B2B Enterprise Sales Representative

Company: 160 Driving Academy
Location: Chicago
Posted on: February 14, 2026

Job Description:

Job Description Job Description 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. 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. 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.

Keywords: 160 Driving Academy, Wheaton , B2B Enterprise Sales Representative, Sales , Chicago, Illinois