Sales Director/Executive of Drayage

Director of Drayage Sales / Enterprise Sales Executive

Location: Itasca, IL (Hybrid/Remote for the right candidate)
Reports To: Executive Leadership
Compensation: Base Salary: $85,000–$150,000 + Performance Incentives (depending on experience)

Company Overview

Our client is a privately held transportation brokerage that has been serving the logistics industry for more than 26 years. Founded after building and selling a successful asset-based trucking company, the organization has developed a national reputation as one of the premier drayage specialists in North America.

Today the company generates approximately:

• 50% Drayage
• 40% Truckload
• 10% LTL, Partial, Expedited & Other Modes

Position Summary

We are looking for a seasoned Drayage Sales Executive who understands the ocean container marketplace and can help accelerate the company's growth throughout North America.

This is not an inside sales role.

The company is seeking someone who enjoys opening doors, building executive relationships, and developing new business with importers, exporters, freight forwarders, and strategic shipping organizations.

The ideal candidate has built credibility within the drayage industry and possesses relationships that consistently lead to conversations—even if customers cannot immediately move with them because of non-solicitation agreements.

Primary Responsibilities

• Develop new drayage business nationwide
• Prospect freight forwarders, importers, exporters, and BCOs
• Build executive-level relationships throughout the logistics community
• Generate new opportunities involving ocean container transportation
• Work closely with operations to ensure exceptional service execution
• Develop strategic sales plans for targeted accounts
• Help establish a scalable outside sales organization as the company continues to grow

Ideal Candidate Profile

Required Experience

• 5+ years of successful transportation sales
• Strong drayage sales experience
• Experience selling to:
  • Freight Forwarders
  • Importers
  • Exporters
  • Ocean shipping customers
• Demonstrated success generating new business
• Strong relationship-building skills
• Hunter mentality

Preferred Background

Experience with companies specializing in:

• Drayage
• Ocean Freight
• Freight Forwarding
• Container Logistics
• Import / Export Transportation
• Intermodal Transportation (bonus)

Personality

The ideal candidate:

• Is respected throughout the drayage community
• Can get meetings because of their reputation
• Understands the language of freight forwarders
• Is confident calling on Directors, VPs, and C-level executives
• Doesn't require constant supervision
• Is motivated by building something rather than simply managing accounts

What Success Looks Like

Within the first 90–120 days, the successful candidate should demonstrate:

• New executive meetings scheduled
• Active opportunities in the pipeline
• RFPs and quotations submitted
• Initial drayage loads moving
• Growing relationships with key freight forwarders and strategic customers

Management understands large accounts take time to develop but expects visible momentum early in the process.

Why Someone Would Join 

• One of the industry's strongest drayage platforms
• National drayage capabilities across every major U.S. port
• Established relationships with many of the largest global freight forwarders
• Proprietary technology purpose-built for drayage operations
• Family-owned company with long-tenured employees
• Entrepreneurial leadership
• Opportunity to build and shape the outside sales organization
• Opportunity for future leadership responsibilities as the company grows

Based on:

• Industry experience
• Existing relationships
• Leadership capability
• Ability to build a sales organization

Incentive Plan

Performance-based commission structure designed specifically for outside enterprise sales professionals, with additional upside available for individuals who eventually build and lead a sales team.