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.
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Hook up, secure, and haul roll-off containers and rental equipment safely across assigned routes.
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Operate under all applicable state and federal transportation regulations, maintaining impeccable safety and compliance.
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Maneuver truck and trailer with precision in tight yards and on active jobsites; follow spotter and crew signals.
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Assist with loading/unloading using appropriate gear; return skids and tools to their designated areas.
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Capture and hand off delivery paperwork—signed invoices, bills of lading, and route documentation—without delay.
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Perform basic truck care: check oil, coolant, fuel, and air; promptly report issues to the Shipping Supervisor.
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Reposition trailers in the yard to optimize loading patterns and turnaround times.
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Tackle additional tasks that keep the branch and fleet moving forward.
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.
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Monthly Family Dinner Night for you and your family (employee favorite; restrictions apply)
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Competitive pay
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Full medical, dental, and vision (full-time)
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Generous PTO plus paid holidays
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401(k) with company match
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Tool and boot reimbursements (role dependent)
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Gym stipend and wellness programs (earn PTO and prizes)
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Company events, food truck nights, and monthly dinners
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16 hours paid volunteer time annually
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Career growth, leadership training, and professional development
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Professional, courteous communication with customers and teammates at delivery points.
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Ability to stay focused and efficient in a fast-moving environment.
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Valid Class A CDL or chauffeur’s license (per state and vehicle weight requirements).
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Must pass DOT physical; trucks operated are over 10,000 lbs.
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At least 21 years of age to operate company vehicles.
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Extended periods seated in the cab.
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Lift and move up to 40 pounds.
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Frequent travel between customer sites and the branch.
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Clean shaven when required by specific customer sites.
EquipmentShare is an EOE M/F/D/V.
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.
