Transportation Operations Assistant Jobs in Milwaukee, WI

The Operations Assistant plays a critical role in maintaining the speed, accuracy, and reliability of day-to-day terminal operations. This position exists to ensure freight flows without disruption, operational data remains accurate in real time, and cross-functional teams are aligned on execution.
In a fast-moving logistics environment, even small delays or communication gaps can create downstream inefficiencies. This role directly mitigates those risks by owning load visibility, coordinating with multiple internal and external stakeholders, and ensuring operational systems reflect ground truth.
Success in this role means shipments move predictably, exceptions are identified and escalated early, and the service center operates with precision, accountability, and minimal rework. What you'll do1. Drive operational coordination and load visibility

• Track outbound loads daily and ensure system updates are accurate and timely
• Proactively communicate delays to leadership and cross-functional stakeholders before 11 AM
• Monitor pickup schedules and investigate loads that have not departed by 10 AM
• Escalate operational risks and delays to Linehaul and leadership with clear context

2. Execute administrative and documentation workflows

• Manage driver documentation, including IC paperwork, plates, IFTA, and compliance materials
• Collect and route maintenance records to Safety to ensure compliance standards are met
• Manifest inbound and outbound freight, ensuring documentation accuracy across systems
• File and maintain exception reports and operational records

3. Support delivery execution and customer commitments

• Schedule delivery appointments, including direct deliveries and diverts
• Coordinate redeliveries and obtain ACR (Additional Charge Request) authorization
• Enter ACRs into systems with precision to ensure financial and operational alignment
• Partner with brokers to secure rates for non-service point returns

4. Resolve operational exceptions and improve throughput

• Trace freight and investigate shipment issues across terminals and agent networks
• Coordinate with internal teams and external partners to resolve delivery disruptions
• Identify recurring issues and escalate patterns that impact service performance
• Support all terminals with system-related and operational inquiries

5. Maintain operational infrastructure and team efficiency

• Monitor functionality of printers and administrative equipment within operations
• Provide general administrative support including data entry, filing, imaging, and reporting
• Preset appointments for inbound freight and linehaul contractors
• Contribute to team-based operational goals and continuous improvement efforts

What you bring

• High school diploma or GED required; equivalent experience considered
• 1-3 months of relevant administrative or operations experience preferred
• Strong written and verbal communication skills with the ability to interact across all levels
• Basic computer proficiency; familiarity with AS/400, Microsoft Office, and imaging tools preferred
• Foundational math skills and comfort working with weights, distances, and monetary values
• Ability to read, interpret, and follow written and verbal instructions
• Strong organizational and prioritization skills in a fast-paced environment
• Capacity to manage multiple tasks simultaneously with attention to detail
• Problem-solving ability in situations with limited standardization
• Hazardous Materials Handling certification preferred
• Experience in transportation, logistics, or terminal operations is a plus

How you operate

• You prioritize accuracy without sacrificing speed
• You take ownership of outcomes, not just assigned tasks
• You communicate early, clearly, and with purpose
• You thrive in structured environments but can adapt when conditions shift
• You stay organized and focused under operational pressure
• You collaborate effectively across functions to resolve issues quickly
• You approach problems with practicality and a solution-first mindset

Compensation & Setup

• Pay: $18.00 to $20.00 per hour
• Location: Onsite - Milwaukee, WI
• Benefits: Full benefits package including medical, dental, vision, 401(k), and paid time off

Physical Demands and Work Environment

The physical demands and work environment described here are representative of those an employee encounters while performing the essential functions of this position. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.

Physical Demands

• Light physical activity performing non-strenuous daily activities of an administrative nature.
• While performing the duties of the job, the employee is regularly required to sit, stand, walk, reach/handle items, work with fingers, have color vision (ability to identify and distinguish colors) and talk and hear others in conversations via the phone or in person.
• The employee is occasionally asked to stoop, kneel, crouch, crawl, climb or balance and lift objects up to 25 lbs.

Work Environment

• The noise level is loud based on multiple printers and forklifts running outside of the door.
• Works in well-lighted, heated and/or air-conditioned indoor office setting with adequate ventilation.
• Might be required to occasionally work near toxic or caustic chemicals, moving mechanical parts and/or fumes or airborne particles.

* The above statements reflect the general details necessary to describe the principal functions of the position and are not intended to be all inclusive. The position and any of the requirements listed above are subject to change at any time according to the changing needs of the company.

* Roadrunner is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind.

* We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!

#LI-OnsiteMilwaukee, WI

About Roadrunner

Roadrunner is for ambitious, smart people who excel at execution over talking about it, and who would rather invent the next standard in freight than accept the status quo.

We are looking for the Best of the Best. Action driven leaders who want to be part of real change and help design the future of LTL in the U.S. This is a place where high performers can grow, influence outcomes, and make an impact while working directly with executives and smart people from across industries.

We bring a winner mindset. We take ownership, raise the bar, and measure ourselves by results. We Run Safe. We Run Smart. We Run Together. These principles create an environment of high standards, clear ownership, and direct collaboration. We trust data over intuition, move with urgency, and hold each other accountable because winning requires it.

Roadrunner exists to prove that LTL can be better than the industry has settled for. To be the best means we need to think bigger, look outside the box, and question every assumption: too many handoffs, limited visibility, and the quiet belief that "this is just how it works." We rejected that story. We built a proprietary Smart Network for direct, long haul, metro to metro service that delivers fewer touches, faster transit, real time visibility, and genuine accountability. We are the most tech forward company in LTL, and we are not finished widening the gap.

The foundation is already strong. Recognized as one of Built In Chicago's Best Large Places to Work. Earning top marks for improvement, quality, and service. The real opportunity is still ahead: helping invent what comes next.

If you want to be evaluated among the Best of the Best and help set the new standard in LTL, we should talk.