Independent Contractor Payroll Jobs in Addison, IL

Dispatch Supervisor

Berkeley, IL

About Odyssey Logistics

Odyssey Logistics is a global logistics and supply chain partner helping businesses optimize performance through fully integrated, end-to-end solutions. We connect transportation, technology, and expertise across a broad network of services including 3PL and 4PL managed services, multimodal and intermodal transport, warehousing, trucking, Jones Act Ocean, and customs brokerage, ensuring goods move reliably, efficiently, and intelligently around the world.

Today, Odyssey supports more than 6,000 customers globally, delivering scalable, data-driven solutions across complex supply chains. What started with a single client has grown into a dynamic, evolving organization focused on performance, precision, and long-term partnership.

What Sets Us Apart:

Our work is complex, fast-moving, and highly collaborative. Success here requires people who think strategically, operate with urgency, and navigate across functions to solve real business challenges. We value individuals who take ownership, challenge the status quo, and turn insight into action.

Our culture is grounded in five core values: Win Together, Innovate Boldly, Drive Results, Customer Centric, and Guide with Care. These are not just principles; they shape how we make decisions, partner with customers, and show up for each other.

At Odyssey, you are not just part of a company; you are part of building what comes next.

The Role:

Work Model: On-Site
Work Schedule: The position requires an average of 45–50 hours per week and includes rotating after-hours and weekend on-call responsibilities.
Travel Requirements: Approximately 15%
Supervisory Responsibilities: Yes
Reports to: Director of Trucking Operations

Summary / Primary Role:

The Dispatch Supervisor is responsible for coordinating the scheduling and movement of shipments for multiple customers while directly supervising assigned Class A drivers. This position oversees daily dispatch operations, customer communication, shipment tracking, driver performance, and transportation coverage to ensure safe, efficient, and reliable service.

The Dispatch Supervisor also supports driver hiring, training, performance management, and compliance while working closely with customers, carriers, operations, maintenance, and human resources to achieve business and customer service objectives.

What You’ll Do:

As a Dispatch Supervisor, you will oversee daily transportation and dispatch operations while ensuring customer needs, driver performance, and operational goals are consistently met.

Dispatch & Transportation Operations

• Coordinate pickup and delivery schedules with customers and drivers.

• Dispatch loads and monitor shipments from pickup through delivery.

• Plan transportation routes, payloads, equipment requirements, and transportation modes.

• Track shipments and provide timely status updates to internal and external customers.

• Optimize the use of company drivers, Independent Contractors, and external carriers.

• Ensure freight is positioned appropriately to maximize driver productivity and revenue.

• Consider cost reduction, freight savings, service requirements, and contractual obligations when planning transportation.

• Coordinate the retrieval of equipment or loads in situations involving breakdowns, accidents, or abandonment.

Customer & Carrier Relationships

• Serve as a primary point of contact for customer, carrier, and driver-related issues.

• Establish and maintain strong relationships with customers, carriers, and drivers.

• Resolve logistical and service-related issues professionally and efficiently.

• Ensure customer service expectations and transportation coverage requirements are consistently met.

• Maintain accurate customer, vendor, carrier, and shipment information.

• Ensure required documentation is completed accurately and on time to support billing, payroll, and accounts payable processes.

Driver Leadership & Performance

• Directly supervise assigned Class A drivers and provide ongoing guidance and support.

• Assist with driver hiring, onboarding, orientation, and training.

• Monitor and document driver performance and provide regular feedback.

• Conduct driver performance reviews and developmental conversations.

• Address issues related to late deliveries, compliance, communication, paperwork, and service performance.

• Partner with Operations and Human Resources to support driver retention and growth strategies.

• Ensure drivers understand and comply with freight securement, permit, safety, and operational requirements.

• Report accidents, incidents, claims, and service failures to the appropriate HSSE team.

Technology & Operational Excellence

• Maximize the use of GPS, satellite tracking, Hours of Service (HOS), and other transportation technologies.

• Maintain accurate customer, carrier, driver, and operational records within company systems.

• Troubleshoot and correct common daily software issues.

• Monitor and report driver, customer, carrier, and operational performance metrics.

• Identify opportunities to improve transportation efficiency and logistics operations.

• Work closely with Maintenance to support proper pre- and post-trip inspections and preventative maintenance.

• Participate in operational meetings and provide recommendations to support revenue growth and business continuity.

• Provide additional operational support during employee vacations, absences, and periods of increased business activity.

• Participate in rotating after-hours and weekend on-call coverage for operational or safety-related issues.

What You Bring:

• High School Diploma or equivalent is required.

• 2–5 years of professional work experience is required.

• Previous experience managing drivers or transportation employees is required.

• Experience in transportation, dispatch, logistics, or trucking operations is preferred.

• Experience in warehousing is preferred.

• Proficiency in Microsoft Office software programs is required.

• Ability to type a minimum of 35 words per minute.

• Strong leadership, communication, and interpersonal skills.

• Strong organizational and time-management abilities.

• Excellent problem-solving and decision-making skills.

• Ability to manage multiple priorities in a fast-paced transportation environment.

• Strong customer service and relationship-management skills.

• Ability to work independently while collaborating effectively with customers, drivers, carriers, and internal teams.

• Ability to work flexible hours, including rotating after-hours and weekend on-call coverage.

Compensation & Schedule Details:

Base Pay Range: $55,000 – $65,000 annually
Bonus Eligible: No
Commission Eligible: No

As required by applicable Pay Transparency laws, Odyssey provides a range of minimum compensation for roles that may be hired in locations under these requirements. Factors that may be used to determine your actual salary may include a wide array of factors, including your specific skills and experience, geographic location, or other relevant factors. The salary range for this position may be lower or higher in different markets.

No relocation allowance will be considered unless specifically addressed. All applicants must be currently authorized to work in the United States.

Benefits:

We offer a comprehensive and competitive compensation and benefits package, including:

• A choice of medical plans with FSA and HSA options

• Dental Insurance

• Vision Insurance

• Company-paid Life and Disability Insurance

• 401(k) Plan with Company Match

• Paid Time Off (PTO) and Company Holidays

• Employee Assistance Program

• Company Health & Wellness Program

• Discounts with Preferred Vendors

At Odyssey, we believe the best ideas come from people with different skills, experiences, and perspectives. We welcome applicants from all backgrounds and evaluate every candidate based on the qualifications needed for the role, while also valuing the unique strengths, curiosity, and fresh thinking each person brings.

Our commitment to inclusion helps fuel innovation and enables us to deliver smarter, more creative solutions for our customers. We are proud to be a workplace where everyone is treated with respect, given equal opportunity to succeed, and encouraged to contribute in meaningful ways.

All employment decisions are based on merit, without regard to race or ethnicity, religion, color, sex, gender identity, sexual orientation, age, disability, national origin, veteran status, or any other characteristic protected by federal, state, or local law.

Odyssey does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or expression (including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances.

Visit us at: www.OdysseyLogistics.com/careers