Roll-Off CDL Delivery Specialist — Construction Equipment Transport EquipmentShare - USA Milwaukee, WI Job Details Full-time $28 - $36 an hour 20 hours ago Benefits Paid holidays Health insurance Dental insurance Paid time off Leadership training provided Vision insurance 401(k) matching Gym membership Qualifications Customer communication DOT Physical Certification Full Job 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.