Job title
Trucking Manager
Reports to
Head of Operations
Position Status
Full-Time, Exempt
Why K-Five Construction Corporation?
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4th Generation Family Owned and Operated
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One of the Largest Asphalt and Concrete paving companies in the Midwest
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Established reputation of high-quality materials and craftmanship
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Collaborative Work Environment
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Safety centered work culture
K-Five Construction has an enduring commitment to innovation, quality, and sustainability, ensuring that the infrastructure we build not only meets, but exceeds the needs of generations to come. Join the team that will shape the roadways and communities of tomorrow. At K-Five Construction, there are opportunities for growth, a supportive work environment, and the chance to tackle some of the most challenging and rewarding projects in the field. With the best talent, equipment, and technology in the industry, K-Five is a world-class place to grow your career and see the impact of your work in Chicagoland and beyond.
Job purpose
The Trucking Manager oversees trucking operations for K-Five Construction Corporation, including fleet management, equipment transportation, fuel operations, and broker relationships. This role ensures safe, efficient, and cost-effective delivery of equipment and materials to jobsites while maintaining DOT compliance and managing Teamster union relations.
Duties and responsibilities
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Coordinate daily equipment orders and dispatch lowboy trucks for day/night operations; secure OSOW permits; verify routes and weight limits; outsource transportation when needed.
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Monitor company trucks using Fleetwatcher system; maintain equipment inventory knowledge; coordinate with shop on repairs and equipment needs.
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Dispatch fuel trucks to jobsites with optimized routes; determine appropriate fuel types; negotiate fuel prices; manage vendor relationships and forward purchasing.
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Dispatch prime deliveries to jobsites; communicate quantities to plants; determine when outsourcing is cost-effective; maximize driver productivity.
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Establish seasonal dispatch targets; maintain relationships with trucking brokers; negotiate competitive rates; resolve daily disputes; approve broker invoices.
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Oversee CDL employee files and DOT paperwork; monitor license and medical card expirations; coordinate drug screens; maintain FMCSA Portal compliance.
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Handle union-related issues; oversee Teamster payroll and timesheets; maintain contract knowledge; greet drivers daily to address concerns.
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Provide trucking prices to estimating; fulfill minority trucking requirements; handle overweight fines; track permits for accounting.
Qualifications
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5+ years in trucking operations management, preferably in construction with heavy equipment transportation experience.
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Valid CDL with clean driving record; thorough knowledge of DOT regulations and OSOW permitting.
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Experience with Teamster unions and labor relations.
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Proficient with fleet management systems (Fleetwatcher or similar) and Microsoft Office.
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Understanding of construction equipment, fuel management, route planning, and transportation logistics.
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Strong negotiation and interpersonal skills for managing drivers, brokers, and internal departments.
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Must be available 24/7 for operations; strong problem-solving abilities and detail-oriented.
About Us
K-Five Construction is a fourth-generation family-owned business based in Chicagoland. We specialize in general contracting, asphalt and concrete paving, and material production, and are one of the largest contractors in the region. We are committed to sustainable practices and have been a leader in green construction for many years.
Working conditions
Employee will be working in a shop environment and assigned a workstation. On occasion, they will be required to attend offsite meetings or site visits.
Direct reports
This position has supervisory responsibility for an average of 3 to 5 office staff and 25 to 30 truck drivers.
