking fleets nationwide to train, recruit, and retain safe, job-ready drivers. With operations in 40+ states and partnerships with some of America's top fleets, we're solving one of the industry's biggest challenges: the driver shortage. Role

Overview

We're seeking a B2B Sales Representative to build partnerships with trucking fleets, carriers, and logistics companies. Your mission: help fleets reduce hiring costs, improve driver retention, and ensure compliance by connecting them with our CDL training solutions. What You 'll Do

• Prospect and develop new business with trucking fleets and carriers.
• Build relationships with decision-makers (Executives, VPs, Directors, Sr Management).
• Conduct in-depth needs analysis to understand client pain points and offer appropriate product/service solutions
• Present and sell CDL training and driver recruitment solutions
• Negotiate and close partnership agreements.
• Stay updated on industry trends, competitive landscape, and market conditions
• Maintain accurate CRM records of sales activities, opportunities, and client interactions
• Manage existing accounts and identify upsell opportunities.
• Travel to meet with prospective clients & attend industry events/trade shows. What We Offer
• Competitive base salary +commission.
• Health, dental, vision, and 401(k)
• Paid time off & holidays.
• Expense reimbursement + travel opportunities.
• Growth and professional development. Why This Role Matters You'll be at the forefront of addressing the driver shortage by connecting fleets with a trusted, licensed CDL training provider. Every partnership you build helps carriers hire smarter, safer, and more cost-effectively. Apply Today and help us build the future of trucking.

Requirements

: What We 're Looking For

• 3+ years B2B sales experience (transportation, staffing, or workforce development preferred).
• Knowledge of trucking industry challenges (driver shortage, turnover, compliance).
• Executive-Level communicator confident pitching, presenting, and negotiation at the highest levels
• Relationship Builder with the ability to network & develop long-term relationships.
• Self-starter who thrives in a fast-paced, relationship-driven role.
• Ability to travel to meet prospective clients and attend events.