Roll-Off CDL Delivery Specialist — Construction Equipment Transport

EquipmentShare - USA

  • Milwaukee, WI
  • 10 days ago

    Highlights

    Join EquipmentShare in Milwaukee, WI as a Roll-Off CDL Delivery Specialist and help move the machines that keep jobsites running. Maneuver truck and trailer with precision in tight yards and on active jobsites; follow spotter and crew signals.

    Numbers & Facts

    LocationMilwaukee, WI

    Description

    Drive the Future of Construction Logistics

    Join EquipmentShare in Milwaukee, WI as a Roll-Off CDL Delivery Specialist and help move the machines that keep jobsites running. Your day starts at 7:00 AM, syncing your route on our T3 platform. You’ll roll out with real-time work orders, GPS-guided stops, and instant updates so you can deliver on time, every time. The schedule is Monday–Friday, 7:00 AM–5:00 PM, with overtime after 40 hours and occasional on-call assignments with added compensation.

    What a Day Looks Like

    • Hook up, secure, and haul roll-off containers and rental equipment safely across assigned routes.
    • Operate under all applicable state and federal transportation regulations, maintaining impeccable safety and compliance.
    • Maneuver truck and trailer with precision in tight yards and on active jobsites; follow spotter and crew signals.
    • Assist with loading/unloading using appropriate gear; return skids and tools to their designated areas.
    • Capture and hand off delivery paperwork—signed invoices, bills of lading, and route documentation—without delay.
    • Perform basic truck care: check oil, coolant, fuel, and air; promptly report issues to the Shipping Supervisor.
    • Reposition trailers in the yard to optimize loading patterns and turnaround times.
    • Tackle additional tasks that keep the branch and fleet moving forward.

    Why You’ll Love It Here

    We’re a people-first, tech-powered team. Our proprietary T3 platform streamlines your day and gives you the tools to work smarter and safer. You’ll be part of a crew that values problem-solvers, builders, and doers—people proud to make an impact.

    Perks & Benefits

    • Monthly Family Dinner Night for you and your family (employee favorite; restrictions apply)
    • Competitive pay
    • Full medical, dental, and vision (full-time)
    • Generous PTO plus paid holidays
    • 401(k) with company match
    • Tool and boot reimbursements (role dependent)
    • Gym stipend and wellness programs (earn PTO and prizes)
    • Company events, food truck nights, and monthly dinners
    • 16 hours paid volunteer time annually
    • Career growth, leadership training, and professional development

    What You Bring

    • Professional, courteous communication with customers and teammates at delivery points.
    • Ability to stay focused and efficient in a fast-moving environment.

    Licenses & Experience

    • Valid Class A CDL or chauffeur’s license (per state and vehicle weight requirements).
    • Must pass DOT physical; trucks operated are over 10,000 lbs.
    • At least 21 years of age to operate company vehicles.

    Physical Demands

    • Extended periods seated in the cab.
    • Lift and move up to 40 pounds.
    • Frequent travel between customer sites and the branch.
    • Clean shaven when required by specific customer sites.

    Compliance & Notices

    Equal Opportunity

    A Workplace For All

    EquipmentShare is an EOE M/F/D/V.

    Background Check and Drug Testing

    Education and Experience:

    • Must pass background and drug testing as required by federal and/or state department(s) of transportation regulations

    Physical Requirements:

    • This is a safety sensitive position and any offer of employment will be contingent on passing a 10 panel drug screen

    Employment is contingent on passing a background check. Additionally, some roles require passing a drug test, depending on the job responsibilities.

    Ready to put your CDL skills to work building what’s next? Apply today and drive with EquipmentShare.

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