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Enterprise Sales Representative
Enterprise Sales Representative160 Driving Academy • Chicago, IL, US
Enterprise Sales Representative

Enterprise Sales Representative

160 Driving Academy • Chicago, IL, US
30+ days ago
Job type
  • Full-time
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.

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.
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    Enterprise Sales Representative • Chicago, IL, US