Roll-Off CDL Delivery Specialist -- Construction Equipment Transport

Job Description

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.