Sales Director/Executive of Drayage

Job Description
Job Description
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.